Charles Cornwallis: The Man Who Lost the American Colonies

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You probably know the old saying: some are born to greatness while others have greatness thrust upon them. During the years we’ve been making these videos, we’ve covered hundreds of men and women who fall into both categories. We’ve even covered plenty of people for whom greatness meant doing something consequential but awful—your Stalins and your Maos.

What about those whose destiny isn’t to be anywhere close to greatness? Those who were born to or had mediocrity thrust upon them, only for that mediocrity to hold history? For Charles Cornwallis, this wasn’t an abstract question; it was his very life. Born into the English upper classes, Cornwallis had the misfortune of embarking on a military career just as England’s American colonies exploded in revolt. Promoted above his head and shipped out to fight, he wound up being the Redcoats’ commander at Yorktown, where surrender ended the Revolutionary War and ensured Britain forever lost her 13 colonies.

In today’s video, we’re examining the life of a mostly decent but ultimately ineffective man—a man who somehow still managed to change the world.

When Charles Cornwallis was born on December 31, 1738, it was into a family that was spectacularly well-connected. His grandfather was the brother-in-law of the great Robert Walpole, while his father would soon be made both an Earl and a Viscount. The family also stood in good grace with the monarchy. Despite likely having Cornish Irish roots, the Cornwallises were famously loyal to the British throne—a trait that Charles would inherit and one that would land him in a lot of trouble.

For now, though, young Charles enjoyed a typical childhood among the English upper classes, attending Eton with future dukes and learning about military glory. The boy evidently liked what he learned; as a teenager, his fascination with war was intense, even by the standards of the time. Despite having a body shape we might charitably call unremarkable and suffering skewed vision from a sporting injury, Cornwallis was determined to one day fight for king and country.

That day came sooner than he expected. In August 1756, just as Charles was enrolling at Cambridge, Frederick the Great of Prussia invaded Saxony. For the past two years, America’s British and French colonists had been fighting one another in the French and Indian War. Frederick the Great’s attack on a French ally in Europe was the opening of a whole new theater of combat. With Britain now allied with Prussia in this increasingly global conflict, Charles decided to abandon his studies and become the soldier he had always dreamed of being.

From 1757 to 1761, Charles Cornwallis toured Europe with the Prussian army, fighting in some of the biggest battles of his era. He clearly made an impression; by the end, he was promoted to lieutenant colonel. Even before the fighting finished, he was able to translate his military glory into a seat in Britain’s House of Commons. Not that it lasted for very long. In June 1762, his father died, and Charles inherited his title. A year later, as the Seven Years’ War finally drew to a close, he took his father’s seat in the House of Lords.

Long a byword for stuffy conservatism, the Lords nonetheless had a handful of liberal-ish members even in Cornwallis’s day, known as the Rockinghamites after their leader, Lord Rockingham. They managed to recruit the New World just as politics got very interesting. Being on the winning side of the Seven Years’ War had been great for Britain’s standing, but it had been terrible for its finances. Since expelling the French from America primarily benefited the 13 colonies, it was decided the colonists could refill the king’s coffers. And so we come to the infamous Stamp Act—taxes on all paper and printed materials in the colonies.

The Stamp Act was kind of like George III personally slapping every American in the face with a bit of a frilly glove. It was also the stupidest thing that Cornwallis had ever heard of. In the Lords, Cornwallis became a passionate enemy of the Stamp Act, deeming it unfair to the Americans. When Lord Rockingham became Prime Minister and repealed the act, Cornwallis was one of those who cheered the loudest. But Rockingham also passed the Declaratory Act, which basically said to the Americans, “Okay, fine, we won’t tax you now, but we absolutely have the right to.”

Only five peers voted against this new law, among them Charles Cornwallis. Yet while he cared about all this, politics wasn’t Cornwallis’s lifeblood; it wasn’t what made him get out of bed in the morning. In 1768, he was ready to retire from the Lords and settle down with his new wife, Jemima. This would be the happiest period of his life. Jemima was the daughter of a soldier far below Cornwallis’s class, but he married her for love, and the two soon settled into a blissful and uneventful domestic life. As the years passed and the two became parents, it’s just about possible to see how things could have turned out differently—a world in which Charles Cornwallis was only ever an obscure, happy nobody.

But unfortunately, Charles did not live in that world. In this world, he was destined to not be forgotten but to go down in infamy. While Charles Cornwallis was happily slipping into retirement, the British government was happily pouring gasoline onto the Stamp Act dumpster fire. Just a year after the Declaratory Act, the Townshend Acts slapped duties on British exports to the colonies. This led to a boycott of British goods, which in turn led to British soldiers being sent to Boston, culminating in the Boston Massacre when soldiers fired into a mob, killing five.

In the wake of this, Parliament repealed the Townshend Act and decided to stop levying unfair taxes on the Americans once and for all—not really. Instead, you had the Tea Act of 1773, which led to the Boston Tea Party and then the Intolerable Acts, by which point the thirteen colonies had basically become a powder keg. Finally, on April 18, 1775, British troops lit the match by marching out to seize weapons held in Concord. En route, they bumped into a waiting militia in Lexington. Someone fired a shot, and the rest is history.

