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  • Mike Martinez

America's First Major Sex Scandal: Alexander Hamilton

My latest book project, tentatively titled Scoundrels: Political Scandals in American History, is a retrospective examination of infamous scandals in U.S. history. The book is under contract with my long-time publisher, Rowman & Littlefield. The manuscript is due in October 2020, with publication expected sometime in mid-2021. In this and subsequent blogs, I want to discuss the 26 representative scandals discussed in Scoundrels and what they tell us about American politics.

You read sentence that correctly: representative scandals. Alas, there are more than 26 scandals in the nation’s history, but I needed to limit the number lest the book become too big, unmanageable, and bloated to publish. The scandals are divided evenly—13 sex scandals and 13 financial corruption/abuse of power scandals.

The first chapter highlights a sex scandal involving a revered Founding Father, Alexander Hamilton, who was serving as secretary of the treasury in June 1791 when a comely twenty-three old woman arrived at his home in Philadelphia and asked to speak with him privately. He might have ignored the entreaties of a stranger who appeared, unannounced, at his door. After all, he was a busy man handling weighty affairs of state. Nonetheless, when he was informed that a female visitor had come calling, he stepped away from his duties and “attended to her in a room apart from the family.”

As Hamilton later described the encounter, she told a tale of woe with “a seeming air of affliction” about a husband who had treated her cruelly and deserted her, leaving her financially destitute. She appealed to Hamilton, “knowing that I was a citizen of New York.” Apparently believing him to be a generous man, she “had taken the liberty to apply to my humanity for assistance.” In short, she needed a loan.

The petitioner’s name was Maria Reynolds. Little is known of her background or early life. She was born Mary Lewis in Dutchess County, New York, in 1768. At age 15, she married James Reynolds. She gave birth to a daughter, Susan, two years later. She also began calling herself “Maria.” Beyond not, few facts can be confirmed.

Although she wore the face of an ingénue, beneath the carefully constructed façade, Maria Reynolds was a conniving, manipulative, blackmailing hustler—a woman of “easy virtue,” as wags euphemistically described an adulteress in that age. Almost certainly she presented herself to Hamilton in the hopes of luring him into a sexual relationship that would lead to blackmail.

If his wife was the proverbial Jezebel, James Reynolds was her Ahab. He was no king, of course, but he aspired to be a man of means. By most accounts, James was a well-known liar and cheat. He had defrauded Continental soldiers and their widows and orphans of back pay in a well-known escapade. Hamilton may have known of the man’s sordid reputation. If so, his wife’s story rang true.

Hamilton did not have any funds on the premises, but he agreed to visit his bank and bring money to her later in the day. This was an extraordinary promise to make to someone he had just met. Had anyone other than an attractive young woman appeared at his house, he probably would have sent the petitioner packing in short order.

Maria told him the address of her boarding house where she was staying. True to his word, he appeared that evening at 154 South Fourth Street with a $30 bank bill, equivalent to $400 today. When he arrived at the boarding house, according to Hamilton’s account, “I inquired for Mrs. Reynolds and was shown upstairs, at the head of which she met me and conducted me into a bedroom.” He handed her the bank bill, and they spoke briefly. Standing in this young woman’s bedroom after fulfilling her request, the incident came to a predictable conclusion. Hamilton recognized that “it was quickly apparent that other than pecuniary consolation would be acceptable.” They fell into her bed.

“After this,” Hamilton admitted later, “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.” The on-again, off-again affair lasted approximately a year, whenever Hamilton could slip away from his wife.

As the affair continued, Maria intimated to Hamilton that her husband had profited from speculation in government securities and had even used insider information from a source in the Treasury Department. When he heard that someone in the department might compromise Hamilton’s good work, he sent for James Reynolds. It is ironic that in fearing for the reputation of the Treasury Department owing to the work of a scoundrel, Hamilton failed to see, or he ignored, the strong possibility that he himself was acting as a scoundrel.

James Reynolds appeared before him and claimed that William Duer was the source of his information. Duer had already left the department at the time the disclosure reputedly occurred, and so Hamilton decided that “this discovery, if it had been true, was not very important—yet it was the interest of my passions to appear to set value to it, and to continue the expectation of friendship and good offices.” The remark is telling. Hamilton recognized that James Reynolds might be lying, and yet the affair with Maria remained “the interest of my passions.”

