The Washington PostDemocracy Dies in Darkness

America’s first ‘hush money’ scandal: Alexander Hamilton’s torrid affair with Maria Reynolds

(Library of Congress)
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On Dec. 15, 1792, James Monroe and two other members of Congress stepped through Alexander Hamilton’s door, ready to torpedo the powerful treasury secretary’s career.

They did not realize the curtain was about to rise on the nation’s first major political sex scandal.

The three men believed they had uncovered a financial scam linking Hamilton to a pair of shabby fraudsters, James Reynolds and Jacob Clingman. Notes in Hamilton’s own handwriting to Reynolds and his wife seemed to back up the allegation. Monroe and the two others —  Rep. Frederick Muhlenberg of Pennsylvania and Rep. Abraham B. Venable of Virginia — had already drafted a letter to President George Washington outing the Cabinet member.

The house call was only a sign of respect before exposing Hamilton to the long knives of public scorn.

As Hamilton would later write, the three politicians “introduced the subject by observing to me that they had discovered a very improper connection between me and a Mr. Reynolds.” The treasury secretary, however, cut them short. They had it wrong, he explained. He was not involved in financial duplicity, but an extramarital affair with Reynolds’s wife, Maria.

The woman’s husband knew of the affair, forcing Hamilton — one of the most powerful figures in the fragile republic — to fork over hush money.

“Another man might have been brief or elliptical,” Ron Chernow wrote in his 2005 classic biography. “Instead, as if in need of some cathartic cleansing, Hamilton briefed them in agonizing detail. . . . It was as if Hamilton were both exonerating and flagellating himself at once.”

Realizing they were dealing with an affair of the heart, not the state, Monroe, Muhlenberg and Venable pledged to stay mum. The letter to Washington went unsent. But the affair would eventually explode into the public domain, marking the first high-profile sex scandal to rock the new nation’s political scene.

The scandal not only sank Hamilton’s larger political aspirations and inspired a song in Lin-Manuel Miranda’s blockbuster musical, but the payoffs also prefigure the current headlines.

On Sunday, porn star Stormy Daniels will sit down with Anderson Cooper on “60 Minutes.” She is expected to detail not only her alleged affair with President Trump but also efforts on the part of the real estate developer’s team to buy her silence with a $130,000 payment in conjunction with a “nondisclosure agreement.”

Hamilton’s “Reynolds Affair,” as it’s known, began in the summer of 1791 when the 23-year-old blond woman, Maria Reynolds, knocked on his door in Philadelphia in desperate need. As Reynolds explained, her husband had abandoned her and she was in need of financial help getting back to New York City. Hamilton, then 36 and by all accounts dashing, offered to bring money to Maria’s home. When he arrived, he was shown into the bedroom.

“Some conversation ensued from which it was quickly apparent that other than pecuniary consolation would be acceptable,” Hamilton later wrote.

Maria and Hamilton continued to meet, including at Hamilton’s own house when his wife, Eliza, and their children were visiting family in Albany. “It is baffling that Hamilton, having worked to achieve a spotless reputation as treasury secretary, did not see that he was now courting danger and would be susceptible to blackmail,” Chernow says in his book.

James Reynolds eventually reappeared on the scene, confronting Hamilton about his relationship with his wife. Initially appearing outraged, the husband then encouraged Hamilton to continue the affair. As Hamilton wrote, he “invites me to renew my visits to his wife.”

“Its true its in your power to do a great deal for me, but its out of your power to do any thing that will Restore to me my Happiness again for if you should give me all you possess would not do it,” Reynolds said in a note to Hamilton. “I have this preposial to make to you. give me the Sum Of thousand dollars and I will leve the town.”

That sum, $1,000 in hush money, is the equivalent of about $25,000 today.

Hamilton paid and continued to make amorous calls on Maria. Her husband continued to hit up the powerful government official for money after the encounters, $30 or $40 sums Reynolds cast as loans. He even gave Hamilton receipts. According to Chernow, both Maria and her husband were probably working together on the extortion plot.

