Alexander Hamilton Had a Steamy Affair, Then Told the World All About It

Modern politicians use a variety of PR strategies when caught with their proverbial pants down. Some of the more recent include denying any affair has taken place (Bill Clinton “did not have sex with that woman”), spinning a story of having gone off-the-grid on a long, solo trip (Mark Sanford was just recharging alone in “exotic” Buenos Aires, he swears), or attempting to deflect suspicion by claiming your married aide is the father of your pregnant mistress’s child (that one was a John Edwards special).

What these wandering eyes of power didn’t do is make the decision to come clean very publicly on every last detail of their indiscretions—including printing copies of their love letters—when rumors began to swirl. Only one man can claim that bold and, from the standpoint of any communications adviser ever, idiotic move: Alexander Hamilton.

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Hamilton was the subject of the first political sex scandal in American history. In a twin distinction, he has also served as the cautionary tale for anyone who has found themselves in the spotlight for a high-profile impropriety ever since. He wrote the first entry in the “What Not To Do” playbook.

Like so many of his philandering successors, Hamilton largely recovered from the scandal, but not without earning a permanent historical scar. Many historians believe that the Hamilton-Reynolds Affair, as the episode became known, squashed any chance he had at becoming president. And, to this day, his indiscretion is a key moment in every biography of the “Ten-Dollar Founding Father,” as the hit Broadway show Hamilton proves. An entire song is dedicated to the affair that ensured “well, he’s never gon’ be president now.”

The best part of Hamilton’s affair was its utterly absurd beginning. The infamous meeting occurred one day in the summer of 1791 when the then-Secretary of the Treasury was living in Philadelphia. By that time, he was 34 and married with four children. Accounts differ as to his family’s whereabouts that day. While many contend that Elizabeth (“Betsey”) Hamilton had already taken the kids to Albany to visit her family, Ron Chernow, who wrote the definitive biography on the Founding Father, suggests they may have still been at home.

For the sake of our story of romantic misadventure, and with no available weather records, we’re going to assume it was a sultry Pennsylvania day when 24-year-old Maria Reynolds came to the Hamilton residence with a request that was bizarre even by the standards of the time.

Reynolds was in a bad marriage. Her husband was a conman and abusive, and she claimed that he had also recently abandoned her. She was from a semi-prominent family in New York City, and she decided to appeal to a fellow New Yorker for financial help to travel back home. For whatever reason—he was busy, his wife was in the other room, he was feeling FOMO that he didn’t have plans for the evening—Hamilton told Maria he was willing to help her, but that exact moment wasn’t convenient (“which was the fact,” he later maintained). Could he, perchance, meet her that evening to settle the matter?

By Hamilton’s own self-published account in what became known as the Reynolds Pamphlet, he arrived at her rooming house later that night and “inquired for Mrs. Reynolds and was shown upstairs, at he head of which she met me and conducted me into a bedroom. I took the bill out of my pocket and gave it to her. Some conversation ensued from which it was quickly apparent that other than pecuniary consolation would be acceptable.”

Maybe Maria had designs on Hamilton from the beginning, as some said. Maybe she was in cahoots with her conniving husband or Hamilton’s enemies. Or maybe she was just a woman in need whose evening took a wild turn. Either way, it’s really something to imagine one of the architect’s of our great nation, one of the unparalleled geniuses in American history, not batting an eye when he found himself in a sequence of events that, by his own account, went a little something like “Hi, Mrs. Reynolds. I have money to help you get back home. Oh, you’re fine if I sleep with you, instead? Ok, let me put my cash away and I’ll meet you under the sheets.”

That one strange evening turned into a months-long affair. Needless to say, Mrs. Reynolds didn’t make it back to New York.

“After this, I had frequent meetings with her, most of them at my own house; Mrs. Hamilton with her children being absent on a visit to her father,” Hamilton wrote.

According to another biographer, Richard Brookhiser, during much of the time of the affair, Hamilton “wrote clumsily deceitful letters to Betsey, telling her how much he missed her, but that she should stay where she was. ‘I am so anxious for… your health that I am willing to make a great sacrifice…’”

Needless to say, the lovers were eventually discovered when Mr. Reynolds came back into the picture. Hamilton claimed in his account that Maria came to him seeking advice when her husband returned wanting to reconcile, and he told her to revive the marriage. But the epistolary record paints a different picture.

