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.
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.
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.”
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.
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.
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.
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.
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.
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.
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.
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.