in: Character, Knowledge of Men, Podcast

• Last updated: September 29, 2021

Podcast #223: George Washington, Benedict Arnold, and Valiant Ambition

In the history of the American Revolution, two figures stand in stark contrast to each other: George Washington and Benedict Arnold. In the American imagination, Washington is elevated as an example of sterling character, while Arnold is ostracized to the seventh layer of Dante’s hell. 

But what few Americans know is at the start of the War of Independence, Washington was a blundering general, while Arnold was one of the colonies’ very best. How is it that Washington transformed himself into one of America’s greatest leaders while Arnold ended up betraying his countrymen?

That’s what my guest today explores in his book Valiant Ambition: George Washington, Benedict Arnold, and the Fate of the American RevolutionHis name is Nathaniel Philbrick and today on the show we discuss the evolution of Washington as a general and a statesman, Benedict Arnold’s amazing, but often forgotten battlefield exploits for the American cause, and how Arnold’s valiant ambition turned into a vain and treacherous appetite that led to his downfall. Along the way, Nathaniel and I talk about the life lessons we can take from these two eminent revolutionaries. 

Show Highlights

  • Why Philbrick’s mother was a huge fan of Benedict Arnold
  • Washington’s short-sighted and risky approach to battle at the beginning of the Revolutionary War
  • How Washington was able to go against his natural aggressive instinct and his pride in order to switch to a more defensive strategy
  • Why Washington’s ability to control his emotions and impulses made him a genius politician
  • Why Benedict Arnold was one of the great American generals in the Revolution and was considered the “American Hannibal”
  • The slights that Arnold received at the hands of the Continental Congress that sowed the seeds of his treason
  • Why Arnold’s inability to control his passion and ambition led to his treacherous downfall
  • The civil war among the colonies that was going on at the same time as the fight against the British
  • Why Arnold thought his act of treason was actually an act of patriotism
  • Arnold’s wife’s influence on his decision to surrender West Point to the British
  • How the uncovering of Arnold’s treacherous plot happened by pure chance
  • Why Arnold’s treason was the best thing that could have happened to the revolutionary cause
  • And much more!

Resources/Studies/People Mentioned in Podcast

Valiant ambition book cover, by nathaniel philbrick.

Valiant Ambition is a fantastic read. The battle scenes are riveting, but the best part of this book is the character analysis Philbrick provides of both Washington and Arnold. The leadership evolution of Washington is something to be admired, while the treacherous ambition of Arnold should serve as a warning to us all.

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Read the Transcript

Brett McKay: Welcome to another edition of the Art of Manliness podcast. In the history of the American Revolution two figures stand in stark contrast to each other. George Washington and Benedict Arnold. In the American imagination Washington is elevated as an example of sterling character while Arnold is ostracized to the seven layer of Dante’s hell.

What few Americans know is that at the start of the war of Independence, Washington was actually a blundering General while Arnold was one of the colony’s very best. How is it that Washington transformed himself into one of America’s greatest leaders while Arnold ended up betraying his countrymen? Well, that’s what my guest today explores in his book Valiant Ambition: George Washington, Benedict Arnold and the Fate of the American Revolution, his name is Nathaniel Philbrick, and today on the show we discuss the evolution of Washington as a General and a statesman, Benedict Arnold’s amazing but often forgotten battlefield exploits for the American cause, and how Arnold’s Valiant Ambition turned into a vain and treacherous appetite that led to his downfall. Along the way Nathaniel and I talk about the life lessons we can take from these two eminent revolutionaries. Really great podcast, after the show’s over make sure you check out the show notes at AOM.IS/ambition for links to resources that we discuss in the show so you can delve deeper into this topic. Nathaniel Philbrick, welcome to the show.

Philbrick: It’s great to be with you.

Brett McKay: Your latest book … You’ve written a lot of great historical books. You’re latest one is called Valiant Ambition, where you follow the military careers of two of the revolutionary war’s most well-known names, George Washington and Benedict Arnold. I’m curious, what inspired you to dig into the history of how these men developed into the men we know of today. Washington turned into the great General that we know as today, and how Arnold turned into America’s most infamous traitor.

Philbrick: It’s really kind of two sources to that. My previous book was called Bunker Hill, which describes as the title might suggest, the outbreak of the revolution in the Boston area. The book sort of ends with the arrival of George Washington, who takes over the Continental Army during the siege of Boston. It was with the conclusion of that book that I realized I need to follow George Washington. This is not the Washington that peers at us from the dollar bill, sort of the staid pragmatist that looks like the rock upon which this country’s been founded. Washington, at the beginning of the Revolution was in his early forties, red haired, fiery. By natural temperament, very aggressive. He wanted to attack the British that were holed up in Boston, even if this meant burning the city to the ground. He just wanted to end it all in one very risky stroke. He would repeatedly bring this proposal to his council of war, and every time the generals would turn it down as basically madness.

