Biggest jerk of the Revolution?


July 11, 2016
by Editors Also by this Author


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Biggest jerk of the Revolution? Who seemed to be the most despicable person of the era? Why?


This award goes to Benedict Arnold, but not because he changed sides (lots of people did that); instead, the reasons are twofold:

Regardless of his tactical skills and overall abilities on the battlefield, many of his peers and superiors disliked him intensely. Some gave explicit reasons, others did not, but it’s very clear that he was a difficult man to work with, a poor team player. He lacked collaboration skills that are essential for an effective military officer. Many officers on both sides didn’t care for each other but managed to work together anyway, whereas Arnold provoked very bitter hatred from many who served with him. He reminds me of some modern business leaders who, although capable of managing companies and amassing wealth, are very hard to get along with. They’re jerks – successful jerks, but jerks nonetheless.

The second reason is more important. The fact that Arnold turned coat is no big deal; a number of American officers did that, as did many soldiers on both sides. Many modern scholars attribute Arnold’s turn to having had his honor slighted by Congress. That’s fine. But an honorable man would have simply rowed out to the British sloop Vulture and offered his services to the other side. Arnold negotiated for money in return for allowing his strategic post to fall to British attack. This is not the action of an honorable man. Imagine if West Point had fallen due to Arnold’s subterfuge – how honorable was it to cause the death, injury or captivity of the men who had faithfully served under him? Arnold’s choice to switch sides can be explained away in terms of personal honor, but his attempted betrayal of his soldiers and subordinates makes him as despicable a man as ever there was.

Jerk, regardless of skills and talents.

Don N. Hagist


The biggest jerk –  and also the most despicable person of the era–  is undoubtedly Major General Charles Lee. Starting in 1776, when he ignored Washington’s orders to join him in New Jersey, he repeatedly demonstrated his low opinion of the commander-in-chief. When he finally brought his troops into the Garden State, he stupidly allowed himself to be captured by British cavalry. When he was exchanged two years later, his ego was undiminished. He advised Congress to abandon a trained regular army and switch to an all guerrilla war. He was convinced Americans could not stand up to British regulars in a face-to-face confrontation. When the British attacked his division at the battle of Monmouth, he ordered a headlong retreat, without even consulting Washington. He then claimed credit for the battle’s outcome! When Washington court-martialed him and Congress upheld the guilty verdict, Lee proceeded to fling abuse at Congress, who dismissed him from the army. Quite simply, the man was a fool.

Thomas Fleming


The most despicable behavior award would have to go to Gen. James Wilkinson. A corrupt, deceitful, two-faced thief is the best descriptor of Wilkinson. He shamelessly took credit for the actual person who collected critical battle-winning intelligence at Saratoga. Receiving a promotion to brigadier general, Wilkinson took nearly three weeks to tell the Continental Congress the victory news due to wooing a woman and setting the groundwork to have George Washington fired. Although drunk a lot, he was soon fired for his cabal activities. Wilkinson’s scathing letter to Congress couldn’t be included in the record because of profanity. In one last chance as clothier general, Wilkinson took thievery to new heights and he resigned. Post-war, the now-militia brigadier general swore allegiance to Spain in exchange for exclusive trade rights.

John Randolph said “Wilkinson is the only man I ever saw who is from the bark to the core a villain.”

John L. Smith, Jr.


Hate to say it, but I’m going with Ethan Allen.  I would not necessarily call him “most” despicable, but he rated right up there as pretty self-serving, -aggrandizing, mean, and endlessly insufferable.  Allen’s egregious abuse of the peaceful, non-threatening Yorker settlers before the war and then his conduct immediately after taking Ft. Ticonderoga as he allowed his men to rampage through the fort and then threaten to kill Arnold hardly coincide with the accolades that history has sought to bestow on him.

