Khalid ibn-al Walid and the Fog of Late Antiquity
A lack of source material stifles historical understanding of Late Antiquity, a period whose massive impact is often lost on us. This dynamic also erases many important figures from mainstream historical discussion, none moreso than Khalid ibn-al Walid, potentially the single greatest military commander of all time. Who was Khalid ibn-al Walid? What does his life tell us about the chaotic world he was born into, the improbable spread of Islam, and the making of the modern Middle East?
The Context
There is no greater victim of Late Antiquity than Khalid ibn-al Walid.
First off, who was he? In simplest terms, Khalid ibn-al Walid was the most important and successful general in the Muslim Conquests. Largely through his victories and skill, the early Islamic Caliphate militarily expanded from the area around Medina, Saudi Arabia to control much of what is today considered the Middle East. He has a resume of military victories that are stunning in their improbability, scale, and tactical brilliance. In my opinion, he is the greatest general of all time. However, if you go look up “greatest general of all time”, he’s not going to come up as the guy. Some more well-studied people might have him in their top 5 or 10, but never at number 1. I sincerely believe that this isn’t because other candidates for the top spot have a better resume, it’s because Khalid is sunk by the understudied, badly sourced, chaotic time period he lived in.
Late Antiquity, often referred to in the past as the “Dark Ages” is a generally poorly-defined historical period, roughly lasting from the late 3rd Century CE to around the beginning of the 8th Century. Some place the early Muslim Conquests as the end point of Late Antiquity, but there is little consensus among historians. Reflecting its disjointed definition, Late Antiquity is also known for a lack of historical sources, widespread chaos, and the breakdown of the empires, economies, and systems of governance of Classical Antiquity. Essentially, everyone was so busy trying not to die to write about anything. Some of the only well-known figures among casual fans of history (in the Western world) to come out of Late Antiquity are Justinian, Belisarius, Theodora, and of course, the Prophet Muhammad. Essentially the only figure not connected to the Byzantine Empire is Muhammad himself, and he mainly survives through scripture. Written sources of this period are so limited that wide swathes of what was happening across Europe and the Middle East (normally the most well-sourced regions) will never be known.
I love Late Antiquity. The mystery makes it just so intriguing, and I really, really hope that one day someone uncovers something that tells us where exactly the Avars came from or what the Lombards and Vandals were up to. Maybe someday some unfound source will give us as deep a look into Sassanid Persia as we have for the Byzantine Empire. This will likely never happen, and that mystery and haziness will forever make Late Antiquity under-publicized and take guys like Khalid ibn al-Walid out of discussions, history courses, and Top 10 lists of historical generals.
The Fall of Rome and the beginning of Islam are the seismic events of Late Antiquity. The Fall of Rome has been analyzed to death and is often placed in Classical Antiquity, but in the West the spread of Islam is mostly looked at simplistically, even in the advanced history books and courses I’ve come across. I can’t tell you how many times I’ve seen the jump from “Muhammad had a revelation in 610 AD” to “the Rashidun Caliphate controlled nearly the entire Middle East in 660 AD.” What happened in between? Muslims already know, but the incredible achievements that made that happen are glaringly under-told in military and world history because of the time period they happened to take place in. It’s an incredible, improbable story of military conquest against all odds and the mainstream instinct is, somehow, to gloss over it. How can we really claim to study history if we don’t study how the second-largest religion in the world made it out of the deserts of Arabia? Why don’t we really take a second to contemplate the amazingly long odds of that happening?
I consider the Muslim Conquests to be the greatest left turn in geopolitical history.
I’m going to set the scene with an incredibly oversimplified, somewhat exaggerated metaphor: imagine it’s the Cold War. The US and USSR actually fight a conventional war with each other, directly, over the course of decades. They essentially pummel each other to a stalemate, with the US able to claim a costly victory. Both countries are weakened, but still control their vast empires. As they begin to rebuild, Ecuador, who has a far smaller army, less resources, and who neither had seen as a threat until this point, comes out of absolutely nowhere to completely conquer the USSR and invade the US. The US is able to keep the Eastern Seaboard but loses the rest of the country to Ecuador, who unsuccessfully lays siege to Washington D.C a few times. This is, in my mind, the closest hypothetical parallel to the Muslim Conquests. There are no real-world historical parallels because of the sheer improbability of what happened.
In my metaphor, the Byzantine Empire and Sassanid Persia in 630 AD play the role of the US and USSR, while the early Caliphate plays the role of Ecuador. In order for Islam to break out of the Arabian peninsula and go anywhere, the Caliphate had to defeat the two greatest empires of its time period in succession. This makes the early decades of Islamic history largely military-focused, and a large part of the reason for Islam’s survival and spread the military prowess of its armies. I mean this purely in a geopolitical sense, not a spiritual one. While the early Caliphate spread through military conquest, Islam has obviously not only spread by the sword. However, I would assert that without incredible military leadership in the crucial early decades of Islam’s spread, there is little chance it would have become the worldwide religion it is today.
Telling the story of the Muslim Conquests through Khalid ibn-al Walid does not encompass their full scope by any means. However, I think we can easily connect the extreme changes brought about through his military successes to the composition of the modern Middle East. I’m fully aware that pure military or Great Man history isn’t the best means to fully analyze and understand an entire time period or a change on this scale, and that’s not what I’m trying to do. If anything, Khalid actually presents a counterpoint and shows the limits to the Great Man Theory: he isn’t put on the pantheon of historical changemakers in the West because his time period and life aren’t deemed important. For the most part, I’m just trying to bring forward the story of a man who is drastically given the short end of the stick by the Western historical tradition. His life contains a lot of truly insane achievements and events, and also, admittedly, a lot of points where I can segue into talking about things in Late Antiquity that intrigue or bother me.
I’ll also acknowledge that this is my take on what probably happened, based on my judgment and the information available to me. I definitely don’t think I got everything right, and I’m just trying to synthesize conflicting information in a way that makes sense to me and hopefully to you. There are various parts of this narrative that historians still fiercely debate over, and new discoveries about events of this period are constantly happening. History is not a clear-cut thing, and its study is ever-changing. Late Antiquity’s unsolidified narrative leaves even more room for debate, revision, and discovery. No one has anything in Late Antiquity completely down, but some people are closer than others to knowing. I am not one of the closest, as I am not a professional historian. Still, I can bring forward a lot of information that doesn’t get taught in our history classes and give you a healthily skeptical narrative about it.
I’d also like to add that I’m talking from the perspective of an American and referring to the history which has been taught and made easily accessible to me as “Western” and “mainstream”. It’s the historical mainstream for me and others like me, not for everyone. If you’re Muslim, or from what we consider the greater Islamic World, I’m sure you know plenty about this and it was all a much bigger deal in your historical tradition. Still, I absolutely welcome you along for the ride. It’s quite a crazy one.
The Early Years
What was Khalid ibn-al Walid, this giant of a historical figure, up to as a kid and young man? Great question! No one knows. Welcome to Late Antiquity.
What we do know is the clan and tribe Khalid ibn al-Walid was a part of, which explain his allegiances at the beginning of his military career. Khalid was a part of the powerful Banu Makhzum clan, one of the leading clans in the polytheistic Quraysh, the confederation which ruled Mecca and its surrounding areas at the inception of Islam. His family was clearly a powerful force in its clan, the Quraysh, and Mecca in general, as many members of its are recorded as prominent political figures. Khalid himself has been noted by historian Muhammad Abdulhayy Shaban as a “man of considerable standing” in Mecca. The Makhzum in particular are remembered for being a clan who stringently opposed Muhammad and his followers, playing a leading role in driving him out of the city.
Khalid enters the historical record with a bang in 625 AD at the Battle of Uhud. How old was he? Another good question! Maybe around 30, but also maybe around 45. Isn’t this fun? It’s somewhat difficult to believe that the Battle of Uhud was the first battle he ever fought, but it is where he made his name and kicked off an incredible string of achievements. He started his military career loyal to the Quraysh, commanding a flank of their army against Muhammad and his Muslim followers. Accounts of this battle widely differ, but it seems that the Quraysh heavily outnumbered the Muslims. Against the odds, the Muslims were on the verge of routing the Quraysh when Khalid swung the troops in his command around the Muslim flank and attacked them from the rear, salvaging a narrow victory for the Quraysh.
Khalid disappears from the record for a few years after this, but was clearly on Muhammad’s radar as a skilled and fearsome commander. After the Quraysh and Muslims signed a peace treaty in 628 AD, he reemerged to make perhaps the most important decision of his life. Khalid abandoned Mecca and “embraced Islam in Muhammad’s presence.” It’s difficult to know if his motivations were purely spiritual or more of a pragmatic choice, but that’s not the important part of the story. Khalid’s conversion to Islam is one of those little events that no one really considers the significance of. In one stroke, Islam gained its greatest general ever at the exact point when they needed him most.
From this point on, Khalid ibn-al Walid embarks on perhaps the greatest decade of military brilliance in human history. It’s impossible to go over everything he did, so I’m going to focus on some of his most pivotal and impressive battles. Khalid is estimated to have fought about 40 battles, 30 of which he was the primary commander. He didn’t lose a single one. I’m going to go over his most important campaigns and his particularly impressive achievements, but please note that this isn’t describing every achievement or success of his. There are plenty of great biopics of Khalid ibn-al Walid out there that will more thoroughly analyze this period.