This is a Washington I had not grown up with. I knew I wanted to follow him, so the question for me was who to pair him up with? Because I also knew that the middle years of the Revolution were very different from what I think most of us assume the Revolution to be. Sort of this each battle’s a stepping stone to God ordained victory. Instead, sort of the gaffe came out of the Revolution and it became this stalemate in which Americans showed much more interest in fighting themselves than the British and I saw how to get at this dark under belly. My mother, when I was growing up in the sixties and seventies, was a huge fan of Benedict Arnold. My mom was kind of a renegade herself, and she always said that Arnold had gotten a bum rap. That there were reasons why he did this, and that your teachers should teach you this. I would always say, “Mom, Arnold personifies evil. What are you talking about?” I am here before you today to say that mom was right.

I realized that I had had this exposure to Arnold as a kid, and I realized that’s the guy to go with. That’s the guy to pair with Washington. What I do in Valiant Ambition is follow four years of Arnold at his highest, because he was our best battlefield general in the beginning, but he would have his reasons to become increasingly embittered with the American cause, and ultimately four years later he would decide to turn traitor. I wanted to follow those two very different characters along very different paths.

Brett McKay: Yeah, that’s what … It really opened my eyes to assumptions that I had. You even start the book with going back to Washington. You talk about how, I think, one of the Secretaries of the Continental Congress, he had this journal where he talked about the foibles of Washington, and he thought about publishing. That time, Washington already had been … The apotheosis of Washington had already happened and we had this myth, and he’s just, “No, I can’t undo this myth, it’s good for the country,” so he didn’t publish it. You said, yeah, Washington, at the very beginning of the war, lacked a bit of military acumen. Didn’t have that pragmatic approach that he had. Are there any specific examples where you talk about in the book, the four years you discuss, where Washington showed a lack of military acumen that actually hurt the Revolutionary cause?

Philbrick: Yeah, from really where the book begins, which is just after the siege of Boston. The British now have turned their sights on New York, and Washington is dug into New York and the high ground in Brooklyn on Long Island. The British have thrown a huge force at America, 3,400 hundred vessels, 34,000 sailors and soldiers. This is the largest invasionary force Britain will mount until World War I. It’s just a huge army that Washington has to deal with, and he had no experience leading a large army in battle. No one in the American army had that kind of experience. As I said before, he was by temperament aggressive. Even though his army was completely over matched by the British, he was determined to fight. He puts his army in a very risky position in Long Island, and he’s completely out-generaled by his British counterpart, General Howe, in a flanking maneuver. Howe had the opportunity to completely destroy Washington’s army, but for the Howe brothers, because his older brother was the Admiral that was in charge of the British fleet, were hopeful that they could humiliate the American army to the point that they were forced to negotiate a peace.

They really felt that by destroying the American army they would hopelessly embitter the American people, and ultimately make reconciliation impossible. You could argue that if not for Howe, Washington would have probably lost his army right there at the Battle of Long Island. Howe gave him the opportunity to escape at night in a brilliant retreat across the East River, and eventually … And yet he persisted in hanging out in New York and trying to defend that. Ultimately he would be forced to retreat. He would have that great comeback at Trenton in Princeton, but the following year, when he was defending Philadelphia from Howe’s army that was now marching towards Philadelphia which is the seat of the Continental Congress, once again Washington at the battles of Brandywine and Germantown surrenders to his naturally aggressive side. As a consequence puts his army in very dangerous positions and suffers reversals that ultimately allow the British to take Philadelphia.

It’s only after this, in the winter of 1777, ’78 while he’s holed up at Valley Forge, that Washington begins to realize, “Okay, I really need to commit to a different kind of strategy. I want to fight, but this is not the best thing for my country, given the state of the army. I need to fight a defensive war, a war of attrition.” What he calls a war of posts. It’s not what he wants to do, it’s not the way he’s wired, but it’s the way he will then proceed for the next years of the War of Independence. It’s kind of extraordinary. There are very few leaders who can go against the very essence of who they are because they know it’s the right thing to do, and Washington was one of those unusual people.

Brett McKay: That’s the moment when he turned into the pragmatic George Washington that we know today.

