It’s no secret Hamilton was hypersensitive, and out of the Founders by far had the most challenges under his belt. He only ever saw the dueling field twice (once as Laurens’s second in his duel with Charles Lee, and then as the principal against Burr).
Here’s a list of the people he challenged and for what reason:
Reverend William Gordon (1779) - Accused of wanting to overthrow the government
Aedanus Burke (1790) - Accused of lying
John Francis Mercer (1792-93) -Accused of buying government debt at inflated prices to help speculators
James Nicholson (1795) - Accused of being corrupt and a coward
Republican Party (1795) - Bad day
Maturin Livingston (1795 and 1796) - Accepted above challenge
James Monroe (1797) - Accused of speculation and slander
John Adams (1800) - Accused of everything, but specifically of being a member of a British faction
Ebenezer Purdy/George Clinton (1804) - Accused of plotting to put a son of George III on an American throne in exchange for Canada
Aaron Burr (1804) - Accused of character defamation through libel. Only instance where Hamilton did not initiate the challenge.
Order of events on July 18th, 1795:
- Hamilton tries to stop a fight between James Nicholson and another Federalist
- Of course it goes terribly
- Nicholson accuses Hamilton of being a coward who dodges duels
- Hamilton fails utterly as a peacekeeper and says, “I’ll show you who dodges duels, prepare to fucking duel”
- Leaves angry
- Runs into a group of Republicans
- He’s on a roll, he challenges them too
- All of them.
- Maturin Livingston takes him up on it
- Hamilton: “Well, I can’t today, I already made plans with Nicholson”