The most notable of Khalid’s early campaigns as a Muslim general is the Mut’ah Expedition. Even in the context of Khalid’s achievements, which are already very overlooked, this expedition is not highlighted often. However, Khalid truly shines in perhaps the most dire and dangerous situation of his life, showing his quick thinking and ingenuity in the face of danger.
After peace was concluded with the Quraysh, the Muslims turned north, looking to expand and convert peoples in the northern part of the Arabian Peninsula and southern Levant. This area was occupied by the Ghassanids, a Christian Arab tribe which was allied with the Byzantine Empire. At some point, relations between the Ghassanids and Muslims became hostile, with Byzantine and Islamic sources each shifting blame for the conflict to the other side. The Byzantines, contrary to many narratives, were not asleep at the wheel during the rise of Islam. They saw the storm brewing in Arabia and seized upon the earliest opportunity to crush it by greatly reinforcing the Ghassanid army. The Ghassanid/Byzantine and Muslim armies met near Mut’ah (in present-day Jordan) in 629 AD. While troop numbers for the Muslim Conquests are notoriously unreliable, modern-day estimates place the Ghassanid/Byzantine army at around 10,000 troops and the Muslim army at around 3,000. The Byzantines quickly gained the upper hand, and after the three primary commanders for the Muslim armies were all killed, command passed to Khalid ibn-al Walid. Outnumbered and with his army on the brink of annihilation, Khalid had to figure out a way to retreat to Medina with the army intact.
After the initial battle concluded, Khalid knew the Byzantines had every opportunity to crush his army if they realized how dire of a situation the Muslims were in. He proceeded to concoct one of the all-time military tricks, the type that establishes a military commander not just as skillful but as genius. It may not be their greatest or most impactful victory, but it’s perhaps the most mind-blowing achievement of theirs for future readers. There’s always an element of danger and trickery involved (examples of this are Caesar building a second wall at Alesia or Alexander psyching out the Illyrian tribes by doing military drills).
So what exactly did Khalid pull off to outsmart the Byzantines and get his army to safety? It centered around making the Byzantines believe that Muslim reinforcements had arrived, thereby getting them to hold off from attacking. Khalid completely changed his troop formations overnight, moved parts of his army around surrounding mountains and hills, and purposefully made lots of noise while doing so. He also switched out the banners the troops being moved around were holding, adding to the illusion that new troops had arrived. This even extended to more minute details, such as ordering his cavalry to kick up as much dust as possible to insinuate that they were moving in far greater numbers. The Byzantines were successfully deceived and hesitated to attack. Khalid took the opportunity to bolt and got his army to safety, successfully retreating to Medina. After his return, Khalid was allegedly rewarded by being given the honorary title “Sword of Allah’’ by Muhammad.
The next few years of Khalid’s career were centered around consolidating Muslim control of the Hijaz and surrounding areas. He spread Islam to tribes in the area which had not yet converted, and most notably commanded part of the Muslim army which finally captured his birthplace of Mecca in 630 AD. Details are scant, but Khalid continued to build his reputation and helped Islam spread further around the Arabian Peninsula by converting tribes through both diplomacy and the sword. He is especially associated with commanding nomadic Bedouin contingents of Muhammad’s army in this time period.
After Muhammad’s death in 632 AD, the Rashidun Caliphate was established with Abu Bakr as the first Caliph. Muhammad’s death led to the loss of Rashidun central authority over many of the converted tribes outside of the Hijaz, with many people claiming themselves to be prophets, the real successors to Muhammad, or attempting to break away from Islam entirely. Khalid sided with Abu Bakr and the Caliphate and he would be essential in uniting the entire Arabian peninsula under Rashidun authority. These fights to consolidate power were known as the Ridda Wars, and the fact they only lasted around a year is another testament to Khalid’s brilliance.
The Ridda Wars are a bit messy, and the details aren’t incredibly consequential when it comes to the early history of Islam, only the results. Essentially, rebel support consolidated around a few tribal leaders, some of whom claimed to be prophets. Khalid was dispatched to defeat these rebel tribes in succession, which he did. These were not easy battles, and Khalid won many of them with heavy losses or concluded peace deals with concessions from both sides. Still, he succeeded in bringing all who he campaigned against back under Rashidun authority, while other commanders succeeded in their campaigns to spread the Caliphate across the entire Arabian peninsula.
It’s here that we start to see some detractors of Khalid arise, as well as some potential marks on his resume. In defeating a few rebel leaders, his conduct is described as being on the harsh side, especially executing some defeated rebels over the appeals of other Muslim leaders. Perhaps the greatest mark is his execution of the rebel leader Malik ibn Nuwayra, after which he proceeded to marry Malik’s widow. Killing a guy and then marrying his widow is generally frowned upon, and one guy who particularly didn’t like it was Umar, the eventual successor to Caliph Abu Bakr. This would go on to be a big deal in the future. With that being said, I don’t really think Khalid’s conduct was especially bad in terms of 7th Century warfare. In fact, I’d probably describe it as somewhat lenient in terms of putting down a rebellion, but he does get knocked in some contemporary sources because these actions were done to fellow Muslims. Scars from the Ridda Wars ran deep for a while, and Khalid being the face of the effort to subdue other Arabian tribes made him some permanent enemies and got him written out of some sources. This might be a contributing factor for his lack of fame. At the same time, it also isn’t the only bad press Khalid ever got, and as a whole his good press definitely overwhelms the bad. We’ll probably never know how much Khalid’s “bad” actions in the Ridda Wars and beyond were twisted and exaggerated by his detractors, but it is an interesting point to open historiographical questions about the man. It’s also another point where we should remember perhaps the most important principle of studying history: nothing is 100% straightforward and no account is 100% accurate. Everyone has their own motives for telling a story a certain way. As I’ve established before, this especially applies to the chaotic landscape of Late Antiquity.
The Fall of Persia
It’s at this point that Khalid ibn-al Walid enters the most legendary phase of his career. Those two superpowers I mentioned earlier are about to enter a world of trouble.
It’s Sassanid Persia’s turn first. Persia, one of the pre-eminent states and civilizations of the world for a millennium running before 634 AD, to this day has never recovered the relative geopolitical power it held before Khalid ibn-al Walid showed up on its doorstep. That’s not to say that Persia (Iran) isn’t still incredibly important. Today, the fact Iran is a Muslim country is especially important, being the only official theocracy on Earth. The fact it’s also predominantly Shia Muslim is crucial, leading to deep sectarian conflicts with its neighbors and shaping the political landscape of the Middle East. It’s possible some of these things play in a similar way if Khalid ibn-al Walid doesn’t exist, but it was he who set in motion the dominance of Islam in the region.
For a newly formed state in Arabia, regarded in this time period as an unimportant backwater, the idea of conquering Persia should have been as inconceivable as my dog writing a thesis on the intricacies of French mercantilist policy in the 17th Century. It’s interesting to wonder how much of the supreme confidence of the Rashidun Caliphate came from theological justifications, and how much came from having a guy like Khalid at their disposal. I think the early Rashidun state likely attempts to expand out of Arabia at some point either way due to their theological obligation to spread Islam, but probably not so quickly or so boldly if they don’t have the greatest general of all time fighting for them. This boldness is essential, because they managed to catch Sassanid Persia in quite a vulnerable state. A few years after being ravaged by the most brutal and iconic war of Late Antiquity against the Byzantines, they were in the throes of serious political turmoil and not nearly as unified as they should have been. New administration was righting the ship, but not quickly enough. Did I forget to mention that they had also been hit with a devastating plague a few years before? Yeah, that also happened. It’s likely that if the Caliphate gives the Sassanids five more years to restabilize and consolidate central power, even the military brilliance of Khalid and his army would not have been enough to overcome them. With that being said, the Persians were still overwhelming favorites, fielding more troops, drawing on more resources, and fighting on their geographically advantageous home turf. This sense of their own power would prove to be another huge weakness for Sassanid Persia, as they were pretty cavalier about the first Muslim attacks and allowed Khalid some extra time to consolidate a foothold in their territory.
Khalid didn’t enter Sassanid territory with the idea, “I’m going to conquer Persia”, nor did he fully conquer Persia (spoiler alert). Most historians agree that he was there with the goal of spreading Islam and Caliphate control to the nomadic Arab tribes that occupied the fringes of Sassanid territory in modern-day Iraq (Mesopotamia). This, of course, brought him into conflict with the Sassanids. I would assert that in this somewhat incidental contact with the Sassanians, he did irreparable damage to their empire. While many consider Persia to be the territory of modern-day Iran, the Sassanids’ center of power was in Iraq. The most important cities of the empire were on or near the banks of the Tigris and Euphrates, including the capital Ctesiphon, the up and coming megacity of Baghdad, and the important centers of Hira and al-Anbar. Khalid is not going to deliver the killing blow to the Persians or march into Ctesiphon, but his campaign is going to be what makes that possible and leads to it inevitably happening under less skilled commanders. I would argue that he deserves a lot of credit for the Conquest of Persia, but not all of it. Enough about all that though, on to the fun part.