On the surface, this initial meeting was amicable, but danger lurked for Hamilton. He must have known that he had left himself vulnerable to blackmail. If he did not know it, he would soon learn. During the initial meeting, however, the parties acted as though they were the best of friends. Maria told her husband that Hamilton had aided her when she needed it. James feigned gratitude. The only overtly sour note came at the conclusion. According to Hamilton, “Mr. Reynolds told me he was going to Virginia, and on his return would point out something in which I could serve him. I do not know but he said something about employment in a public office.” No firm offers were tendered.

Reynolds returned from his travels and, as he had promised, he asked for a job in the Treasury Department. In the man’s absence, Hamilton had discovered the sort of fellow he was, assuming he had not known beforehand. The secretary refused, explaining that no openings existed in his office.

Reynolds was dissatisfied with this excuse. He believed that during their initial meeting, Hamilton had agreed to provide a job. “The situation with the wife would naturally incline me to conciliate this man,” Hamilton candidly admitted. “It is possible I may have uttered vague expressions which ratified expectation, but the more I learned of the person, the more inadmissible his employment in a public office became.”

He now knew that he faced stark choices. During the fall of 1791, Hamilton attempted to break off contact with Maria. She wrote him copious letters filled with misspelling and atrocious grammar, but her intentions were plain enough. She loved Hamilton. She could not bear to part with him. The wisest course of action would have been to cease all contact, but he seemed unwilling or unable to cut ties with the Reynolds duo. Hamilton remained locked in the destructive relationship. He labeled his vacillation between breaking off the affair and continuing the visits a “state of irresolution.”

Matters came to a head on Thursday, December 15, 1791. On that date, Hamilton received letters from both Maria and James Reynolds. The former wrote, she said, to warn that her husband had discovered their sexual affair and might blackmail the secretary. “It was a matter of doubt with me whether there had been really a discovery by accident, or whether the time for the catastrophe of the plot was arrived,” Hamilton later mused.

In his letter, James Reynolds played the role of the affronted husband, outraged that Hamilton had “acted the part of the most Cruelist man in existence,” and, in so doing, “you have made my whole family miserable.” Reynold promised that “I am [determined] to have satisfaction.” Recognizing that he could not ignore the implied threat, Hamilton summoned the aggrieved man to his office that afternoon.

Reynolds arrived to find a wary adversary. Hamilton could not be sure how much that Reynolds knew, or whether the man possessed incriminating evidence. Resolving not to worsen an already terrible situation, Hamilton listened as James changed his demands from seeking employment to requesting a “loan.” During a second meeting a few days later, Reynolds said that he would consider $1,000 an adequate sum to restore his “wounded honor.” Hamilton agreed, paying one installment on December 22, and a second on January 3. Finally coming to his senses, he sought to end the affair.

James Reynolds demonstrated his venality beyond any doubt, as if such a demonstration were needed, when he responded to Hamilton’s decision to terminate all contact with Maria. The wounded spouse, staggering from the blow to his pride and upset at the cruel man who had alienated his wife’s affection, suddenly wrote a letter to Hamilton explaining that Maria was inconsolable. She missed Hamilton so much that she had broken down. Out of a selfless concern for her welfare, James invited Hamilton to consider Maria a “friend” and renew his visits.

Having exercised a modicum of wise judgment, Hamilton threw caution to the wind and continued seeing Maria long past the point when he should have walked away. The sexual obsession would not be denied. Not surprisingly, James Reynolds remained involved, expressing concern for his wife, and seeking additional payments from her lover. He also ran hot and cold, occasionally telling Hamilton to stay away from his wife, and other times encouraging their visits. By the time all was said and done, the pimp-turned-blackmailer had extorted $1,300, a princely amount.

What started as a private failing of a public man became a sensational scandal owing to a confluence of events in 1792. It began with Jacob Clingman, a former clerk to Frederick Muhlenberg, speaker of the Pennsylvania House of Representatives. Clingman knew James and Maria Reynolds, and he was visiting them when he spied Alexander Hamilton leaving the premises. The odd spectacle of seeing most of the nation’s most famous men at the Reynolds’ residence occurred again several days later, when Clingman saw Hamilton enter a room, pass a message to Maria, and hastily leave. When Clingman asked what was going on, Maria told him that Hamilton had paid her husband more than $1,100. James said that Hamilton had given him money for speculation. Initially skeptical, Clingman changed his mind when he accompanied James Reynolds on a visit to see Hamilton. While Clingman waited outside, Reynolds went in to see Hamilton, and he emerged from the meeting with $100.

A political opponent of the treasury secretary, Clingman was convinced that Hamilton was skimming money from the U.S. Treasury to engage in financial speculation, an illegal breach of the public trust. The extravagant payments to James Reynolds only confirmed his suspicions. Still, he sat on his suspicions until he was arrested, along with James Reynolds, for defrauding the U.S. government after posing as executors of a deceased war veteran’s estate to procure payment for money owed to the man for his military service.