On Dec. 15, Maria sent a rushed letter to Hamilton, saying her husband had discovered the affair. “‘I have not tim to tell you the cause of my present troubles only that Mr. has rote you this morning and I know not wether you have got the letter or not and he has swore that If you do not answer It or If he dose not se or hear from you to day he will write Mrs. Hamilton.”

Two days later, Hamilton received the letter in question. James Reynolds claimed to be distraught, but he was willing to keep quiet and leave them to it if he was paid $1,000.

But things weren’t so simple as that. Reynolds was a conman, after all, and rather than being heartbroken by his wife’s infidelity, he saw an opportunity. The evidence is pretty clear that, by that point, he had coopted Maria into his scheme, if she wasn’t already involved.

Hamilton paid up, and the affair lasted through the fall, with many letters exchanged between the two lovers. Hamilton claimed that he wanted to break it off earlier and that he was beginning to have suspicions (the Secretary of the Treasury would continue to respond to smaller monetary requests that periodically arrived from Reynolds), but Maria’s “conduct, made it extremely difficult to disentangle myself.”

But he finally broke free, and that’s where the story might have ended.

Except that Reynolds was a conman through and through and, one year later, he was arrested for another scheme that involved defrauding the nascent American government out of pension money meant for Revolutionary War soldiers. He appealed to his high-powered “friend” for help, but this time, Hamilton refused to come to his aid. Pissed off, Reynolds approached several politicians with a story about being a victim of Hamilton’s corruption. The Secretary had not only forced Maria to be his lover, Reynolds said, but he was also involved in the pension scheme. He had Hamilton’s love letters to his wife to prove it.

When the group of political colleagues-cum-investigators approached Hamilton with the accusations, he was outraged, but mostly by the insinuation of financial impropriety. In an effort to clear his name, he came clean about the affair and the blackmail he had paid, but he proved that the money was all from his own pocket.

Once again, the sordid episode could have ended there. But Hamilton wasn’t so lucky.

It turns out, understanding the value of political opposition research is almost as old as America’s democratic project. James Monroe, who was among the investigators of the Hamilton affair, hadn’t destroyed the love letters Maria had turned over as he had promised. Instead, he sent a copy of the letters to Thomas Jefferson, Hamilton’s main political rival. (Hamilton would challenge Monroe to a duel for this betrayal, although both men were talked down before they took their positions.) Another copy was also made, possibly by a clerk working on the investigation.

In 1797, as the animosity between Jefferson and Hamilton heated up, the letters were published by a journalist who was firmly in Jefferson’s political camp. But even worse than the airing of romantic indiscretions was the revival of the accusations of financial malfeasance, of which Hamilton had already been cleared.

When Monroe didn’t jump to his defense quickly enough, Hamilton decided his only recourse was to assure the public that no financial misconduct had been committed by publishing a full account of the sordid details of his affair in the Reynolds Pamphlet. In the words of Lin-Manuel Miranda, “Alexander Hamilton had a torrid affair / And he wrote it down right there.”

“Thus has my desire to destroy this slander, completely, led me to a more copious and particular examination of it, than I am sure was necessary,” Hamilton wrote. “The bare perusal of the letters from Reynolds and his wife is sufficient to convince my greatest enemy that there is nothing worse in the affair than an irregular and indelicate amour.”

The Reynolds Pamphlet served its purpose. The former Secretary of the Treasury’s financial name was cleared, but, by giving the citizens of America a detailed romp of a read through his personal life, Hamilton curtailed his political prospects.

As the fallout from our famous modern political sex scandals proves, the truth usually does come out, and flimsy excuses and outrageous denials look downright ridiculous when the full story is told. But being the whistleblower on your own deep, dark secrets is another level of honesty altogether.

In the words of Javier Muñoz, who spoke with Vulture in 2015 about playing Hamilton in the famous musical: “Dude, WHY the Reynolds Pamphlet? What were you thinking? What were you thinking?”

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