Khalid entered Iraq in 633 AD, right off the back of the Ridda Wars. What does a great general need? Initiative! In fact, some say Khalid might have taken a bit too much initiative here. Many historians claim that he didn’t even get authority from Caliph Abu Bakr to invade Sassanian territory, he just took his guys and went for it. Making this even more of a wild thing to do, a lot of his troops apparently went home because they were tired of fighting in the Ridda Wars and definitely weren’t keen to go straight to Iraq afterward. This foreshadows Khalid’s later brushes with authority and also gives us a lot better of an idea of what kind of a guy he was, as sources on his personality are basically nonexistent.
The first battle that would be fought between the Persians and Muslims under Khalid was called the Battle of Chains, and Khalid made sure it was won before it was even fought. Maneuvering around modern-day Kuwait, he correctly identified that the main weakness of the Sassanid army was their lack of mobility, as they fought and traveled in heavy armor. Considering it was April in an area known for incredibly hot climate, if Khalid could get the Sassanid army to chase him around for a bit he could exhaust them and strike when they were most vulnerable. He sent fake communications on his movements to Hormozd, the provincial governor and commander of Persian forces in the area, and essentially led him and his army on a wild goose chase. For the Muslim army, movement was never an issue as they traveled lightly and, interestingly, on camels. They even brought horses along with them to switch mounts when battle was joined. They were far faster and more mobile than the Persians, meaning battle could be initiated entirely on their terms. Khalid finally faced up with the Sassanid army at Kazima. Why was this called the Battle of Chains? Well, because the Persians had the interesting idea of chaining themselves to each other in order to prevent cavalry breakthroughs and show the Muslims that they would sooner die than retreat. This predictably went very badly. The full-strength Muslim army quickly overwhelmed the exhausted Persians to the point where a retreat was necessary. Most of the Persian army couldn’t retreat because they were chained together and therefore died, including Hormozd. This was one of the few battles where troop numbers were relatively even between Khalid and the Sassanids, at around 18,000 each. While we mostly look at Khalid through the lens of individual battles, this part of the campaign gives a good idea of how Khalid leveraged the few advantages his army had and crafted brilliant overarching strategies.
After defeating the Persians at Kazima, Khalid marched north along the Euphrates River, picking up converts to Islam who joined and supplemented his army. Khalid continued to utilize his strategy of mobility, attacking and defeating the re-forming Persian army at what’s commonly known as the Battle of the Euphrates River. The Muslims were probably outnumbered around 2 to 1 in this battle, and Khalid supposedly dueled and killed all three of the leading Persian commanders beforehand, leaving their army leaderless and ripe for defeat. These duels sound a bit unbelievable for my liking, but I had to mention it because if it did really happen then that’s so cool.
The Muslim army continued up the Euphrates, eventually meeting another two re-formed Sassanid armies and their Arab Christian allies at the Battle of Walaja. The Persians again outnumbered the Muslims, with their troops numbering somewhere between 20,000 and 30,000, and Khalid’s army numbering 15,000. Walaja is one of the finest victories of Khalid’s career, as he pulled off what’s known as a “double envelopment” of the Sassanid army. This involves feigning a retreat of your army’s center, drawing in the opponent’s army, and attacking it around both flanks. This tactic has only been successfully done a handful of times, most notably by Hannibal at the Battle of Cannae. Khalid showed even more ingenuity by hiding his cavalry on his flanks behind ridges in the Iraqi terrain, and calling them out to attack the Persian rear at the exact moment he had drawn the Sassanid army into a good position. Pulling off a double envelopment is a near-impossible thing to do, and many of the greatest generals of antiquity never managed to do it. Doing it while heavily outnumbered and utilizing an incredible move like hiding the cavalry behind the ridges is perhaps the height of military brilliance. The fact that Walaja probably doesn’t make the top 3 of Khalid’s greatest victories already shows us why he was the greatest military mind of all time.
Khalid proceeded to meet another re-formed Persian and Arab Christian army at Ullais, in between the Khaseef and Euphrates rivers. Sources on this battle are far more scant and probably a bit more unreliable than usual, as some claimed the Persian army numbered 70,000 (it was probably more like 30,000). Khalid’s army again clocked in at a consistent 18,000 troops. Still, it’s a testament to Persia’s might that even in the death throes of their empire they were able to put up such strong armies and replenish their forces with overwhelming manpower so frequently. What we do know about this engagement is that the Muslims won a crushing victory, pinning the Persians against the junction of the two rivers and completely destroying their army. The battle is often referred to as the Battle of Blood River due to the astonishing number of casualties on the Persian side making the Khaseef River run red. Many of those casualties were caused by Khalid ordering the entire captured Persian army to be beheaded after they surrendered, which isn’t a nice thing to do but also wasn’t exactly unusual in the context of 633 AD. This was probably the hardest-fought and most even battle of the campaign, as Khalid is recorded in one source as saying: “At Mut’ah I broke nine swords in my hand. But I have never met an enemy like the Persians. And among the Persians I have never met an enemy like the army of Ullais.”
With precisely five entire enemy armies crushed, Khalid was finally free to target the original strategic objectives of his campaign. He besieged and conquered al-Anbar, Hira, and ayn-al Tamr, taking some of the leading cities of Persian Iraq and dealing crippling losses to Sassanid power and morale. Presumably because he was bored or just loved marching north along the Euphrates, he kept moving, primarily fighting and defeating Arab Christian armies along the way. These armies were not up to par with the Persians, but some of them came into battle at equal strength to the Muslim force. After taking control of the entire west bank of the Euphrates from the Persian Gulf to the border with the Byzantine Empire, Khalid returned to Hira, where he would be called to move into his next and even more legendary chapter. Through this campaign, Khalid wiped out the best soldiers Sassanid Persia had to field, defeated or killed all of its most skilled commanders, crushed their Arab Christian allies and added their lands to the Rashidun Caliphate, and took three of the leading cities under Persian control. The manpower, morale, and economic losses sustained in this campaign were the crippling blow for Sassanid Persia, and when Muslim armies returned a few years later they would deliver the killing blow.
Bedlam in Byzantium
As for Khalid ibn-al Walid, he was riding high. Revered and famous in the entire Middle East by this point, he had just come off of a masterful campaign and could easily have pushed further into Sassanid Persia. However, Caliph Abu Bakr had other plans for him. He ordered Khalid to cross the desert and take over command of the Rashidun invasion of the Byzantine Empire, an even more menacing and powerful foe than Sassanid Persia. Abu Bakr did this by delivering an incredibly hard quote: “By Allah, I shall destroy the Romans (Byzantines) and the friends of Satan with Khalid ibn-al Walid.” Khalid is getting referred to as if he’s a nuclear weapon, and he hasn’t even won his greatest victory yet. Incredible. If I’m Khalid, I’m hanging that on my wall or something. There’s a good chance this quote was fabricated later on, but that’s for far better historians than me to judge.
The Byzantine Empire, or the Eastern Roman Empire, was the titan of Late Antiquity. In many ways, it’s still seen as a protagonist of the era in modern-day narratives. It’s hard to let the Roman Empire go, and the Byzantines are their less popular but still highly acclaimed sequel. The Eastern Roman Empire is known as such because it was the part of the Roman Empire that survived when the Western Roman Empire fell in 476 AD. Their capital was one of the most important cities in world history, Constantinople (modern-day Istanbul), and their empire would survive in one form or another until 1453. Very important guys, and what Khalid is about to do to their empire is crucially important in shaping the modern Middle East.
I’d like to sidetrack for a second to talk about the Byzantines and how they shape our views of Late Antiquity in greater detail. Certain parts of the Byzantine Empire’s heyday in the 500s are the only part of Late Antiquity one could reasonably say are well-publicized, and even those sources leave out huge swathes of history. Did you know that in the 540s, the bubonic plague struck the Near East and killed around as many people as the Black Death did in the 1300s? Probably not. Again, welcome to Late Antiquity. The Byzantines get the most limelight of this period through the reign of Justinian and their attempts to reconquer the territories of the Western Roman Empire, which is the extent of most casual history fans’ knowledge of Late Antiquity. They’re both victims and benefactors of this dynamic.
One on hand, despite being the flag carriers of Late Antiquity, the Byzantines still aren’t very well-known. These are the successors to the Roman Empire, doing lots of important stuff, and their reward is a select few people going “Oh yeah, Justinian, I know that guy.” Late Antiquity is perhaps the only historical period you can basically own and still not manage to be known about in the mainstream. You would think the surviving part of the Roman Empire, who stuck around for longer than the original Roman Empire, would get at least comparable publicity (especially considering they were more recent!). People in their time period called them the Romans, even. No such luck. It’s not like they were just sitting there either, they did tons of really interesting things, like setting the Crusades in motion. Still, it’s not too bad for them when we think about their legacy.