Okay, so now we’ve recapped third-grade American history class; it’s time to check back in on Cornwallis. Despite having been Parliament’s guy most likely to make heart signs in America, the moment the revolution broke out, Cornwallis defaulted back to his king and country mode. Although his wife begged him not to, he volunteered to fight and was promoted to major general, shipped out on February 12, 1776. On May 3, his ship made landfall in North Carolina.

At this point in the story, Cornwallis met his lifelong nemesis, Sir Henry Clinton—the man who would eventually head all the British forces in the colonies. Clinton was a sensitive, moody, envious, incompetent, entitled screw-up of a commander. From almost the moment they met, Clinton and Cornwallis regarded one another with mutual loathing—a loathing that would eventually deteriorate into outright hostility. But in those early days, the British could still pretend that this was just teething problems, as Cornwallis was sent north to reinforce William Howe in New York.

It even looked like the war might be over before it properly began. That summer, Cornwallis commanded the reserve troops in the Battle of Long Island, a cataclysmic defeat that saw George Washington lose New York City to the British. Although William Howe let the American general slip through his fingers, Cornwallis was certain they’d catch him soon. Unfortunately, it quickly became clear that slipping through fingers was something Washington was rather good at.

The next six months of Cornwallis’s life reads like the synopsis for a rejected Road Runner cartoon in which Wile E. Coyote briefly commands a major part of the British army. There was the Battle of Fort Lee in November, which ended with Cornwallis forced to chase the slippery Washington all over the state. Then there was Cornwallis’s inexplicable decision to let Washington go after finally catching up with him—a moment that may have cost the British the war.

Finally, that was what happened at Trenton on January 2, 1777. After marching a whole day to catch Washington, Cornwallis allowed his men to sleep rather than immediately fight. Stupidly, he forgot to post lookout, so Washington simply waited until nightfall and then slipped away again, leaving Cornwallis’s reputation to plunge, Wile E. Coyote-like, into a bottomless pit. When Clinton got the news of this blunder, he remarked it was “the most consummate ignorance I ever heard of in any officer above a corporal.”

As we’ll soon see, though, Clinton was himself no slouch at ignorance. Cornwallis did at least have one thing going for him: throughout all the wars he’d ever been involved with, the Earl would do his best to make sure his men were well-fed, paid on time, and not made to suffer. It’s here that we see one of the sad contradictions of Cornwallis’s life. Up to a certain point, he was a competent man with a humane streak—rare for his class. Had he been a bit less privileged, he would have made a fine logistics commander or lower-ranking officer. But this was the 18th century, an era in British history when background was valued above ability.

Poor old Charles Cornwallis was going to keep failing upwards until it killed him. And as you know, perhaps all Cornwallis might have failed a little less if he had quick and easy access to the greatest wisdom of his time. He didn’t have Blinkist because it was the 18th century, and books were still being written with feathers back then. But you have no excuse. Look, if you’re like me, you’ve got plans to read lots of new books this year because you want to add to that sweet bank of knowledge that you keep in your big brain. Unfortunately, reading takes time, energy, and attention—all things that are often lacking. Fortunately, though, I have Blinkist. This is an app that offers easily digestible 15-minute summaries of the best non-fiction books. There are more than 3,000 of them you can either read or listen to. Personally, I listen about 90% of the time, just like a podcast. It’s easier to fit into my day that way while doing mindless things like going to work or cleaning the kitchen or folding the laundry.

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Now, let’s get back to Cornwallis. While the image is of Cornwallis as some kind of doofus cartoon coyote, we don’t want you to go away thinking he was completely useless. The key takeaway is that he was average—an average guy in a position that required someone well above average. But even the mediocre have occasional moments of greatness. Cornwallis’s came at the Battle of Brandywine. Brandywine is notorious today as Washington’s biggest screw-up, but from the British perspective, it was a triumph. Taking place on September 11, 1777, it saw William Howe and Cornwallis launch a dual attack on Washington’s troops under the cover of fog. Assuming Howe’s division was the entire British force, Washington left his right flank open, only for Cornwallis to come crashing into it.

The Continental Army suffered over 1,100 casualties compared to just 600 for the British. Although Washington again slipped away, he lost all of his artillery pieces, and Philadelphia now lay wide open for Cornwallis. The sneak attack was a huge personal victory; he was even allowed time off that Christmas to go home and see his wife. We can only hope he enjoyed it because that Christmas would be the last normal one that Charles ever spent with his family. The following winter, Jemima was taken ill; she died on February 16, 1779. Thanks to emergency leave, Cornwallis made it home just in time to see her, but with the war still raging, he had no time to mourn. Instead, he had to pack back up and return to America, his domestic life in England no longer something to look forward to—just a happy memory of better times.

