As you’ve likely heard — including on our own Member Feed — the Department of the Treasury is planning to replace the portrait of Alexander Hamilton on the $10 bill, very likely with Harriet Tubman’s. All due respect to Mrs. Tubman — who deserves it greatly — but this is an incredible travesty. For all his many faults, Hamilton is one of the most extraordinary members of one of the most extraordinary generations in world history — and a handsome devil at that.

It’s difficult to decide which is more amazing: that Hamilton accomplished so much during his 51 years of life, or that he managed to make it that long before getting himself killed. While many of the incidents of his life are extremely well known — his work as Washington’s aide and spymaster, his contributions to the Constitution, the Federalist Papers, his remarkable and controversial tenure at Treasury, his affair with Maria Reynolds, his battles with Thomas Jefferson and Aaron Burr — his life also has a lot of chapters that are more obscure. Here are four of them:

Opposition to Slavery

Of the Six Big Founders, only Hamilton was consistently opposed to slavery. Having grown up in the Caribbean, he’d seen its darkest side — sugar plantations that were about one step removed from death camps — and also had dealings with freed blacks and mulattoes. The experience appeared to have never left him. Throughout his career, he made various public compromises regarding slavery, but then redoubled his private efforts against the institution. Unlike Jefferson, who sometimes expressed a guilty conscience on the matter, Hamilton actually took action.

In 1779, he and his friend John Laurens petitioned George Washington for permission to form a regiment of emancipated slaves, which Washington turned down. In 1785, he cofounded the New York Manumission Society, a moderate abolitionist movement that held anti-slavery lectures and successfully lobbied for legislation making emancipation easier (they unsuccessfully pushed for a sunsetting of slavery within the state).

In his later years, Hamilton and his wife, Elizabeth, founded a trade school for freed blacks. It’s also likely that his efforts contributed to Washington’s nearly unprecedented decision to free his slaves upon his death (actually Martha’s, according to his will, but she freed most of them earlier) and set up an endowment for them.

Was Present at Benedict Arnold’s Betrayal (And Was Totally Duped by Mrs. Arnold)

Benedict Arnold’s plan had been to surrender West Point while Washington was staying there, giving the British not only a strategic fort, but also the commander-in-chief of the Continental Army. Unfortunately for Arnold, his British contact was captured (with the fort’s plans in his shoe)  just before Washington arrived, and Arnold only learned of that fact while breakfasting with Washington’s aides, Hamilton and James McHenry. Believing he would soon be arrested, Arnold excused himself, went upstairs to see his wife — who had likely pushed her husband into being a turncoat — and slipped out the window.

It wasn’t until later that morning that Washington and Hamilton connected the dots and realized that Arnold was behind the whole thing. Running upstairs, they found a (seemingly) hysterical Peggy Arnold who put on a very convincing show for them that stalled them for time. As Hamilton wrote to Elizabeth, then his fiancee:

It was the most affecting scene I ever was witness to…The General went up to see her, and she upbraided him for being in a plot to murder her child. One moment she raved, another she melted into tears. Sometimes she pressed her infant to her bosom, and lamented its fate, occasioned by the imprudence of its father, in a manner that would have pierced insensibility itself. All the sweetness of beauty, all the tenderness of a wife, and all the fondness of a mother showed themselves in her appearance and conduct…

Could I forgive Arnold for sacrificing his honor, reputation, and duty I could not forgive him for acting a part that must have forfeited the esteem of so fine a woman. At present she almost forgets his crime in his misfortune, and her horror at the guilt of the traitor is lost in her love of the man. But a virtuous mind cannot long esteem a base one, and time will make her despise, if it cannot make her hate.

I’d wager that Elizabeth and her sisters saw through the charade before finishing Hamilton’s letter with much rolling of eyes.

Peggy subsequently had a good laugh over the matter with her friend, Theodosia Prevost, the wife of a loyalist officer and the future Mrs. Aaron Burr.