Among people who know about the Byzantine Empire, most think of them in an overwhelmingly positive manner. Justinian is seen as a great man, Belisarius and Narses as fantastic generals. The Byzantines get away with a lot because sources are very favorable to them and we don’t have a good look inside their enemies. The Sassanid Persians get bad press, the Ostrogoths get bad press, and the Byzantines were oh-so-righteous while these meanies kept attacking them. It erases the fact that the Byzantines were warmongers and oppressors a good portion of the time. Everyone roots for them in old accounts as they absolutely ravage Ostrogothic Italy for some good old revanchism, crush popular dissent in Constantinople, and generally cause suffering through political backstabbing and violence. The Roman Empire doesn’t get away with doing this, so why do the Byzantines? It’s because of the mystery, lack of opposing sources, and lack of mainstream knowledge of their empire. For people not studying history in depth, just knowing about the Byzantine Empire is 90% of the battle, so why take the time to scrutinize them? It’s not like Late Antiquity gives you much context to place them in. It brings up an interesting thread of thought: Would you rather be a lesser-known, positively-viewed figure with your flaws overlooked, or a monumentally famous figure but have your flaws scrutinized and dissected?
Enough with my tangent, back to Khalid.
Khalid’s march to Syria is another legendary part of early Islamic history which I’m not going to delve into too deeply. In the spring of 634 AD, his army marched through barren desert to avoid Byzantine forces, going along a route with no water and using camels for water storage. It was a daring and bold feat, allowing his army to maintain the initiative, make an immediate contribution to the invasion, and catch the Byzantines by surprise. In some accounts, the Muslim army was very close to dying of thirst before they came upon a spring of water, and some others claim the whole march was a fabrication. Whatever the case, Khalid took a very short time in getting to Syria from Iraq, adding to his legendary record of outmaneuvering his enemies. The Byzantines were not at all prepared for this, and would be on the back foot for quite a bit of the campaign as a result.
The Byzantines came into this encounter with Khalid in better shape than the Persians did, but not at their best. They were politically far more stable, still ruled by the legendary Emperor Heraclius, but had suffered grievously in their decades-long war with the Persians. Their manpower was still overwhelming and they had been allowed a few more years to recover than the Persians before being hit with the Rashidun onslaught. A lot of their power came down to the areas they controlled and that the Muslims were now attempting to take, some of the most fruitful, rich, and sophisticated in the world. Syria and the Levant were major trading centers and sources of wealth, dotted with some of the preeminent cities on Earth. They were strategically crucial in their location, comprising a gateway into the Mediterranean world and Europe. Also, quite importantly, they included the Holy Land. It goes without saying, but the Muslim Conquest of these lands has sparked animosity and war that has lasted ever since and will continue for the foreseeable future. The stakes in this campaign could not be much higher when it comes to how they impact the present day. Imagine a world where the Crusades never happened, the Ottoman Empire never existed, Jerusalem is Christian, or the Israeli-Palestinian conflict isn’t a thing.
Remember the Ghassanids? The Byzantine allies that gave Khalid a real scare back in the day? You know, that one time he had to fake receiving reinforcements and make a daring escape? Man, they sure seem like scary guys. Anyway, Khalid proceeded to delete their state from the map over the course of a few months. In a series of relatively small battles, his forces triumphed over the Ghassanids’ often larger armies (supplemented with Byzantine reinforcements), culminating in Khalid taking the Ghassanid capital of Bosra in July of 634 AD. The Byzantines had previously used the Ghassanid state (which comprised much of modern-day Jordan and Southern Syria) as a buffer with Persia, and in previous years to hold off the Caliphate. With them out of the way, the Muslims could move into the Syrian heartland.
The Byzantines were not taking this lightly at all, and had moved considerable forces to Syria and the Levant to combat the invasion. The first Byzantine army Khalid faced in battle was commanded by Theodore, the brother to Emperor Heraclius himself. In the vicinity of Ajnadayn, now located in modern-day Israel, Khalid and Theodore’s armies fought a drastically under-sourced battle which ended in a Muslim victory. Modern-day estimates place both armies at around 20,000 men. The limited knowledge we have of this battle points to it being a bloody affair, with Vardan, Theodore’s second-in-command, killed. Even contemporary Muslim sources, known for downplaying casualties on the Muslim side, state that the Rashidun army lost many men. It must have been a lot worse for the Byzantines, as they abandoned the area and left the Levant open to Muslim raids. Khalid is recorded to have taken a lot of cities and towns in the aftermath of the Battle of Ajnadayn, most importantly the coastal trading city of Jaffa.
The defeat of Theodore’s army left the road open to Damascus, and Khalid’s army smashed a small force sent to delay its advance. Damascus was held by Thomas, Emperor Heraclius’s son-in-law. While it would reach its height centuries later under Muslim rule, it was already an incredibly important city. Known as the “paradise of Syria”, it was a center of trade for merchants across the Middle East and boasted enormous wealth, as well as enormous fortifications. The Rashidun army numbered around 20,000, and was divided between six of Khalid’s commanders to besiege each of the six gates into the city. Khalid also deployed troops at points on the roads into Damascus to guard against any Byzantine relief forces. When a Byzantine relief force of 12,000 men sent by Emperor Heraclius overwhelmed one of these detachments, Khalid took all his cavalry from Damascus, rode out, and routed them. While this engagement is often grouped into the larger Siege of Damascus, it’s quite impressive nonetheless. Khalid’s cavalry only numbered 4,000 and he managed to drive off an army three times its size. It is often said that if Thomas had attacked the Muslim armies at his gates while Khalid was away with the cavalry, he may have broken the siege. He decided on this course too late. When his armies finally carried out a simultaneous attack through four of the gates, Khalid was able to take his cavalry around and reinforce each part of his army that was under the most threat. These attacks killed many of the Byzantine troops, and Thomas eventually capitulated in September 634. In barely a month, Khalid had taken one of the most important cities in the Middle East. As a part of the surrender agreement, Thomas’s army was allowed to leave the city and Khalid agreed that Muslim armies would not pursue it for three days. After taking the surprising and, honestly, pretty nice step of actually waiting the three days, Khalid chased down Thomas’s army with his more mobile cavalry and crushed it. Thomas was killed in the fighting, supposedly in a one-on-one duel with Khalid, eliminating another prominent and skilled Byzantine commander. Damascus would eventually become the capital of the Umayyad Caliphate, the state which succeeded the Rashidun Caliphate.
Coming off one of his greatest victories and having delivered the Caliphate its greatest city yet, Khalid ibn-al Walid was at the height of his prestige and popularity. That was about to come to an end. Remember how Khalid had angered Caliph Abu Bakr’s successor, Umar, with some of his conduct in the Ridda Wars? Remember how I said that would be important later? Well, it’s later, and now it’s important. Caliph Abu Bakr died in August 634, and was succeeded by Umar. Caliph Umar, an incredible man in his own right, was also Khalid’s principal hater. One of his first acts as Caliph was to demote Khalid and put command of his army into the hands of Abu Ubayda, another crucial figure in early Islamic history. Abu Ubayda thankfully was also an incredibly skilled military commander and possessed control of his ego that the Buddha would envy. This led to him keeping Khalid around and giving very heavy weight to his advice. Thankfully, some of the larger battles from this point on are also a lot more well-sourced, allowing us to pinpoint in closer detail what decisions Khalid was making.
It seems like demoting Khalid is an absolutely crazy decision, but it is important to see in context. As mentioned earlier, his conduct in the past had earned him some important detractors, but it wasn’t just this that people held against him. On a larger scale, he was just generally seen as being on the lesser end of piety among leading Muslim figures. Perhaps this was due to his somewhat freewheeling attitude toward religious doctrine, his roots in the Quraysh, or his association with the Bedouin tribes. A big reason he got in hot water in Syria was his ravenous pursuit of war loot and his very, very generous distribution of this loot among his troops, which made him no fans among austere figures in the Caliphate’s religious establishment. Khalid somewhat struggled in dealing with Caliphate authority, but he’s not incredibly unique in that respect. The Rashidun Caliphate was constantly dealing with threats to its authority, from the Ridda Wars to the incoming Sunni-Shia split. Still, as mentioned earlier, having very powerful adversaries within his own “side” probably did not do wonders for Khalid’s depictions and overall historical legacy, which may help explain why he’s not as well known as he could be today.
Thankfully, Khalid’s demotion is far from the end of his story.
While we’re away from the Byzantine campaign for just a second, I’d like to engage in some rudimentary historiography, because the study of this campaign is in the process of undergoing some serious changes. As I’ve established, lots of arguments are happening or have happened between historians about what was really happening in this entire period, which makes sense considering its lack of sources and generally murky nature. Historians like to argue about this kind of stuff, and Late Antiquity is a good time to argue about because no one can really establish the truth. For the most part, I’m just the messenger, picking the interpretation that makes the most sense to me about each event and then stitching them together into this narrative. However, the years of 634 to 636 AD are under quite a bit of scrutiny that I feel I need to note. Some new narratives have shifted this timeline to 636 to 638, or claimed that the order of lots of these events is different. It honestly isn’t that important if this timeframe is off two years, but the order of these events is a lot more pertinent to my work here. Some place Khalid being demoted in 636 instead of 634, or the titanic Battle of Yarmouk (we’ll get to it soon, I promise) in 634 instead of 636, and before Khalid’s demotion. Due to confusion of the timeline or a differing source I haven’t been able to confirm, some also say that the Byzantines counterattacked and retook Damascus, after which the Muslims had to take it again. Any of these things could be true, and I am in no way discounting them, but I personally am going to stick to the older narrative which places Khalid’s demotion after the Siege of Damascus (with both events being in 634) and before the Battle of Yarmouk (in 636). While this makes studying the period more confusing, I love that historians are taking a deeper look at it and challenging assumptions. It’s what history is all about! Hopefully, in the future we get more clarity on what played out, but the debate itself is a good sign for the increasing study of Late Antiquity and the Muslim Conquests. On a lighter note, it’s pretty funny that we can’t figure out what year these absolutely seismic events happened. Really just quintessential Late Antiquity.
