Alexander Hamilton was a genius. He built the American financial system from scratch, wrote the lion's share of the Federalist Papers, and served as Washington’s right hand. But he was also a disaster. When you look at the James Reynolds letter to Hamilton, you aren’t just looking at a piece of 18th-century mail. You’re looking at the first major political sex scandal in United States history. It’s messy. It’s gritty. It basically reads like a script from a prestige TV drama, except the stakes were the literal survival of a founding father's reputation.
Most people know the broad strokes from the musical. Hamilton meets Maria Reynolds, they have an affair, her husband finds out, and then comes the blackmail. But the actual letters? They are far more desperate and manipulative than most realize. James Reynolds wasn't just a scorned husband. He was a low-level con artist who realized he had the Treasury Secretary of the United States over a barrel.
The Setup: A Knock at the Door
It started in the summer of 1791. Hamilton was at his home in Philadelphia. Maria Reynolds showed up, claiming her husband had abandoned her and she needed money to get back to her family in New York. Hamilton, ever the "helper," visited her later that night with a bank note. You know what happened next.
The affair lasted roughly a year. But it wasn't long before James Reynolds "discovered" the tryst. On December 15, 1791, James sent the first truly damaging James Reynolds letter to Hamilton. This wasn't a letter of outrage. It was a business proposal.
Reynolds wrote that his "tender heart" was crushed. He claimed he could no longer live with Maria, yet he didn't want to ruin Hamilton. For the low, low price of $1,000—paid in installments—he’d keep his mouth shut.
Why the James Reynolds Letter to Hamilton Changed Everything
You have to understand the political climate of the 1790s. The Federalists and the Democratic-Republicans hated each other. Like, truly loathed each other. Thomas Jefferson and James Madison were looking for any excuse to take Hamilton down. They thought he was a monarchist. They thought he was corruptly using Treasury funds to speculate on government bonds.
When James Reynolds was eventually arrested for a different scheme involving unpaid back pay for Revolutionary War veterans, he tried to trade his knowledge of Hamilton for his freedom. He told investigators—including future president James Monroe—that Hamilton had been using him to engage in illegal financial speculation.
📖 Related: Kate Middleton Astro Chart Explained: Why She Was Born for the Crown
This is where the James Reynolds letter to Hamilton becomes the smoking gun.
When Monroe and his colleagues confronted Hamilton with the receipts of the payments he had made to Reynolds, Hamilton had a choice. He could admit to a financial crime (treasonous for a Treasury Secretary) or admit to an affair (socially ruinous but technically legal).
He chose the affair.
The Content of the Blackmail
James Reynolds wasn't a master prose stylist. His letters are often frantic and poorly spelled, but they are effective. In one letter, he wrote:
"I have not sleeped a wink this night... I find that My happiness is banished from me forever."
It’s almost funny if it weren’t so destructive. He would alternate between playing the victim and being the aggressive extortionist. He even encouraged Hamilton to keep seeing Maria so he could keep the payments coming. Think about that. He was essentially pimping out his wife to the man running the nation's economy.
👉 See also: Ainsley Earhardt in Bikini: Why Fans Are Actually Searching for It
Hamilton kept every single one of these letters. Every. Single. One. He was obsessed with documentation. He believed that if he could show the timeline of the payments matched the timeline of the affair, he could prove he wasn't stealing from the government.
The Reynolds Pamphlet: A Self-Inflicted Wound
Fast forward to 1797. The rumors started leaking. A journalist named James Callender—who was essentially the 18th-century version of a tabloid hitman—published the allegations of Hamilton's corruption.
Hamilton went nuclear.
Instead of staying quiet or issuing a simple denial, he wrote the "Observations on Certain Documents," better known as the Reynolds Pamphlet. It was nearly 100 pages long. In it, he printed the James Reynolds letter to Hamilton and Maria’s letters too. He bared his soul and his bedroom habits to the entire world.
He thought he was being honorable. He thought that by proving he was just an adulterer and not a thief, he would save his political legacy. He was wrong.
The public didn't say, "Oh, thank goodness, he's just cheating on his wife!" They were horrified. His wife, Eliza, was humiliated. His political career was effectively dead. He would never hold high office again.
✨ Don't miss: Why the Jordan Is My Lawyer Bikini Still Breaks the Internet
Examining the Authenticity
Some historians, like Julian Boyd, have questioned if the whole thing was a cover-up for actual financial crimes. The theory goes that Maria and James Reynolds were just pawns Hamilton used to explain away mysterious "speculation" payments.
Honestly? Most modern historians don't buy that. The letters from Maria Reynolds feel too raw, too specific. And James Reynolds was exactly the kind of small-time grifter who would stumble into a goldmine and squeeze it until it broke. The James Reynolds letter to Hamilton exists as physical evidence of a man who was brilliant at math but terrible at human nature.
Key Takeaways from the Correspondence
- Financial extortion: James Reynolds eventually took over $1,300 from Hamilton. That's a massive sum for the time—equivalent to tens of thousands of dollars today.
- The "Invite": Reynolds actually invited Hamilton to continue the affair in writing, proving he was complicit.
- The Paper Trail: Hamilton’s insistence on saving these letters is what ultimately allowed the scandal to be reconstructed by historians centuries later.
How to View the Letters Today
If you want to see the real deal, many of these documents are held in the Library of Congress. Reading the transcriptions is a trip. You see a man like Hamilton, who wrote the foundational documents of the U.S. government, groveling and negotiating with a criminal.
It reminds us that the "Founding Fathers" weren't statues. They were people. They were flawed, they were impulsive, and they made massive mistakes. The James Reynolds letter to Hamilton serves as a permanent reminder that even the smartest person in the room can be undone by a moment of weakness and a very poorly managed secret.
What You Should Do Next
If you’re interested in the intersection of early American politics and personal scandal, don't just take the musical's word for it.
- Read the Reynolds Pamphlet: You can find the full text online at the National Archives (Founders Online). It’s long, but the introduction alone is a masterclass in "too much information."
- Visit the Grange: If you’re in New York, visit Hamilton’s home, The Grange. It gives a sense of the life he was trying to protect—and nearly lost.
- Study the 1790s Financial Crisis: Look into the "Panic of 1792." It provides the necessary context for why people were so suspicious of Hamilton’s finances in the first place.
The story didn't end with the letters. It ended with a duel in Weehawken years later, but the seeds of Hamilton's decline were sown the moment he replied to James Reynolds. Information was his weapon, but in this case, the pen was a double-edged sword that he accidentally ran himself through.