In fact, his performance was so bad that he could not even get elected by his own men to a command position within the Vermont militia; not to mention his amateurish failures in trying to capture Montreal and getting captured in the process.  Then, when he returned from captivity in 1778 he continued with his abuse of the Yorkers, not in fighting the war.  Allen angered many at all levels and was, by and large, pretty much a jerk.

Gary Shattuck


Charles Lee and his little doggies never fail to amaze me.  Despite being highly educated, and having record of great achievement, Lee is reported to have been a smelly, disheveled fellow with a reputation as a braggart.  In 1778, he was court-martialed for disobedience of orders in not attacking the enemy; making an unnecessary, disorderly retreat; and was known far and wide for his disrespect to the commander-in-chief.

Kim Burdick


My choice is British Lieutenant General Charles, Earl Cornwallis. He completely let his personal ambition get in the way of his duties. When he returned from England, he said he wanted nothing more than to act as Henry Clinton’s second-in-command. But when news that Clinton’s request to resign the command, made in November 1779, had been rejected, Cornwallis practically threw a tantrum because he lost his chance to get command in America. In the midst of crucial operations against Charleston, he announced that he would no longer consult with Clinton on planning, demanded an independent command, and blamed Clinton for the King’s failure to accept Sir Henry’s resignation, claiming that Clinton must not have been adamant enough in requesting to resign. To top it off, Cornwallis then set about stirring up unrest among the army’s officers, dividing them into factions that negatively impacted future cooperation. Later, Cornwallis ignored Clinton’s orders to hold South Carolina and went charging off into Virginia, communicating directly with London but ignoring his immediate superior. This not only deranged all of Clinton’s plans for the 1781 campaign but cost the British South Carolina and ended with the disaster at Yorktown. A textbook example of how not to be a good subordinate officer.

Jim Piecuch


By far the most despicable major figure in the Revolution was that most famous traitor Benedict Arnold. While other lesser figures may have been more brutal and inhumane in their actions, none reached the level of professional and personal betrayal equal to that of Arnold. For reasons of a personal and ego nature, he volunteered to serve the British for a specific price and additional favorable terms. In return he was willing to betray his country’s cause, betray his command, meaning several thousand troops he lead, and even on a personal level betray his chief protector during his army career, George Washington. In his correspondence to the British of September 15, 1780, he advised where Washington would be staying. If acted upon, this information would have permitted the British to capture him. And, his later military activities for the British in both Connecticut and the Tidewater area of Virginia were purposely brutal in nature against his fellow countrymen.

Ken Daigler


Initially, Gen. Charles Lee comes to mind due to his uncouth manners and likely treason. However the Patriot participants in a particularly egregious incident with Native Americans stand out as the most despicable people. On March 8, 1782, a Pennsylvania militia unit under the direction of Captain David Williamson brutally massacred a non-hostile group of Delaware Indians at the town of Gnadenhutten. The Native Americans did not attempt to defend themselves and almost one hundred men, women and children were killed in cold blood. While both sides perpetrated atrocities, the senseless killing of these peaceable Native Americans served no cause, stained the Patriot’s freedom cause and engendered years of further conflict and retributions.

Gene Procknow


James Wilkinson versus Aaron Burr.  It’s a contest to see which one of these self-servers contributed the least to the success of the Revolution, but the winner by a nose is Wilkinson.  No matter how hard he tried, Wilky couldn’t help being a jerk.  And he was able to fool some of the people some of the time.  Why else would Congress name him a brigadier general?  Maybe this suggests that some leaders in Congress–James Lovell comes to mind–should be included in the jerk category.  However, wherever Wilky went and whomever he served, he caused problems, and never contributed much of anything.

James Kirby Martin


I don’t see how to get past Benedict Arnold as the most despicable Patriot of the revolution.  Not 100% certain if he sold us out for a skirt or if he was simply a man whose loyalty was for sale from the beginning but it really is hard to get more despicable than that.  For the British, I would go with Thomas Brown.  Considered a Loyalist by virtue of having emigrated in 1774, Brown was famously tarred and feathered in the summer of 1775 which seems to have embittered him to the point of leading (by far) all the southern British commanders in hanging Patriots.  Revenge is never a virtue.