Back in the colonies, the war was moving inexorably against the British. The French and Spanish were now involved, the Americans had refused to surrender after Philadelphia fell, and Henry Clinton was now overall British commander—with predictably poor results. So Cornwallis decided to change tactics. In May 1780, he headed into South Carolina at the head of a vast fighting force, determined to open a new front. Charleston fell quickly, as did other key strategic points. Before long, Cornwallis had effectively taken control of the entire state. When General Gates attempted to retake the town of Camden for the Continentals, Cornwallis even managed to win another great victory, killing or capturing nearly 2,000 Americans while losing only 300 of his own men.

Come fall of 1780, Cornwallis was secure in South Carolina. Had it been his dream to rule the state as a warlord, he would have been pretty happy. But of course, that hadn’t been Cornwallis’s goal. He wanted to take North Carolina too, then march into Virginia and link up with Clinton’s army. Like so many dreams, it would prove to be beyond Charles Cornwallis’s reach. North Carolina was not South Carolina. The mini civil war between patriots and loyalists was more bitter here, and the terrain was less friendly. In January 1781, the Battle of Cowpens saw many of Cornwallis’s best soldiers killed or captured. Two months later, Cornwallis squared off against Nathaniel Greene at the Battle of Guilford Courthouse and managed to rack up a technical victory that cost so many of his remaining soldiers that you might as well call it a defeat.

By now, the great victory at Brandywine must have seemed like a long time ago. Even the Battle of Camden was three-quarters of a year past. Still, Cornwallis gamely pushed on, marching up into Virginia despite North Carolina not yet being pacified. In May of 1781, his exhausted men finally reached the James River, at which point they received a fateful order. A message from Clinton came demanding Cornwallis establish a fortified base at either Williamsburg or Yorktown. As far as Cornwallis was concerned, this was like Clinton asking him to choose between a kick in the nuts and a rectally inserted cactus. Neither was particularly pleasant to contemplate, but orders were orders. With what we can only imagine was a pained sigh, the Earl chose the kick in the nuts that was Yorktown.

Little did poor Charles Cornwallis know it, but he’d soon be wishing he’d chosen the prickly, comforting cactus in Williamsburg instead. The moment Cornwallis settled in Yorktown, the Revolutionary War was basically over. The French and most of the Americans immediately realized the British were sitting ducks. Although Washington initially ignored it as a sideshow, he eventually realized its significance. The only person who never figured it out was Henry Clinton. Ensconced in New York, Clinton was certain Washington was going to attack him—so certain that when he received a pathetic plea from Cornwallis begging for more troops, he ignored it. But Washington was already making plans to head south for the final battle.

On September 28, the combined American and French forces began their assault on Yorktown. As the siege trenches were dug and the artillery began, Cornwallis sat tight, barely bothering to give orders. It’s possible he thought Clinton was coming to rescue him, or he may have just realized how hopeless his position was. On October 14, the first assault began. In his last act of competence, Cornwallis began ferrying his men to safety across the James River. He got a thousand of them over before a storm blew up and ended it. Impossible escape cut off, there was nothing to do but wait for the end. At 11 a.m. on October 19, 1781, the British surrendered Yorktown. It was a frankly pathetic end. As the Redcoats marched out, they acknowledged the French battalions but ignored the American troops. Cornwallis himself refused to meet Washington for the formal surrender, instead sending an assistant. It was a cheap last-minute snub, but it didn’t change the fact that the man he was snubbing had just handed Cornwallis his rear end.

Yorktown ended the Revolutionary War. Thanks to a combination of Clinton’s poor leadership and Cornwallis’s painfully mediocre performance, the British were knocked out of the fight. Of course, the wind had been blowing in that direction for a very long time. It’s not like Cornwallis was single-handedly responsible for the British losing the war, but he also didn’t do much to help them win. Had he been just a bit more talented, a bit more daring, a bit more well—anything really—well, over six years of fighting could have really added up. A few more Brandys here, another Camden there, and the history of America might look very different.

Despite his major role in losing the 13 colonies, though, Cornwallis didn’t return to Britain under a cloud of shame. The view in London was that he was a good loyal soldier and, more importantly, a gentleman—one who’d been put in an impossible position. All of which is why, within seven months of the disaster at Yorktown, Charles Cornwallis was offered military control of British India. I know, right? This guy’s literally just proven himself to be super ineffective at this, and here’s the British establishment being all like, “Want to try something even bigger?” I mean, why not? At least Cornwallis himself had the brains to say no—something he kept saying for four whole years.

You can’t have people failing upwards without the complicity of everyone else, though. In February of 1786, after years of cajoling by Prime Minister Pitt the Younger, Cornwallis finally agreed. He had only one request: still smarting about Clinton’s dumb orders, Cornwallis demanded he be given total control of the subcontinent, and Pitt agreed. So rather than retiring into obscurity, Cornwallis sailed off for India. Would it go any better than America did? Well, what do you think?

The India Charles Cornwallis arrived in was undergoing a seismic change in its relationship with Britain. Until recently, the East India Company had almost free reign over its territories. It was in