Philbrick: One of the things, he had his weaknesses as a military commander, but he was an absolute genius as a politician. What happens is, as the war devolves into a stalemate, where each battle really doesn’t do much to really move anything in any direction, it’s Washington’s ability to deal with politicians, with officers who are in-fighting. It’s his political skills that really rise to the fore, and he emerges as that one person capable of holding all of this together.

Brett McKay: There is great examples of that political skill and action where … I think Washington intercepted a note where one of the generals was bad mouthing him, and he saw it, and he passed it along to the guy who was supposed to get it, and he left a note … Kind of, sort of, passive aggressive. It shut the whole thing down. Everyone just backed away.

Philbrick: Right, and this is during the terrible retreat across New Jersey, in the fall of 1776. He’s at his absolute lowest point. Trenton is to come in just a month’s time, but at this point he’s at his lowest, and it’s correspondence for Joseph Reed, his adjutant general, the person upon whom he depends the most. The closest person in his military family. Reed is away from headquarters so Washington opens it, and learns that Reed, unknown to him, has been in correspondence with Charles Lee, the second ranking general in the American army, and complaining about Washington for his indecisiveness, and suggesting to Lee that come winter that Lee go South and organize a new army. This is not good news. For most people it would be crushing news that would probably inspire a good amount of anger. Washington doubtless felt that anger, but instead of outwardly expressing it, he’s brilliant.

He re-seals the letter and sends it to Reed with an accompanying note saying, “Assuming this came for you, assuming it was official business, I opened it as usual. Realizing it was something else, my apologies,” and he leaves Reed to twist in the icy emptiness of his withheld wrath. Man, does he get the message. Those are the political skills that would really serve him, and our country, so well in the years to come.

Brett McKay: Not only did Washington have this fiery temperament that wanted him to … He wanted to attack all the time, but I guess throughout the book, this whole idea of valiant ambition, all these generals had it in spades, and there was this social pressure to fight with honor, and to show yourself a man. I imagine that was a lot of the pressure that Washington felt, too, but he had to say, “No, I’m not going to take part in that, I’m going to switch to this other strategy because it’s for the good of the country.”

Philbrick: Right, and it killed him, because many of his own officers would say, “What are you doing? Why isn’t he going after them?” Politicians who really had no clue as to what was going on militarily, but just wanted things to go as well as possible, criticized him. It was a very difficult position to take. Yet, ultimately, after two years of learning it the hard way, he committed to it. It’s the ultimate … It’s so easy to surrender to our impulses in a fit of anger and pique, but Washington learned, “Nope. I’m going to take the higher ground. I’m going to keep the long view ahead of me.” We really owe the fact that we have a country to Washington’s strength of character in this regard.

Brett McKay: The guy you juxtaposed Washington to was Benedict Arnold. This is a guy who seemed like couldn’t put a check on his temperament and his ambition. What’s interesting in the book though, as you said, we had this idea that Benedict Arnold, he was born a traitor, like he was predestined to go to Dante’s seventh layer of hell. You highlight in great detail before Arnold turned into a traitor he was one of America’s great revolutionary war generals, and I think this is forgotten. Can you take us through some of Arnold’s contributions to the American cause before he committed treason?

Philbrick: Yeah. It’s kind of amazing. In the first years of the revolution there was no one better on the battlefield than Arnold. He learns of Lexington and Concord, and he’s in New Haven, and he realizes that at the southern end of Lake Champlain is Fort Ticonderoga. A lightly held British fortress that contains all of these cannons that would be of huge help to the American cause, and it’s also an important strategic point. So he proposes to the officials in Boston that he take Fort Ticonderoga. By this time, others have heard about the idea, and he ends up having to team up with Ethan Allen and the Green Mountain Boys, and they famously, side by side take Fort Ticonderoga. While Ethan Allen and the Green Mountain Boys are getting drunk on the British liquor supply, Arnold commandeers a loyalist’s schooners, sails up the full 100 mile lake of Lake Champlain and attacks a small British force at St. John’s in Canada, and takes what vessels they have, destroys what he can’t take with him, and now America has command of Lake Champlain. An absolutely essential quarter of water that we need to command.

He does that, and he then goes to Boston where now Washington is the commander of the American army. Washington’s stuck in the siege of Boston, but he sends Arnold on an impossible mission to try to take Quebec. This requires him to go overland, through Maine. I’ve actually followed Arnold’s trail through the backwoods of Maine, there’s still nothing up there to this day. There’s a sign post, it has Arnold’s name on it because he was apparently the last person to go through there, but he loses a third of his soldiers to desertion and death, staggers out of the wilderness and is there at Quebec. He’s heralded as the American Hannibal. He’s ultimately unsuccessful in taking Quebec, no fault of his own. He grievously injured, but he pulls himself together. Then in the fall of ’76 he fights the Battle of Valcour Island, the greatest Naval battle that no one’s ever heard of, fought on Lake Champlain.