Wayne Lynch


I’ll put in a bad word for Benjamin Thompson (1753-1814) of Woburn, Massachusetts. Having married a rich older woman and moved to New Hampshire, in 1774 he was hiring British deserters for his estate, working them so hard they wanted to leave, and then turning them over to the army before he had to pay them. In early 1775 he had an affair with the wife of printer Isaiah Thomas, breaking up that marriage and abandoning his own. When the war started, Massachusetts Patriots locked him up on suspicion; Thompson convinced his old friend Loammi Baldwin, now a lieutenant colonel in the Massachusetts army, to vouch for him. He then traveled around the American lines, sending secret spy reports to the British commander in invisible ink. Fearing exposure, Thompson defected to the Crown outright in the fall of 1775. In London he attached himself to the family of Lord George Germain, the Secretary of State for the colonies. Gossips agreed that Thompson was providing sexual favors for someone—Germain, his wife, his daughter, or some combination. Later Thompson became Germain’s official secretary, making the most of that position. At the end of 1781, just before his patron’s fall from power, Thompson secured a commission as lieutenant-colonel of the King’s American Dragoons. He returned to America to fight, earning notoriety in Huntington, Long Island, for converting the local graveyard and church into a fortification. After the war Thompson, soon better known as Count Rumford, became recognized as a far-seeing social reformer and one of the most brilliant scientists of the age.

J. L. Bell


  • A fun article, though “biggest jerk” and “most despicable person of the era” are not synonymous to me. Charles Lee and Ethan Allen would be among my biggest jerks. Sadly, I agree with the assessment of Benedict Arnold as “most despicable.”

    Sadly, because Arnold contributed so much — certainly far, far more than the terribly despicable James Wilkinson — but ultimately Arnold’s willingness to connive at the deaths of his own men, and potentially Washington, sweeps him, for me, to the top of the despicable class. (The one man who might edge him out in the sweepstakes would be Provost Marshal William Cunningham.)

    I am currently reading Nathaniel Philbrick’s brilliant VALIANT AMBITION, the first book I have read that in my estimation gets the strengths and weaknesses of both Arnold and Washington exactly right.

  • Look at the matter another way: Charles Lee was a much more experienced officer than anyone in the Continental Army, and Washington had lost both New York and Philadelphia; Cornwallis fought many battles while Clinton was safely behind his desk; Arnold had fought in battle and seen his fortune diminished by the war, and Continental money was worthless; Wilkinson joined the army at age eighteen. Each acted as he felt necessary, with the knowledge available at the time, without the benefit of hindsight or twentieth first century ethics. Just a thought to keep in mind.

    1. What’s this about “twentieth century ethics”? Didn’t the 18th century have the concept of Honor (or Honour)? After the Revolution, Benedict Arnold did not do well in England–or Canada. Partly because of his poor business skills–but also because many Brits thought ill of him.

      As the first contributor stated, Arnold could have just switched sides. But he bargained long & hard to undermine the American cause–for money.

  • The reality is that just about every “hero” involved in the American Resolution was far from perfect and every “villain” was not totally imperfect. The events caused many on both sides to do bad things. But, since history is written by the winners, names like Benedict Arnold, Charles Lee, and James Wilkinson come easily to mind. BUT, if the British would have won, the villain list might likely include names like George Washington, Benjamin Franklin, Paul Revere, and Thomas Jefferson. History is not black and white… but, rather, various shades of gray. (Alas, for the Brits, history comes in shades of grey…LOL,)

  • Plenty of candidates but I’d go with Joseph Reed. Among his narrow-minded actions include backstabbing Washington by questioning his leadership in correspondence with General Lee. Then there was that ridiculous self-serving letter to Washington on the eve of the surprise attack on Trenton as if he’s giving advice when the plan was well underway.