Because the Treasury Department prosecuted the case, Reynolds believed that Hamilton had engineered the charges to ensure his silence. Reynolds and Clingman were hauled off to jail. Reynolds wrote to Hamilton twice asking for assistance. When he did not receive a response, he loudly complained to anyone who would listen that he possessed damaging information and could “make disclosures injurious to the character of some head of a department.” When Hamilton learned of the threats, he instructed his men to keep Reynolds locked away until such time as the man was prosecuted.

Clingman, however, secured his release on bail. He immediately ran to his former boss, Frederick Muhlenberg, then serving as a United States congressman. After hearing about the possibility of financial misconduct, Muhlenberg agreed to assist Clingman, although he carefully distanced himself from the “scoundrel” James Reynolds. Accompanied by New York Senator Aaron Burr, Muhlenberg met with Hamilton and arranged a compromise. Clingman agreed to refund the stolen money, turn over a purloined list of soldiers who were owed money by the government, and provide the name of the Treasury Department official who had leaked the list. In exchange, the Treasury Department would drop the charges against Reynolds and Clingman.

Rather than expressing his gratitude to Hamilton for arranging a compromise, Clingman confided in Muhlenberg that the secretary had engaged in improper speculation with Reynolds, suggesting that Treasury Department funds were used to enrich Hamilton and his friends. Muhlenberg was initially skeptical, but James Reynolds insisted that he possessed information that would “hang” Hamilton. Muhlenberg eventually decided that he could not keep the information to himself. The nature of the claims would have to be investigated.

Muhlenberg approached two Virginia men, Senator James Monroe, and Congressman Abraham B. Venable, and told them of his suspicions. Clingman had provided Muhlenberg with unsigned notes from Hamilton to James Reynolds, which lent an air of authenticity to the claims. The Virginians were Hamilton’s political adversaries and anxious to expose any information that would present the treasury secretary in a poor light. They hastened to James Reynolds’s jail cell. The prisoner was as circumspect as ever, but he alluded to the misconduct of a person of high office. Monroe and Venable knew that Reynolds was speaking of Hamilton, but Reynolds would not say his name.

These behind-the-scenes machinations among Clingman, Muhlenberg, Monroe, and Venable revolved around a muddled claim of financial impropriety. No one in the circle yet knew of the sexual liaison at the heart of the mystery. Still unsure of what they were investigating, Muhlenberg and Monroe visited Maria Reynolds on the evening of December 12, 1792. She furnished them with additional information about payments, but she did not mention an affair. She had confided in Pennsylvania Governor Thomas Mifflin about the Hamilton trysts, but she chose not to inform the members of Congress now delving into the matter.

In the meantime, James Reynolds, newly released from prison, ran off to God-knows-where, leaving the three members of Congress more suspicious than ever that Hamilton must be engaged in a massive financial scandal. The trio drafted a letter to President George Washington, but they needed to perform one last act of due diligence. They requested an audience with Hamilton to outline what they knew and seek his response.

On December 15, 1792, Messrs. Muhlenberg, Monroe, and Venable filed into Hamilton’s office and confronted him about the “very improper connection” with James Reynolds. Angered by the accusation, Hamilton demanded to know plainly what they were insinuating. The men were taken aback. They assured the secretary that they had no concrete evidence, but they felt duty-bound to inform the president of what they did know. They produced the handwritten notes from Hamilton to Reynolds, which changed Hamilton’s demeanor instantly. His anger evaporated. Requesting time to prepare his case, he asked the men to join him at his home that evening and he would lay bare all the facts necessary to explain his connection with James Reynolds.

The men appeared at Hamilton’s door at the allotted time expecting to hear a defense of his financial transactions. They were stunned at what he told them. Having decided that he should provide all the facts in excruciating detail, Hamilton laid bare the circumstances of the affair from beginning to end. He produced letters to show the sequence of events. It was clear that his interlocutors were uncomfortable by this running narrative, but Hamilton was determined to supply an exhaustive explanation for his conduct.

It is possible that the affair never occurred, and the lengthy narrative was an elaborate ruse to disguise financial improprieties. If that was the case, Hamilton gave a virtuoso performance that evening. His audience never doubted him for a moment. The level of detail and Hamilton’s obvious embarrassment at having been duped by the unscrupulous couple convinced Muhlenberg, Monroe, and Venable that a scandal involving marital infidelity was a private matter. They departed with promises to keep the matter confidential. They never sent the draft letter to Washington.

