Alexander Hamilton And The First Five Presidents

His love-hate (mostly hate) relationship with the first presidents.

Though Alexander Hamilton was never president himself, he had more intense relationships with the first five US presidents than anyone else, with the possible exception of the Marquis de Lafayette.

The key difference is that everyone loved Lafayette.

#1 George Washington

Hamilton served directly under Washington in the Revolutionary War and became his first Secretary of the Treasury. He was Washington’s advisor, ghostwriter, and chief policymaker.

They were the father and son they both never had, and together they helped define the capitalist future of the United States for hundreds of years. Theirs is a love story you can take to the bank.

#2 John Adams

Adams and Hamilton were members of the same Federalist Party, which implies they should have been aligned in some kind of philosophical or political partnership, right? Not in Hamilton’s world.

Hamilton hated Adams, so much so that he published a pamphlet in 1800 all about how re-electing Adams would be a catastrophic choice. This all but ensured a victory for the opposing Democratic-Republican Party. (He was much better at finance than he was politics.)

The hatred was mutual. In a wonderfully bizarre letter written two years after Hamilton’s death, Adams gleefully blamed all of Hamilton’s problems on “a superabundance of secretions which he could not find whores enough to draw off.”

Hamilton had a way of bringing out the best in people.

#3 Thomas Jefferson

When George Washington chose the nation’s first Cabinet, he selected Jefferson as his Secretary of State and Hamilton as his Secretary of the Treasury. He was so optimistic about his choices he told Lafayette, “I feel myself supported by able co-adjutors, who harmonize extremely well together.”

A couple years later, the “harmony” between Hamilton and Jefferson must have been deafening.

Hamilton and Jefferson were so diametrically opposed that they ended up defining the duality of the early United States – the principles of:

Jeffersonianism — a minimum of federal power, individual rights, the idealism of the yeoman farmer; and

Hamiltonianism — a strong central government with a commercial and industrial economy, skeptical of giving too much power to the common man.

(Poor John Adams got nothing named after him.)

Despite their differences, Jefferson owes his presidency to Hamilton. After Hamilton helped knock Adams out of contention with his “Why John Adams Sucks” pamphlet, the election of 1800 ended in a tie between Jefferson and Burr. It was Hamilton’s lukewarm endorsement of Jefferson that helped the election go Jefferson’s way.

That may be one reason that Jefferson, unlike Adams, had some positive words for Hamilton after his death. He wrote:

“Hamilton was indeed a singular character of acute understanding, disinterested, honest, and honorable in all private transactions, amiable in society, and duly valuing virtue in private life, yet so bewitched & perverted by the British example, as to be under thorough conviction that corruption was essential to the government of a nation.”

Okay, mostly positive.

By the way, “Bewitched & Perverted” sounds like an awesome band name. I could see them opening up for “Superabundance of Secretions.” Or maybe both could be song titles in a Broadway sequel to Hamilton where people just talk shit about the dead founder for three hours. (Call me, Lin – I’ve got so many rhymes for secretions!)

Engraving of the Hamilton-Burr Duel. Fun fact: In addition to his relationship to the presidents, Hamilton also has the distinction of being the first person shot by a sitting vice president – a record he held until 2006 when Dick Cheney shot 78-year-old lawyer Harry Whittington in the face during a quail hunt.

#4 James Madison

Hamilton and Madison started out as a dynamic duo. When they weren’t working together to get the Constitution ratified by cranking out the majority of the Federalist Papers, they were literally petting monkeys together on the streets of New York.

But it wasn’t meant to be. They had a nasty breakup over the direction of their young country, with Hamilton pushing for a British banking system and federal power that didn’t sit well with the southern Democratic-Republicans whose economy depended on slaves and pretending debts weren’t real.

Hamilton is the man most responsible for transforming Madison from the author of the Federalist Papers to the #1 enemy of the Federalist Party.

#5 James Monroe

Monroe gets less love and attention from history, but he played a significant role in Hamilton’s undoing. It was Monroe who confronted Hamilton about suspicious payments, and it was Monroe to whom Hamilton confessed his affair with Maria Reynolds to clear his name of any financial misdeeds.

Monroe probably kept this info secret, but it leaked anyway so Hamilton challenged Monroe to duel. In an age of coded duel language about “satisfaction” and “interviews,” Monroe’s no-bullshit response was simply “I am ready get your pistols.”

The person who stopped them from dueling in 1797?

None other than Aaron Burr, sir.


Interested in why Alexander Hamilton and John Adams hated each other? Listen to the Plodding Through The Presidents podcast episode “Alexander Hamilton & John Adams: A Superabundance of Hate where we dig into just why these men loathed each other more than any other founders, in their own nasty words.



  1. Jantique Fielding
    January 11, 2019 / 9:51 am

    Adams’s letter about Hamilton’s “secretions” is funny. Your comment on it is funnier! 😁 And “… able co-adjutors, who harmonize extremely well together.” Was Washington on DRUGS?! Raising that “wacky tobacky” at Mt. Vernon?! 😉🤣😁

    But – suppose Hamilton and Madison HAD dueled in 1797? If Madison had been seriously injured or killed and NOT become President – no “Mr. Madison’s War?” But if Hamilton had been killed – might Aaron Burr had become President?! Fascinating “what-ifs”! 🤔

  2. January 11, 2019 / 7:47 pm

    Fantastic post! Thank you!

  3. Carly
    January 12, 2019 / 6:47 pm

    The last one with James Monroe should have been a song in Hamilton. It would have been so ironic and meta

    • Evan
      September 1, 2020 / 11:32 am

      It did. “We Know” is this premise, but with more familiar characters.

  4. Charlie MacNeill
    July 10, 2020 / 4:48 pm

    Another great band name to come out of the founding would be “Gouverneur Morris & The Committee on Style” perhaps singing their hit “I’M NOT YOUR STEPPING STONE” which was based on Hamilton’s last words. (Apologies to Paul Revere & The Raiders…and everybody else.)

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