    Reed was at his worst as President of the Supreme Executive Council of Pennsylvania soon after the British evacuated Philadelphia. He made an unstable situation much worse with his overzealous persecution of loyalists. In his mind, the states best interest was more important than the nations. Then there were the threats to withhold any assistance from Pennsylvania to the Continental army, which would have been devastating, but that was a whole other petty affair.

  • Gary, I agree that Ethan Allen was highly self serving and self aggrandizing. Further he failed at being a military commander and most of the other things he did as you describe. However he did many tough things so that more reasoned people like Thomas Chittenton and Moses Robinson could form Vermont as a distinct political entity. So as a Patriot seeking independence from Britain, I most whole heartedly agree with you. However, Allen created a spark which ignited the state of Vermont and resulted in its contributions independent of New York. In the end, maybe this is why Ethan Allen’s legacy is so interesting!

    1. Hi Gene,

      I would otherwise agree with what you say regarding Allen having “created a spark,” but his purported contributions are based on the vehement propaganda, obfuscations, distortions of truth, and downright lies he used in vilifying the Yorker situation. Even Allen agreed that what he did was questionable, invoking the word “terrorism” to explain his actions. And with his heavy Onion River investments up for grabs by the British, the Allens rush to protect them reveals a lot of self-serving going on.

      It was because he used such extreme actions that people like the more moderate, and reasonable, Chittenden and Robinson were able to come forward. But theirs was but a substitute to Allen’s extremes as they continued to obstruct the Continental Congress and NY at the expense of the patriot cause. And let us not forget the Haldimand Affair. The basis for the state’s founding has been obscured, at least from my perspective, and I think we need to recognize that the push towards its (not the country’s) independence was based much more on personal interests that on altruism.

      I don’t say these things lightly, having spent the past year and a half researching the foundation of Vermont’s so-called “radical” 1777 Constitution and completing my master’s thesis (all 173 pages, available on request, and now sitting with the Vermont Historical Society and board of directors of the Ethan Allen Homestead with whom I have an excellent pre-existing relationship). This also includes much work in NY colonial court records in NY and here in VT and which corrects many of the misconceptions that Allen’s propaganda created to cast aspersions on the rule of law on the Vermont frontier. He was just wrong in so many ways.

      Much more can be said, but to answer the question posed, “who was the biggest jerk,” I think Allen richly fits the bill. He may not have been despicable (although he did ride around with over a dozen armed men as a bodyguard as he trampled on the Yorker men, women and children), but he fits the bill from my perspective. I agree, his legacy is interesting, but it is not accurately portrayed, and to that I attribute the efforts of nineteenth century revisionist “historians.”

      1. Sounds like a good subject for a popular history–or a film :The Battle of Lake Champlain. Two oversize personalities, Ethan Allen & Benedict Arnold, “co-operating.”

        I’d buy it!

  • why not Banastre tarleton,hated and feared by those colonists….with Canadian Indian bloodthirsty and completely neither dashing or loved, even the loyalists and British Army officers were dismayed by his cruelty and vanity….

    1. Tarleton has gotten a bad rap from American mythology of the Revolution. When one looks only at primary source accounts written during and soon after the war, we find few, if any, indications that “loyalists and British Army officers were dismayed by his cruelty.” Watch for an upcoming article that reveals the real Tarleton, not the cruel caricature of popular biographies and movies.