Following the Capture of Damascus and Khalid’s demotion, the Rashidun army looked to expand further north into Syria and the Levant, with other major cities like Jerusalem, Homs, and Aleppo as their targets. Many accounts place a battle known as the Battle of Fahl (in January 635) as the first battle with Abu Ubayda in command, in which the Muslims defeated a much larger Byzantine army’s attempt to retake Damascus. Fahl is an interesting battle, but again suffers from a lack of reliable sources. The Byzantines reportedly broke a few dams on the Jordan River to make the area the Muslims planned to march through a marsh, which gave the Muslim army a lot of trouble. Still, the Muslims apparently marched through it and defeated the Byzantine army anyway, after which the marsh hindered the Byzantines’ ability to retreat and much of their army was killed there. Numbers in this battle are comical, with some Muslim sources claiming the Byzantine army lost 100,000 men. That number is definitely not true, but in my view this battle probably happened. It would make sense that the Byzantine army outnumbered the Muslims, as it does at almost every battle in this campaign. Most likely, the Rashidun army defeated a Byzantine attack on Damascus, and the part about the Byzantines breaking the dams on the Jordan River seems a bit too specific to be made up. It’s not unreasonable to assume that Khalid also played a large part in this battle as the commander of cavalry and Abu Ubayda’s main advisor.
The Byzantines were not at all fans of that whole “not having Damascus anymore” thing and just couldn’t let go yet. Soon after the Battle of Fahl, Khalid and Abu Ubayda were forced to march back up towards Damascus to counter a Byzantine army sent from Homs to retake the city. The Byzantines were led by another Theodore known as Theodore the Patrician (cool name, sure hope nothing bad happens to him). The two armies met at Marj ar-Rum, west of Damascus. As the battle kicked off, it became evident that Theodore the Patrician had taken part of the army and slipped off in the night to attack Damascus, catching the Muslim army off guard. While Abu Ubayda held off the rest of the Byzantines at Marj ar-Rum, Khalid was sent with a portion of the cavalry to hopefully get back to defend Damascus before Theodore the Patrician could manage to take it. The Byzantines come off as very tricky and competent here, which is a reminder that they were. Khalid ibn-al Walid and Abu Ubayda are guys that are extremely hard to catch off guard, and here the Byzantines managed to do it. There’s a reason the Byzantines owned this crucial region of the world before Islam came around, which in large part stems from the fact they were a military powerhouse bursting at the seams with good generals. The fact they consistently lose to the Muslims isn’t an indictment of them, it just shows how brilliant the Rashidun army (and Khalid ibn-al Walid) was. At Damascus, garrison commander Yazid ibn Abi Sufyan was admirably holding off Theodore’s much larger force, but the garrison was close to breaking. Yazid is another in the line of very skilled Muslim commanders, and interestingly, the older-half brother to the future founder of the Umayyad Caliphate Mu’awiya. Khalid arrived and attacked the Byzantine army in the rear, trapping it between his force and Yazid’s and crushing it. Score number 2,345,634 for the mobility of Khalid’s forces. Theodore the Patrician was killed under the walls of Damascus, supposedly by Khalid in single combat. As a side note, Khalid gets cited as killing way too many people in single combat but I’m leaving it in every time because it’s cool. Back at Marj ar-Rum, Abu Ubayda’s force and the rest of the Byzantine army were locked in generally balanced combat until news of the defeat at Damascus reached the Byzantines, after which they quickly lost morale and retreated.
With Damascus secured, Khalid and Abu Ubayda set their sights on Homs. The Byzantines seem thoroughly depleted for a lot of 635. It’s clear to us now that they were re-gathering their strength and preparing for a massive attack in 636, but for the rest of 635 it’s pretty hard to find any Byzantine armies anywhere near prepared to counter the Rashidun march north. The Muslims swept through northern Syria, taking many cities on the road to Homs without a fight.
This is an important time to note that the population of Syria and Palestine were not particularly hostile to the Muslims. If they were, this entire invasion goes absolutely nowhere. Already outnumbered and in enemy territory, even a mastermind like Khalid ibn-al Walid couldn’t have overcome real grassroots opposition. There are various reasons for this, some concrete facts and some more of my hypotheticals. First, the Muslim policy of jizya, a tax Muslim rulers put on conquered non-Muslim subjects, was a very lenient way to treat religious minorities in this time period. Most other empires were more of the “convert or die” types. Not to mention, if you converted to Islam, you could just stop paying the jizya! A lot of marginalized groups saw opportunity in just accepting Muslim rule and converting to Islam instead of remaining systematically oppressed. Khalid himself plays a part in another reason. As I’ve mentioned in passing before, Khalid was a bit of a proponent of looting and taking some good old spoils of war, much to Caliph Umar’s chagrin. This proved useful when he could bribe tribal or city leaders into supporting his invasion, who could then take those bribes and distribute them to the people whose loyalty they were also buying. Lastly, the Byzantines were pretty oppressive. Not like outlandishly oppressive (for the 7th Century AD), but enough to maybe make you want to take your chances with those other guys. The Sassanids had briefly conquered and held Syria and Palestine during the massive Byzantine-Sasanian war, and the recent memory of rule by another power may have convinced a lot of the population that they would be treated better under non-Byzantine rulers. Tons of groups in the region had a checkered past with the Byzantines and jumped on the chance for a new regime. For example, Jews in Jerusalem were regularly subject to pogroms the Byzantine state did nothing to stop or actively participated in. Simply paying jizya and being left alone looks amazing in comparison. Or, in many more cases, the locals just didn’t put up a fight when the Muslims rolled into town. Another much less deep hypothetical explaining the populace’s lack of opposition to the Muslim invasion is that this region must have been war-weary and completely devastated. It was six years out from being the center of a multi-decade war and had been hit with multiple plagues. These are circumstances that lead people to just try and survive the next disaster, not to put everything on the line for their rulers.
Homs (known as Emesa at the time) was another leading city of the region and a key center of trade. The Siege of Homs was similar to the Siege of Damascus in many ways, but would prove to be a bit more troublesome for the Muslims. The Rashidun army arrived at the gates of Homs in December 635 and would have to face the elements of winter for the duration of the siege. I know what you’re thinking here: It’s Syria, is the winter really that cold? To me, no. To people from the Arabian peninsula? Yes. The Byzantines picked up on this, even to the extent that Emperor Heraclius advised the military governor of Homs to “fight them on every cold day”. Personally, I would also hypothesize that the cold hit Khalid and Abu Ubayda’s army a bit harder because they most likely weren’t carrying a ton of supplies for the winter, which would lend to their incredible mobility. It really is a bit of a shame for the Byzantines that their army was so depleted at this time. Homs was very defensible and quite a good place to make a stand, and it might have been easier than normal to drive off the Rashidun army in the winter cold. I don’t think the Byzantines could have won anything decisive here, however they could have at least kept Homs for a while longer. I’m only going to give scant details on the Siege of Homs because I don’t want to make the classic narrative and military blunder of getting bogged down in a lengthy siege. After using his mobile cavalry to defeat a Byzantine sortie out of the gates, Khalid advised Abu Ubayda to fake a retreat and draw the Byzantine garrison out of the city. This worked like a charm and the Byzantines were encircled and killed nearly to a man. Still, Khalid was reported to say afterward that “these Romans were the bravest [he] had ever met.” The Siege of Homs lasted four months, ending in March 636 and giving Heraclius time to consolidate his forces and plan a massive attack. With the Muslims on the road to Aleppo and looking north to Antioch, the Byzantines were fully woken up to the fact that this was not just a regional threat but an existential one.
Yarmouk
Typically, someone who knows of Khalid ibn-al Walid will first associate his name with the Battle of Yarmouk.
The Battle of Yarmouk is the crown jewel of Khalid ibn-al Walid’s military career, the early Muslim Conquests, and arguably, the entirety of Islamic military history. It is frequently listed as one of the most decisive battles in all world history. It is perhaps the only part of the Muslim Conquests that gets a fair bit of name recognition and study in the West. It’s reasonable to separate the history of the Middle East into “pre-Yarmouk” and “post-Yarmouk”. I personally wouldn’t tend to put that huge of an emphasis on pure military history, but I will admit some truth to this. Smarter people than me go on and on about how purely decisive Yarmouk really was. It’s with these kinds of stakes that Khalid’s actions and achievements take on a different kind of gravity, one that has led to streets all over the Middle East bearing his name. Winning at Yarmouk is the type of achievement that immortalizes a historical figure, but at the same time overshadows all of their other achievements. I hope I have done well enough of a job of laying out why this one battle isn’t all that defines Khalid ibn-al Walid. It’s also important to note that while Yarmouk is the definition of a decisive battle, there were plenty of other circumstances and figures that helped to solidify the position of Islam in Syria, the Levant, and the entire Middle East.