Regardless of their politics, Muhlenberg and Venable were sympathetic to Hamilton. James Monroe, however, was too much of a partisan to allow such matters to remain buried indefinitely. Hamilton subsequently asked for copies of the correspondence that the three men had shown him. They readily agreed, but they also retained copies. One set wound up in the hands of John Beckley, clerk of the House of Representatives and a devoted friend of Hamilton’s archenemy, Thomas Jefferson. Monroe may have shared copies with Jefferson as well.

For four-and-a-half years, despite “dark whispers” that circulated among his Republican opponents, Hamilton conducted his public business without having to answer for the Reynolds affair. He left the Treasury Department in 1795. Always spoken of as a potential presidential candidate, he never formally pursued the ultimate prize, although doubtless he coveted the position. Perhaps he knew the affair would come to light if he threw his hat into the ring.

Enter one James Thomson Callender, a Scottish-born political operative who had fashioned himself into a scandalmonger. Callender had carved out a career as a purveyor of rumor and innuendo in service of political causes, mostly on behalf of Jefferson’s Republican Party. In this case, Callender advertised a publication titled The History of the United States for 1796, which promised to expose information about the Hamilton-Reynolds episode of 1791-92. The gist of the argument was that when he was secretary of the treasury, Hamilton had engaged in official misconduct, and the payments to James Reynolds were proof. As part of his string of allegations, Callender referred to Hamilton’s adultery.

The timing of the Callender missive was not accidental. The previous year, Hamilton had alluded to improprieties in Jefferson’s private life, a not-so-subtle reference to rumors about the master of Monticello and his slave, Sally Hemings. Callender was often in the Republicans’ employ, and so his revelations may have been payback for Hamilton’s indelicate remarks about the Sage of Monticello.

Hamilton was furious when he read The History of the United States for 1796 and saw copies of the documents that Muhlenberg, Monroe, and Venable had had in their possession in December 1792. After sifting through the documents, Hamilton understood that he had been betrayed. He thought he knew the source of the leak, too: James Monroe. He and Hamilton were political enemies, and it was certainly plausible to assume that Monroe had provided the documents to Callender. When Hamilton confronted Monroe, however, the latter denied his involvement. The two men exchanged words, and they came perilously close to engaging in a duel. Ironically, it was only through the intervention of Aaron Burr—who killed Hamilton in a duel seven years later—that the potential combatants agreed to stand down

Hamilton put pen to paper and produced a lengthy essay thoroughly refuting the charges. Although he might have been brief in his defense, Hamilton decided to lay out his case in the full context of the controversy rather than allow his detractors to misinterpret his words. The result was one of the most astonishing public letters ever written by an American politician. Published on August 25, 1797, and titled Observations on Certain Documents Contained in No. V & VI of “The History of the United States for the Year 1796,” In which the Charge of Speculation Against Alexander Hamilton, Late Secretary of the Treasury, is Fully Refuted, Written by Himself, it is usually known as The Reynolds Pamphlet. Just as he had done with Muhlenberg, Monroe, and Venable years earlier, Hamilton exhaustively reviewed the facts, providing copies of letters and referring to his critics’ charges head-on. The crux of his argument was that the scandal was sexual, not financial: “The charge against me is a connection with one James Reynolds for purposes of improper pecuniary speculation. 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.”

In one sense, The Reynolds Pamphlet achieved Hamilton’s goal. He ably defended his public reputation by sacrificing his private life. His argument—yes, I misbehaved by straying from my marriage, but I never abused my public office by stealing from the Treasury—was strong and convincing. In laying out such unflattering information about himself, complete with copies of pertinent correspondence, he left little room for his critics to add much to the story. His candor and willingness to confront the scandal without waffling or deflecting responsibility demonstrated his ability to make hard choices and persevere, come what may. Yet he also diminished his reputation immeasurably. Republicans chortled that the man long viewed as a low-class bastard from the West Indies had been revealed as the unprincipled Libertine they knew him to be. He humiliated his wife and family as well. Hamilton’s well-wishers remained adamantly at his side—George Washington sent him a warm letter with a gift of wine coolers—but he may have destroyed his chances to capture the presidency.

In virtually every tale of a powerful man engaging in risky behavior, critics shake their heads and ask, “what was he thinking?” Surely, Hamilton knew, or should have known, that the affair would become public. Great men with famous faces and an array of political enemies must realize that, sooner or later, sexual peccadilloes will become fodder for newspapers and political opponents. Yet time and again, these men engage in affairs that damage their reputations, their family lives, their political careers, and their historical legacy. And so it was with Alexander Hamilton.

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