Washington has lost New York by this time. Arnold, by preventing the British from taking Fort Ticonderoga, saves America. If they had taken that fort and linked up with Howe in New York it would have all been over. Then that leads, a year later, to the Battle of Saratoga. The great victory in which the French are convinced to come into the war on our side. It was Arnold’s soldiers that were responsible for it. There’s really no one, short of Washington, who’s doing more than Arnold, to do all this. As you said, he was passionate. He couldn’t control himself the way Washington could when he was off the battlefield. Man, our country owed him a lot in the first years of the Revolution.

Brett McKay: I guess where the seeds of Arnold’s treasonous decision was he had these great victories, but it seemed like he perceived that he wasn’t getting the due respect that he thought he deserved from other generals, and also the Continental Congress. What were some of these sleights that Arnold experienced from these generals that kind of sowed his treason.

Philbrick: There are really two events that had a lot to do with it. The first was after stopping the British from taking Fort Ticonderoga at the Battle of Valcour, he was up for promotion. He was our highest ranking brigadier general with the best record, but the Continental Congress that reserved the right to pick major generals determined that each state should get two of them. Since Arnold’s home state of Connecticut already had two, he would be overlooked and five generals who ranked below him would be elevated past him to major general. This angered him. It would have angered anyone. It greatly upset Washington, who realized that Arnold was his best battlefield general at this time. This began his questioning, why am I doing this? He’d also given a lot of his personal fortune to the cause in those first years in Canada, and the Continental Congress showed no interest in compensating him.

It would really be at the Battle of Saratoga in October of 1777 where Arnold would suffer the experience that would really start his spiral down into treason. His commanding officer was Horatio Gates, who was concerned that Arnold, with his reputation for aggressiveness and success on the battlefield, was a threat to stealing the glory from him. What Gates did was instigate a blowup with Arnold. There were two battles to the Battle of Saratoga. The first, Battle of Freeman’s farm, it would be Arnold’s soldiers that would deliver a devastating blow to the British and sent them reeling. In his official account of the battle, Gates chose not to mention Arnold. Gates knew Arnold very well, had been with him on Lake Champlain the previous year, and new just what buttons to push when it came to a guy of such a passionate nature. They have this violent argument and Arnold is out of the Norther Army. This, however, does not prevent him from appearing on the battlefield in the final climactic Battle of Bemis Heights.

It’s Arnold, at the very end, leads this amazing charge to the rear entrance of a British redoubt. Enters on his horse, waving his sword, commands them to surrender, and he is shot with a musket ball fired by a German soldier that fractures his left thigh, kills his horse, which collapses on top of his injured leg. He’s just lying there and one of his young officers from New Hampshire, who’d been with him since Quebec and says, “Are you badly hurt?” He says, “In the left leg. I wish the musket ball had gone through my heart.” He knew that, here his left leg was going to be in very bad shape. He was going to be in a hospital bed for months ahead, and Gates was going to be the hero of Saratoga. Really, “Why am I doing this?” He would eventually spend that winter in a hospital bed in Albany. The leg that would emerge from the fracture box that they attached to it would be two inches shorter. It would be more than year before he could walk unassisted, and he began to wonder, “Why am I doing this? Continental Congress doesn’t give me the respect I deserve.”

By that time they give him his promotion, but it was too little, too late. Gates had messed with his head, and he had suffered this terrible, debilitating physical injury. It was as much a psychic would as it was a physical injury. So he began to wonder, “Why am I doing this?” This began his gradual creep towards treason.

Brett McKay: I think the other thing you do a really good job of highlighting in the book is that underneath these sleights that Arnold was experiencing that contributed to his decision to become a traitor, was that during this time in the war, as you said earlier, the Colonies were fighting each other, basically. They were like their own worst enemies. How did that, that acrimony that existed between the colonies also contribute to his decision to commit treason?