As I alluded to a bit before, the Byzantines’ weak showings in 635 were leading up to something big. In Antioch, Emperor Heraclius was assembling the type of army only a top-tier historical empire can put together. Christian Arabs, Slavs, Avars, Lombards, Franks, Armenians, you name them and they were there. Even Göktürks! Does your army have Göktürks? Yeah, didn’t think so. This army was so large that the Byzantines were able to split it into five forces, which was the whole plan all along. The Byzantines were looking to attack the split Rashidun forces in cities across Syria one by one, holding them in place and preventing them from coming to each other’s aid.
This honestly might have worked, but the Muslims found out the plan very early on when they captured some Byzantine soldiers and got details on the plan from them. How lucky! I’m sure they got that information out of them in a very ethical and not at all violent manner. Knowing the plan, the Muslims faced a crossroads. They could leave their forces separate and try to win every battle against each Byzantine force, outnumbered and most likely being besieged. Or, they could unite all their forces and try to force one decisive battle. This would come at the cost of leaving the territory they had taken in Northern and Central Syria vulnerable and scarcely defended. Khalid was the leading voice in advising to unite all of the Rashidun forces in one place and force the Byzantines to come to battle. One of the clearest points in accounts of this battle is that Khalid was basically calling the shots from start to finish, while Abu Ubayda was more along for the ride. I think it’s possible Abu Ubayda realized how crucial of a moment this was and completely deferred to Khalid’s skill and experience, moving him from the “main adviser” status he held after his demotion to really being the general again. In my opinion, Khalid was still basically the general the whole time, even after his demotion. The language most accounts of the campaign use points to him being the general of all Muslim forces in all but name. Still, accounts of Yarmouk are even firmer in emphasizing that Khalid was making all the decisions, so I’m going to drop Abu Ubayda’s name out of the decision-making for now.
As a little sidebar, Khalid and Abu Ubayda's dynamic is a microcosm of what made the early Rashidun army so successful. While the timeline on Khalid’s demotion is still debated, no matter what their harmonious relationship after it is quite unique. The entirety of military history is littered with defeats driven by the selfish, glory-hunting, petty behavior of commanders. Abu Ubayda so easily could have gotten drunk on power and completely relegated Khalid to the doghouse. At the very least, he could have just claimed more credit for victories in Syria at Khalid’s expense, which would honestly be a pretty reasonable thing for a guy to do in 635 AD. Instead, he recognized that Khalid was a more capable military mind and deferred to him for the good of his men, his religion, and ultimately his reputation. It really does take a certain kind of man to do that, and Abu Ubayda deserves his flowers before he leaves this story. For his part, the fact that Khalid got demoted at the height of his fame and took it completely in stride is just remarkable. Not only did he take it in stride, he actively became a better unifier and leader. It is a remarkable stroke of fortune that the Rashidun Caliphate had two incredibly skilled but humble men leading their armies. I don’t think there’s any chance that two generals of that status in the Byzantine army, for example, would have ever ceded power to each other in a similar way. Even if we take it to an empire that’s a paragon of military discipline and resilience, the original Roman Empire, I don’t think this dynamic could have existed. Honestly, in most other empires, even the prudent and well-run ones, Khalid probably gets executed after he gets demoted. I sometimes wonder what, on a psychological level, made Khalid and Abu Ubayda so able to put their egos aside. The completely uninformed guess I typically come up with is their piety and devotion to the shared ideal of spreading Islam, a goal they presumably saw as much larger than one single person’s glory. It’s interesting to wonder how things may have turned out differently if this power-sharing agreement had collapsed, or if Khalid had abandoned the Rashidun Caliphate after his demotion.
In mid-636 AD, Khalid and the Rashidun army retreated south, trying to link up with all their separate forces, pick good terrain to fight on, and maneuver the main Byzantine force onto that terrain at the same time. Sounds like a pretty tough task for an army that isn’t incredibly mobile, so it’s a good thing someone made sure that was a strength. The Byzantines weren’t looking to get into a decisive battle but did have to keep an eye on the growing Muslim army, drawing their main force (under an Armenian general named Vahan) south as well. Moving south, the Byzantines ran into the problem that most settlements were still in Muslim hands, and sieges weren’t going to do much good if the main Rashidun army was still out there. As the Rahsidun forces linked up and retreated into rocky terrain near the modern Syria-Jordan border, they were also scouting advantageous battlefields. It’s a common thread in most of Khalid’s battles that he tends to pick the battlefield and use natural elements in his favor, and nowhere does this shine through more than Yarmouk. Khalid lived a few steps ahead of every enemy he ever faced. He spent months baiting a trap and luring Vahan into it.
Quite a bit of movement, delaying, and posturing were done in these few months before the battle actually started in August 636. These tactics aren’t incredibly well-sourced, and this battle is incredibly complicated, so there are a few simple things to keep in mind. First, the terrain: this battle was on a plain surrounded by a lot of impassable natural features, especially very steep ravines along the Yarmouk River. There are not a lot of exit routes to get off this plain safely, especially if thousands of people are trying to get off of it at the same time while thousands of other people simultaneously try to kill all of you. There’s one hill on this plain. It’s not very big, but the Muslims have control of it, giving them a better view of the battlefield. The plain is pretty large, but constricted enough by the natural features around it that if your army is huge, it’ll impact their movement a bit. If your army is smaller and very mobile, this plain is far more advantageous for it. Next, the troop numbers: No one agrees on exact numbers for Yarmouk, but the Byzantine army was larger. Some contemporary Arab sources, who were very prone to exaggeration or just outright lying, place the Byzantine army at as much as 200,000 men and the Muslim army at as low as 15,000. Some historians who like to say controversial things for fun place the armies at equal size. The Byzantines had a larger army for sure, but the real numbers aren’t something we’re ever going to know for sure. The Rashidun army has more precise estimates which typically even out to around 25,000 men, so we can call it that. Estimates for the Byzantines are the tricky ones, and there’s only one Byzantine source, a monk named Theophanes. He put the Byzantine army at 130,000 men, and he had no interest in inflating Byzantine numbers because they lost. No disrespect to Theophanes, who’s an incredibly important chronicler of Byzantine history in the 7th and 8th centuries, but I don’t think they had 130,000 men there. Modern estimates definitely skew lower, and I’d probably lean towards a conservative estimate that the Byzantines had somewhere between 50,000 and 80,000 men, around double to triple the size of the Rashidun army. Lastly: Remember how the Byzantine army is made up of an assortment of different groups? A lot of them didn’t have much in common, or had their own commanders they liked listening to more than Vahan. There are a lot of rivalries, different languages being spoken, and general tensions in the Byzantine army, from the lowest of foot soldiers to the highest echelons of command. The Rashidun army has no such problems. It’s a rock-solid unit full of people who have fought together for years and who are all wholeheartedly loyal to Khalid ibn-al Walid. Adding to the morale factor, Khalid was constantly being sent small groups of reinforcements from the Persian front by Caliph Umar, making the Byzantines feel pressed to attack sooner rather than later. If they had the high ground, they probably would have seen that these reinforcements were far too few to make the troop numbers anywhere near even.
Traditional accounts of the Battle of Yarmouk say it lasted six days. The battle has a general theme, but a lot of conflicting accounts and gaps in information obscure our look into it. Over the first four days, the Byzantines pressed their numerical advantage, especially on the flanks of each formation. The Byzantines had organized their army so it stretched across the entire plain, and the Muslims had reacted by doing the same. However, since the Byzantine army was so much larger, the Muslims had to leave larger gaps in their formation. Khalid could have covered these gaps with some of his cavalry, but he instead kept it in a mobile guard that stuck with him behind the troop formation. By doing this, Khalid could take the mobile guard to whichever flank needed more help at the time, and once the situation was stabilized he could swing it around to another area in danger of collapse. By all accounts, the mobile guard saved the Rashidun army at least a few times over the first four days of the battle. At points, one flank of the Rashidun army would get pushed all the way back to their camp before Khalid could arrive and lead a counterattack. While the Byzantine attacks were costly to the Muslims, the Muslim counterattacks were even more costly to the Byzantines. When the Muslims counterattacked, the Byzantine force on that flank would be getting hit both by the Muslim infantry in their front and Khalid’s cavalry in their side. Vahan kept ordering these attacks, desperately seeking a breakthrough that seemed so close, and you can’t really blame him as many times it was. While the Muslims were taking less casualties, it clearly wasn’t smooth sailing. On the fourth day of the battle, Byzantine horse archers hit them with so many arrows it became known as the “Day of the Lost Eyes.” If there’s a “Day of the Lost Eyes”, you’re fighting in August on a Syrian plain, the cavalry keeps having to run around and save the whole army, and the battle lasts six days, I think it’s safe to say soldiers in the Rashidun army weren’t having a great time at Yarmouk.