      1. Not so certain that Tarleton’s reputation isn’t well deserved. That said, I agree that his reputation among his fellow officers wasn’t really about cruelty. However, I think ‘vanity’ might be getting a bit closer to the truth. Tarleton was known to lie in his reports and overstate the exploits of his troops. There are British accounts of Blackstock’s Plantation and Tarrant’s Tavern that show clear doubt about Tarleton’s reports. Some later and others contemporary to the reports themselves. And, of course his attempts to blame everyone but himself for getting outsmarted by Daniel Morgan at Cowpens are well known. But those things speak only to his reputation among fellow British officers. Among the Patriots he did indeed have a reputation for cruelty. Starting with the stories from Monck’s Corner and the massacre at the Waxhaws, Tarleton quickly gained a reputation for a lack charging hard and showing little quarter. Those actions may have only made him a fearsome cavalry officer but Tarleton took things a step further in the Fall of 1780. The British Legion had been virtually invincible all summer. Their victories at Waxhaws and Fishing Creek were legendary in the back country and no doubt Tarleton enjoyed the prestige. However, things turned sour at Charlotte when the regiment refused to charge William Richardson Davie’s militia. With Tarleton sick, they showed a bit of cowardice. Perhaps stinging a bit from that, Tarleton took his next assignment to heart. He was sent after Francis Marion, and, when he failed to catch the ‘Damned old Fox’, Tarleton burned about 30 plantations along the Santee. Not only did his reputation now include a very thorough job of plundering people to the point of starvation, but he started a pattern of more personal vengeance by hanging a young man caught and accused of being a patriot. His losses at Blackstock’s and Cowpens resulted in similar behavior. After three failures in a row, Tarleton sent reports to Cornwallis claiming success (or, in the case of Cowpens, blaming the defeat on others), and then took a bit of personal satisfaction in hanging a Patriot who wasn’t even likely involved. Following his defeat at Cowpens, Tarleton refused to take the field unless Cornwallis gave him a letter exonerating him for the loss. And then, once back in the saddle, his next action was to charge into a mass of fleeing refugees at Tarrant’s Tavern and then claim a nice victory over the Patriot militia. He later described an organized defense, “the militia were vigilant” but he dared to “hazard one charge.” In defiance of his orders and with a cry of ‘remember the Cowpens’, Tarleton led the charge and “killed near 50 on the spot.” A more reliable historian (Charles Stedman) recorded that another officer reported only 10 bodies on the field. According to Patriot accounts, the militia were nothing more than a disorganized bunch of refugees drinking and trying to decide what to do next when Tarleton charged in a dispersed them, followed by yet another round of plundering the refugees of their meager possessions.

        In any event, while I did choose Thomas Brown as a more despicable character than Tarleton, it wasn’t because I feel that Tarleton’s reputation is ill deserved. Quite the contrary, it was simply a matter of numbers and Brown carried the day. 🙂

  • My vote is for Loyalist Joshua Loring, British Commissary General for Prisoners who, together with Captain William Cunningham, Provost, diverted supplies sent for the American POWs and sold them for their own benefit. Despicable Loring blatantly allowed to be cuckolded by his wife with MGen William Howe.

  • Very interesting. I love these specific questions and resulting comments.
    I am looking for resources for the suppliers of cloth and blankets in (Lancaster Co, etc) PA. There was a Clothier General and other officials, but who were the local, colonial manufacturers and suppliers? Has anyone researched this topic?

  • My vote is for Horatio Gates. Appointed a general in 1775, he at first provided useful service to the American cause. He successfully intrigued to replace Philip Schuyler. He commanded the army that captured Burgoyne’s army at Saratoga, but what did Gates actually do? He went nowhere near the fighting at either the first or second battles of Freeman’s Farm. During the second battle he was arguing with the captured Sir Francis Clerke, who later died of his wounds. Soon after, Gates was involved in the Conway Cabal, a plot against George Washington. Against Washington’s advice, Gates was sent south in 1780 to lead the American cause in the south. His army was crushed by Lord Cornwallis at Camden. Gates rode 60 miles to Charlotte NC that same day, leaving his shattered army completely in the lurch. Inexplicably, he rode 120 miles more over the next two days. Gates was also involved in the Newburgh conspiracy in 1783.

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