Philbrick: Yeah, because there was war against Great Britain, but there was also civil war going on. The American people were showing much more interest in fighting each other than the British. As Arnold’s becoming increasingly bitter about his own treatment he’s watching his country falling apart. The Continental Congress does not have the power to tax the American people directly, so Washington’s army doesn’t have the funds it needs to fight. By fall of 1780 it really looks like if somehow Washington can win this war, will there be a country left to claim victory? We now look back and see this as God ordained, but in the middle of it it looked like the American people had really turned their backs on the vow they had made to one another with the Declaration of Independence. From Arnold’s point of view he began to think, “Well, since the Continental Congress is no one to trust when it comes to the welfare of this country, it’s time to bring the British back. We’ve defaulted on the pledge we made to ourselves. Let’s bring the British back to restore the freedoms we enjoyed before this misbegotten revolution.”

From his standpoint, what the others would regard as an act of treason, an attempt to sell West Point to the British, he saw it as an act of patriotism. That it was up to someone like him to restore the government that had been fallen, because the American people had proven incapable of governing themselves.

Brett McKay: At what point did Arnold decide to betray his country? I thought this was interesting, too. What role did his wife play in his betrayal?

Philbrick: Arnold … Spouses have a big influence on how people think. Arnold was the hero of Saratoga. They had been forced to evacuate. With the entrance of France, after the battle of Saratoga they needed to consolidate their forces in New York, so Arnold became the commander of this war torn city where there was literally fighting in the streets between patriots and more conservative, loyalist leaning citizens. Arnold, being the controversial person he was, was soon surrounded in controversy. He was really unhappy with what was going on in the country, and personally, but he had fallen in love. A girl literally half his age, 18 year old Peggy Shippen. He was 36, a widower with three young sons, and they fell in love. Her family was well-to-do Philadelphians who had had royal connections prior to the revolution. During the British occupation she and her sisters had enjoyed socializing with the British officers, one of whom, Major John Andre, had done a sketch of her that just shows how beautiful a woman she really was.

Within a month of their marriage Arnold would send his first feelers to the British who were now in New York, and that feeler would go to none other than John Andre, the officer whom Peggy had befriended and would become the British spy chief. Over the next year and a half they would negotiate back and forth with Arnold wrangling command of West Point, the most important port for us in America, and scheming to turn that over to the British.

Brett McKay: He made that decision to give over West Point, it failed. I guess we won’t go into this, because we’re almost out of time, but how it failed just seemed like it was like pure chance and pure luck that this-

Philbrick: Absolutely. The thing about Arnold, he was a good battlefield general, and he was pretty darn good as a scheming traitor. He had been in negotiations for more than a year, and yet the very extensive spy network that Washington and others had put together had no notion, no clue of what Arnold was trying to do. He and Andre meet at night on the banks of the Hudson River, exchange the documents that are crucial to the taking of West Point, it’s all about to happen. Andre needs to get back to British occupied New York to make it happen, but he’s captured by three militia men, and it’s only that that foiled what might have been the plot that ended … That made Great Britain victorious.

Brett McKay: Then, what I thought was interesting in the book, is that you argue that Arnold committing treason was probably the best thing that could have happened to the Americans. Why was his treason such a boon to the Revolutionary cause?

Philbrick: By the fall of 1780 the American war effort had cratered. It seemed like the American people had just given up. They hadn’t been willing to pay taxes to the British, now they weren’t willing to pay taxes required to fund the army needed to win them independence, and they were fracturing into thirteen independent colonies instead of functioning as a country. It was the revelation of Arnold’s betrayal, this great hero who had tried to turn over West Point to the British, this had a galvanizing affect. Arnold would be burned in effigy in towns up and down the Eastern seaboard. This was a true wake up call, and I don’t think it’s an accident that within a year’s time America would enjoy the incredible victory at York Town that would make the victory in the War of Independence inevitable. It’s interesting, Arnold would become a British brigadier general, and be sent down to Virginia, and Washington was, by this time, very angry with Arnold and making a real personal cause to get him, sent Lafayette, the French general who had become a virtual son to him, down to get him.

This begins the movement of troops that would ultimately culminate in the great victory at York Town. I think ultimately you could argue that, in the early years of the revolution Arnold did more than anyone, short of Washington, for America, but it was as a traitor that he really made possible ultimate victory.

Brett McKay: My guest today was Nathaniel Philbrick, he’s the author of the book Valiant Ambition, it’s available on and bookstores everywhere. Also, if you want to delve deeper into this topic check out our show notes at AOM.IS/ambition. Well that wraps up another edition of the Art of Manliness podcast. For more manly tips and advice make sure to check out the art of manliness website at, and if you enjoy the show I’d appreciate if you’d give us a review on iTunes, it helps us out a lot. As always, thank you for your continued support, and until next time this is Brett McKay telling you to stay manly.

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