Fortunately for the Muslims, it was even less fun to be a part of the Byzantine army at Yarmouk. In most cases, the overall pattern and long length of the battle would be a good thing for the larger army, who could just slowly grind down the smaller one through sheer numbers. It wasn’t here. The morale factor weighed more and more each day on the Byzantine army, made up of many groups of people who simply didn’t want to be there. Vahan’s strategy had been the exact same thing for four straight days, and troops who already didn’t really respect him were getting demoralized by its repetition and seeming futility. With this in mind, Vahan made a critical mistake. On the morning of the fifth day of the battle, he sent emissaries to negotiate a truce. Khalid smelled blood in the water. Even if the situation had been worse for the Muslims, there isn’t a chance Khalid would have ever accepted. This was the decisive battle he had wanted, he was in the situation he had been trying to create for almost a year. Khalid agreed to a day for both armies to rest but nothing more. Except now that he knew the Byzantines were weak, he proceeded to make brilliant military decisions instead of resting. Previously, Khalid had left some escape routes from the Yarmouk plain open in case his army needed to use them. Now, during the night, he sent small groups of cavalry to capture and block them.
When dawn broke on the sixth day of the battle, the two armies lined up in similar formations with markedly different intentions. The Muslims came with a plan to take the initiative and deliver a killing blow, while the Byzantines came in with, well, we don’t know. It may have been the same plan as the first five days or it may have been something completely different, but we don’t know because they never had the chance to enact it. As the two armies engaged again, Khalid took nearly all his cavalry and swung it around the left flank of the Byzantine army, crashing it into both the cavalry and infantry stationed there. Steadily, this began to push the Byzantine left flank back into their center, allowing more of the Muslim cavalry to pour around their flank. It was at this point that the Byzantines needed their remaining cavalry to stabilize the situation, in a similar way to how Khalid’s had when the Rashidun army was in trouble. It was the most critical point in the battle. With the fate of Syria hanging in the balance, Vahan couldn’t get his cavalry together. Vahan wasn’t a bad commander, but he’s getting hit with one of Khalid’s most daring moves ever and he simply didn’t measure up to the moment. Khalid was banking everything on his cavalry’s speed and the Byzantine cavalry’s relative slowness. The Muslim cavalry sprinted behind the Byzantine lines with a desperate fury, mowing down anyone in their path. The Byzantine cavalry was trying to form up and charge to meet the Muslims, but they were split up on different parts of the front with different commanders who spoke different languages, seconds and minutes ticking away as they tried to come together in one place and one formation. They were still trying to mass together as Khalid’s cavalry bore down on them with alarming speed, a sight that must have felt like watching a tornado move closer and closer. It was now or never to start a charge and intercept the Muslim cavalry. The Byzantines were perhaps a minute too late. Khalid and his men slammed into them at full speed while they were flat-footed, disorganized, and confused. The Byzantine cavalry that wasn’t immediately killed broke and ran. After pursuing the Byzantine cavalry off the field, Khalid swung his cavalry into the rear of the Byzantine infantry at the point where the left flank was collapsing into the center. A general retreat of the Byzantine infantry began as their commanders tried to keep them in good order and escape to the West.
To the West laid a 700-foot-tall ravine with exactly one bridge over it. The Byzantines desperately fought their way back towards the bridge, their main chance of an escape from the Yarmouk plain and potential survival. Straining to maintain formation and avoid a rout, the thought of the bridge must have been the only thing keeping each Byzantine soldier from indulging the overwhelming human instinct to break and run.
One can only imagine the sheer, overwhelming terror that struck the first Byzantines who reached the bridge and found it blocked by Muslim cavalry. The news must have spread through the packed ranks of tens of thousands like a wildfire, burning any last semblances of morale or composure. They were surrounded on all sides. There was no escape. Chaos ensued.
At that moment, perhaps every surviving Byzantine commander simultaneously realized why Khalid ibn-al Walid had spent the entire day trying to push them to the West.
The ending of Yarmouk was like that of so many other battles Khalid had fought to this point: an enormous slaughter of the enemy. Byzantine men fell or willingly jumped into the ravine, died trying to force the bridge, or simply were cut down trying to run. The Muslims took no prisoners. The Byzantine cavalry that had fled the field earlier on were eventually chased down and killed, Vahan among them.
The Byzantines had played their best card and lost. With the Caliphate’s overwhelming victory at Yarmouk, the entire regions of Syria and the Levant were now firmly under Muslim control or soon to be. The Byzantines would never again have the men or resources to attempt to take them back.
Khalid’s tactics, overall strategy, organization, and quick thinking at Yarmouk rank the battle as his greatest military achievement and one of the most impressive victories in all of military history. In terms of a famous victory, this battle had it all: an overwhelming troop disparity, mind games, ingenuity, huge risks, a formidable enemy, and the perfect execution of an incredibly well thought-out plan. It even had Göktürks.
Yarmouk is inarguably a battle of titanic impact, but it suffers from the same gaps in information that the Muslim Conquests and Late Antiquity in general suffer from. This dichotomy of extreme historical significance and a lack of a place in historical memory is what inspired me to write this piece. Can you think of any time, where so much hung in the balance, that we have so narrow of a look into? Can you imagine if, I don’t know, we only had three accounts of the American Civil War? Can you imagine if people were too busy trying not to die to write about the Renaissance? Can you imagine if we didn’t know anything about Napoleon’s life until he turned 30, and then only had scant details of it after? What if we could only guess what life was like in the Roman Empire, and therefore few people even knew it existed? Late Antiquity is an enigma full of contradictions and paradoxes, with so little to analyze and so much to imagine.
The Final Years
When he knew all was lost, Emperor Heraclius reflected on the Byzantines’ crushing defeat and blamed it on his own sins. As Antioch faced imminent conquest, he boarded a ship to Constantinople and bade farewell to Syria, quoted in a few sources as: “Farewell, a long farewell to Syria, my fair province. Thou art an infidel’s (enemy’s) now. Peace be with you, O Syria — what a beautiful land you will be for the enemy’s hands.” Emperor Heraclius isn’t a character that I’ve featured heavily here, but he is a remarkable man and one of the faces of Late Antiquity. He took over the Byzantine Empire in the thick of its war with the Sassanids, with various provinces lost and the empire on the brink of collapse. Over a grueling two decades, he fought off disaster on multiple fronts and even a siege of Constantinople itself. Eventually, he turned the tide and defeated the Sassanids at huge cost, preserving his empire’s survival and entering him into legend. Emperor Heraclius almost certainly looked back in his final days and wished he had died in 631 AD instead of 641 AD, before Khalid ibn-al Walid swept through his lands. When the Muslims invaded he was a tired and frail old man, and he probably could have handled the situation better. Still, I don’t think it’s fair to blame Heraclius for losing Syria; he wisely put most decisions in the hands of his generals and faced an incredibly fierce enemy. Yet once it was over, Heraclius must have known it was the beginning of the end for the empire he had dedicated his whole life to saving. Syria, Egypt, Palestine, and other provinces that had been lost in his last years would never return to the Byzantine realm. He did an admirable job in fortifying Anatolia and setting the Byzantines up to defend against future incursions, but successive Muslim states would slowly chip away at the doomed empire until its fall eight centuries later. There’s something deeply moving about Heraclius desperately searching for answers as to why he had achieved so much just to see it all fall apart in his final years, too old and sick to be the leader he had been when the Persians were at the gates. Having lost decades of his life and countless friends in defense of his lands, one can only imagine the emotions Heraclius felt as his life’s work dissolved into the sands of Syria, the realization washing over him that it was all for naught. As he watched Antioch disappear beyond the horizon for the final time, and all that remained ahead of him were the dark Mediterranean waters, the only explanation Heraclius could find was that God had forsaken him.
Sometimes, history deals you an unwinnable hand. There are few hands more unwinnable than simply being born in Late Antiquity. You can do everything right and your reward might be to run into Khalid ibn-al Walid.
It all gets somewhat quiet for Khalid after Yarmouk. Sources are even more scant on the details than usual, but we’re aware he was still in Syria essentially doing cleanup operations for a bit. Yarmouk made the Rashidun conquest of Syria and the Levant inevitable, but it didn’t expel every Byzantine garrison from the area. While Khalid’s services would still be needed, they seem to be markedly less important after 636. Yarmouk is the climax of his story, and naturally it comes near the end.
It’s kind of wild to have “taking Jerusalem for Islam” be a footnote of your career, but Khalid managed it. At the end of 636, the now-ascendant Rashidun army surrounded the Holy City and conquered it in four months after a mostly bloodless siege. The Christian Patriarch wouldn’t personally surrender to Khalid, and he demanded that Caliph Umar come all the way from Mecca to accept his surrender. Umar did so. Centuries of resentment and war, whole ideologies, and extremely visible present-day effects all came out of the Rashidun Caliphate conquering Jerusalem. I’d argue it isn’t even in the top 10 of Khalid’s most impressive victories.