Nearly Got Into A Duel With James Monroe

In 1792, James Reynolds — husband and sometime pimp of Maria, the woman with whom Hamilton had an affair — was arrested on suspicion of pension fraud. While in jail, he made dramatic insinuations that he could “make disclosures injurious to the character of some head of a department” — i.e., Hamilton — which he implied he would be willing to share in exchange for his release. Reynolds’ accomplice, Jacob Clingman, was able to get the attention of House Speaker Frederick Muhlenberg (whom he once clerked for) after showing him letters between Hamilton and Reynolds.

Feeling it his duty to investigate, Muhlenberg gathered Rep. Abraham Venerable and Sen. James Monroe and went to speak with Hamilton. The secretary was initially rude to them, but his demeanor changed when they produced documents between him and Reynolds. Hamilton become quiet and agreed to meet them later that evening. After categorically denying the corruption, Hamilton amazed them by confessing his affair with Mrs. Reynolds, producing document after document proving both Maria’s infatuation with him and Reynolds’ subsequent blackmailing. An embarrassed Muhlenberg tried to stop the performance, saying the matter was a private issue and closed so far as he was concerned, but Hamilton continued and insisted that the speaker and the others take the letters and documents to review later.

Monroe took them and likely gave them to House clerk John Beckley, a fellow Jefferson partisan. Within 48 hours of Hamilton’s interview with the legislators in Philadelphia, Thomas Jefferson not only knew about the matter, but had recorded it in his journal.

A little over two years later, after the affair went public in James Callender’s History of the United States, Hamilton knew someone had betrayed the gentlemen’s confidence he had received from the legislators. Soon realizing that it must have been Monroe — the only of the three to decline to respond to Hamilton’s letters, despite boarding just down the street from Hamilton’s house — a furious Hamilton stormed over to see Monroe, who played it cool and calm but denied leaking the documents. Then this happened:

Hamilton: Your representation [of this matter] is totally false.

[Both jumped to their feet.]

Monroe: You say I represented falsely; you are a scoundrel.

Hamilton: I will meet you like a gentleman.

Monroe: I am ready. Get your pistols.

Fortunately, their friends pulled them apart before the two came to blows and each selected a second to represent him in the ensuing affair of honor. Fortunately — and as usually happened in these things — cooler heads prevailed, mostly due to the efforts of Monroe’s second: none other than Senator Aaron Burr, who even went so far as to refuse to deliver some of Monroe’s more incendiary letters. The business permanently ruined Burr’s estimation of Monroe, with whom he’d been very friendly before.

Got Along With Burr Pretty Well For Most of Their Lives

Burr and Hamilton likely met in 1774, shortly after Burr graduated from the College of New Jersey (now Princeton) and while Hamilton was studying at its preparatory academy. Amazingly, their connection goes back even further: Hamilton’s tutor on St. Croix had studied under Burr’s father — Rev. Aaron Burr, Sr. — and it’s likely that Hamilton was familiar with the name before he ever set foot on American soil. During the war, they likely encountered each other again during the Battle of New York, and briefly served together on Washington’s staff.

Over the next 20 years, they were often in court together– usually, though not always, on opposite sides — and active in various New York charities and civic organizations. Though hardly allies, neither would have considered the other his enemy. During the Quasi-War, Hamilton enthusiastically recommended Burr for a commission as a brigadier general, through Washington turned him down. In the spring of 1800, they served as co-counsel on a salacious murder trial — they won — while also running their respective parties’ campaigns for state legislature (the members of which would subsequently elect the state’s electoral college electors).

Generally, Hamilton liked Burr fine, so long as the latter knew his place (i.e., beneath Hamilton) and often recommended him for office and promotion. But whenever he felt that Burr might eclipse him, Hamilton began feeling qualms about Burr’s ethics and morals, many of them justified — but also rather opportunistic.

It was only after the election of 1800 that they became permanent foes.