By the summer of 1792, Hamilton cut off the affair. But that November, Reynolds found himself in a Philadelphia jail cell. Along with a partner, Jacob Clingman, he was charged with defrauding the U.S. government. The two men were accused of posing as the executors of a Revolutionary War veteran to claim $400 in back pay due to him.

While free on bail, Clingman tried to secure the help of his former employer, Muhlenberg. The accused scammer sparked the politician’s curiosity.

Muhlenberg wrote later: “Clingman, unasked, frequently dropped hints to me that Reynolds had it in his power, very materially, to injure the secretary of the treasury and that Reynolds knew several very improper transactions of his.”

Muhlenberg brought this information to Monroe and Venable. The trio interviewed both Maria and her husband about the connection with Hamilton. The couple declined to give specifics on their relationship with the treasury secretary, but Maria provided the politicians with letters between her husband and Hamilton. She claimed she had burned many others.

The three men were convinced Reynolds was involved in some official misconduct with Hamilton. Free on bail, Reynolds fled — further confirming their suspicions. On Dec. 15, they decided to confront the Cabinet official.

Hamilton instead shocked Monroe, Muhlenberg and Venable with his story about the affair. He showed — and allowed them to copy — letters from both Maria and James Reynolds as evidence.

“The small delegation seemed satisfied with Hamilton’s chronicle, if not a little flustered by the awkward situation,” Chernow wrote. “They apologized for having invaded his privacy.”

They also pledged to keep the matter private. Maria Reynolds eventually sued her husband for a divorce. The attorney she hired to represent her was Aaron Burr.

The affair eventually went public in 1797 as part of a complex political chess match between Hamilton and his enemies in Thomas Jefferson’s Republican Party.

That year, a pro-Jefferson writer named James Callender published a series of pamphlets, “The History of the United States for 1796.” The text revived accusations that Hamilton, now out of the Cabinet, had engaged in official misconduct with Reynolds and Clingman.

As proof, Callender published the same letters Hamilton had shown Monroe, Muhlenberg and Venable in 1792. The pamphlet suggested the romance between Maria and Hamilton was a cover story for shady financial dealings.

Hamilton was in a tight spot. Five years earlier, cornered with the allegations by Monroe and the others, he had opted for disarming honesty. Now, with the Reynolds affair again circulating, he did the same on the public stage with a preemptive strike that would allow him, as the phrase now goes, to put his own spin on everything.

Hamilton published a 95-page pamphlet. For 37 pages, he confessed and outlined the affair and extortion; the remaining 58 pages were supplemental letters and affidavits proving his case.

The song, “The Reynolds Pamphlet” in Lin-Manuel Miranda’s musical opens with Jefferson, Madison and Angelica Schuyler (Hamilton’s sister-in-law) exclaiming “Have you read this?”

Aaron Burr, Jefferson and Madison then describe the horror revealed: “Alexander Hamilton had a torrid affair. And he wrote it down right there.”

The pamphlet’s actual words are something less than “torrid”-sounding to modern eyes.

“The charge against me is a connection with one James Reynolds for purposes of improper pecuniary speculation,” Hamilton wrote. “My real crime is an amorous connection with his wife, for a considerable time with his privity and connivance, if not originally brought on by a combination between the husband and wife with the design to extort money from me.”

The confession may have cleared Hamilton of official misconduct, but it also smeared his name and embarrassed his family. Both Hamilton and his wife, Eliza, believed that James Monroe — a close friend of Hamilton’s archrival Thomas Jefferson — had provided the letters to Callender.

Hamilton eventually confronted Monroe at his home in New York.

“I will meet you like a gentleman,” Hamilton said, using the language of a duel.

“I am ready, get your pistols,” Monroe shot back.

The two were eventually talked down from a violent confrontation. The man responsible for defusing Hamilton’s anger was none other than Aaron Burr, the New York senator who would later kill Hamilton in his own duel in 1804.