A little callback to why this was at all possible: One of Umar’s first actions after taking control of Jerusalem was to allow Jews to live inside the city again as long as they paid jizya. These kinds of deals were being worked out on every front of the Muslim Conquests for years on end, and Khalid was one of the main people working them out. A lot of that looting Khalid has been in trouble for was done to distribute it to powerful local figures in exchange for their passive acceptance of Muslim rule. A happier population means an easier conquest and much easier rule. Maybe this prudent, astute manner of ruling will lead to a Golden Age a few centuries later, who’s to say?
Aleppo, Antioch, and all of the remaining great cities of Syria fell to Khalid in 637. This seems like a lot to brush over, but there isn’t really much I can say about it, unfortunately. The sources for each battle just aren’t there or they don’t provide the detail necessary to convey what actually happened. At this point, it’s all getting quite routine for Khalid. You don’t really need to have ironclad sourcing to know that he’s doing crazy stuff with the cavalry and bringing ruin to the Byzantines. I’ve also chosen to brush over these because of the deep sense of inevitability of them. There’s very little drama after Yarmouk, it’s all kind of a foregone conclusion. If there was a less skilled commander in place than Khalid, they still would have managed to take Jerusalem or Antioch. The Byzantines were simply cooked. Of course, they were only cooked because of Khalid. It’s interesting how the incredible significance of his most famous victories actually lessens the significance of his victories after them.
In 638, Khalid was very spottily recorded to have undertaken an expedition north of Antioch into the Taurus mountains. When he returned, his soldiers were absolutely loaded with wealth. Muslim historians write about the amount of spoils of war with a palpable sense of awe. At this, Caliph Umar finally decided he had enough. Demotion wouldn’t be enough this time. Khalid was formally dismissed from command that year and would never fight another battle. Not one senior Muslim figure is recorded to have objected to this decision or stood up for Khalid, not even Abu Ubayda. I get that if you’re in a Caliphate, it’s pretty hard to disagree with the Caliph. Still, it all just feels terribly unceremonious.
Khalid’s dismissal and the lack of backlash to it comes down to a few things, many of which I’ve already mentioned in passing. First, Khalid had done his job and his military skill was no longer urgently needed. Syria and the Levant had been fully conquered, Umar was delaying the Caliphate’s expansion into Egypt and North Africa, and different generals were already building off his successes in Persia. The Taurus Mountains formed a natural barrier to expansion into Anatolia, saving the Byzantine Empire from full conquest in the upcoming centuries. Khalid was also becoming a pretty old man in a premodern sense. He’s likely coming up on or past fifty, and there are young, ambitious, well-connected commanders waiting for their turn. Second, it seems like everyone knew Caliph Umar was looking for an excuse to dismiss Khalid, so it didn’t really come as a shock. Khalid’s fame, achievements, and riches had provided him with devoted followers that threatened Caliph Umar’s position as the most powerful man in the Rashidun Caliphate. A lot of Caliph Umar’s reasoning stems from the idea that Khalid was beginning to be venerated as a bit of a divine figure, which more devout Muslims really didn’t like as they figured all worship should be going toward Allah. It’s a point that makes a lot of sense, especially considering the context of the Rashidun Caliphate being an extremely pious theocracy. In this environment Khalid wasn’t considered a very pious figure. He comes off as pious in quotes attributed to him, and his achievements undoubtedly spread Islam, but as a powerful figure in a Caliphate that was the bare minimum of piety. In the eyes of a lot of clerics many of his actions bordered on heresy. Khalid not only had detractors in the religious establishment, he also had a lot of other powerful enemies. In a land where tribal loyalties ran deep, many people simply didn’t like him for being Makhzum. His fairly brutal conduct in the Ridda Wars hadn’t won him much favor among influential people on the losing end of it. In fact, Khalid is still reviled by the entire Shia Muslim tradition for killing Malik ibn Nuwayra. Around 15 percent of Muslims worldwide are Shia, and that number was a lot higher at many points in Islamic history.
Thankfully, Khalid’s achievements and fame were seismic enough that he wasn’t written out of history entirely, although many did try. The combination of these attempts to remove Khalid from history and the lack of sources covering Late Antiquity do damage to Khalid’s legacy, but thankfully they didn’t destroy it. He’s not as famous now as he could have been, but at the very least he’s still a famous figure in the Islamic World. It seems Muslim writers realized their predecessors’ mistakes in the centuries after Khalid’s death, because writers from the 9th century onwards are quite a bit more positive about him and much more generous in the credit they give to him. In fact, it’s possible that these writers are the only reason Khalid’s image was rehabilitated and most Muslims consider him a hero today. I will admit some of these writers go a bit far in how they portray Khalid and the Caliphate’s treatment of him. Some claim that Caliph Umar felt deep, piercing regret over how he treated Khalid years after the fact. Personally, I think Caliph Umar slept pretty soundly after dismissing Khalid. Even though I’ll admit that this is a Khalid ibn-al Walid puff piece, some of these sources from the height of the Islamic Golden Age really do treat him as a god. Funnily enough, that’s exactly what all those guys high up in the Rashidun Caliphate were worried about in the first place. The way history is written reflects contemporary beliefs and attitudes, and people’s perceptions of Khalid warmed over the centuries.
When someone stops doing things that alter the course of history, it’s pretty tough to keep track of them in Late Antiquity. No one knows anything about Khalid’s final few years. As a famous and rich figure, I would think he was generally treated well after his dismissal but we don’t really know. He died in 642 but no one knows where or from what. He was buried in Homs, and there’s a prominent mosque in the city that bears his name and contains his tomb. This at least tells me that he was given a lot of honor by the authorities when he died, but it’s impossible to confirm. Again, it all just feels too unceremonious for a man so important to their cause. In a deeply saddening turn of events, the Khalid ibn-al Walid mosque was heavily damaged in the Syrian Civil War after being shelled in the battle for Homs. A lot of the places Khalid and the Rashidun Caliphate conquered have had an incredibly rough past few decades, and really, past few centuries. Modern perceptions of these areas can very easily overshadow their incredible histories. For centuries before Khalid and centuries after him, Syria and Iraq were among the most prized lands in the world.
The Match Made in Arabia
There’s a famous quote: “There are decades where nothing happens; and there are weeks where decades happen.” I think Khalid’s life was a series of decades where centuries happened. The historical magnitude of the events Khalid ibn-al Walid lived through and participated in is remarkable.
With that being said, whether it’s Khalid or a universally-known figure like Julius Caesar or Genghis Khan, people can quickly fade from historical memory if we don’t actively study them and tell their stories. I’ve already written at length about the various reasons Khalid dropped out of historical memory for a bit. To an extent, this is what has happened with Late Antiquity as a whole. There’s a reason the term “Dark Ages” was used until recent years, and there’s leagues of ground Late Antiquity needs to cover in order to be a historical period we scrutinize to the level of Classical Antiquity, for example. Scholarship of Late Antiquity has taken massive leaps in the past decade or so, and lots of what was previously left alone is being written about, called into question, and discussed at a high level. For the casual history fan, the problem is that this discussion of Late Antiquity is taking place at a bit too high of a level. New historical conclusions will eventually disseminate to the public as they always do, but for now the resurgence in study of Late Antiquity is largely confined to some academic circles that I am definitely not a part of. Late Antiquity’s lack of sourcing, perception of being a “Dark Age”, and complexity make it hard to access. How can it become more accessible and studiable to people outside of history professors?
One way, at least I believe, is to look at the lives of people like Khalid ibn-al Walid and through them access the events and the world that they were part of. “Great Man History” like this isn’t endorsed in history programs, and for the most part it isn’t the right way to draw deep conclusions. However, in my eyes, there’s the odd situation where indulging in it is useful. I think this is one of those situations. Khalid is one of the only people written about enough to analyze in Late Antiquity, and his story is one way I’ve been able to ground myself in the study of the period. Khalid’s story tells you about the inception of Islam, the challenges it faced in its first years, and the unbelievable improbability of it becoming the global religion it is today. He brings you into quite a bit of contact with the Byzantine Empire and Sassanid Persia, megastates that defined Late Antiquity. He shows you many of the drastic changes that occurred during his lifetime which are crucial in shaping the world we live in today. In his story we see the ambitions, beliefs, and movements, but also the destruction, chaos, and misery that defined Late Antiquity. Along with all we are shown, we’re also aware of what’s missing. Massive details, important context, and other wide swathes of information are missing from accounts of Khalid ibn-al Walid as well as accounts of basically everyone and everything else in Late Antiquity. He is a perfect fit of a historical figure to a historical period. Khalid ibn-al Walid’s story not only hits on all the key points of Late Antiquity, it does so in a way that encourages you to dive deeper into the period. His life is a beacon on the landscape of the “Dark Ages”, and I hope that light can eventually make its way to other understudied figures, events, and societies of the period.
Apart from all the historiographical hodgepodge, Khalid ibn-al Walid’s story is also just a good story on a base level. It’s triumphant and sad and morally gray and wild. Absolutely insane things happen in Khalid ibn-al Walid’s life and you should be aware of them. His story provides incredible twists, turns, and drama. In the end, if you like studying history it’s because it captivates you. It’s this childlike curiosity, piecing together the unknown through infinite stories and trying to put yourself in places and times you can never go. There’s so much to piece together in both Khalid’s life and in Late Antiquity, so much to think about but so much that drives you to know more.
