Angelica Schuyler Church, the charming Revolutionary era socialite, had her fair share of admirers, but none may be more intriguing than walking, talking, and writing contradiction in a greatcoat, Thomas Jefferson. While the third President of the United States had a reputation for solemnity after the early death of his wife, Angelica, a married woman herself, became the subject of Jeffersons letters and attention. Did the flirtatious exchanges between the two hint at something more, or was it simply the 18th-century equivalent of breadcrumbing?Angelicas Many LovesMiniature believed to be of Angelica Schuyler Church, by Samuel Shelley, 18th century. Source: PicrylAs depicted in the Broadway smash Hamilton, Angelica Schuyler was no stranger to male attention. Known for her cutting wit, beauty, and intellect, she corresponded with many of the Founding Fathers, from George Washington to the worlds favorite fighting Frenchman Marquis de Lafayette. However, her most famous admirer might be Alexander Hamiltonher brother-in-lawthough historians heatedly debate whether this relationship was playful but platonic or something significantly more. Her letters, to both Hamilton and Jefferson, reveal a woman who could charm with ease.Angelica was romantically inclined, so much so that her marriage started off with a bang that shocked her wealthy and well-connected family. Angelica eloped with John Barker Church, a British businessman and man on the run. Hed fled England after a duel (he literally shot a man and ranhe would also go on to make duels a throughline in Angelicas life). Despite his scandals, Angelica became famous for something far more gossipworthy: flirting. In this, as in many other areas, Angelica had a desire for the finer things. She only bestowed her interest on the most powerful men of the time.Letter from Angelica to Jefferson, July 21, 1788. Source: Get ArchiveMrs. Schuyler Churchs platform was Europes elite salons and Americas glittering New York ballrooms. As biographer Ron Chernow once pointed out, Angelicas connection with Hamilton was so intense that some of their contemporaries assumed they were lovers. Yet, Hamilton was not the only statesman caught in Angelicas web of charm. She also exchanged playful correspondence with Thomas Jefferson, who at one point all but begged her to join him on a leisurely trip to America. Six months after they met, Jefferson proposed (in true Jefferson fashion) that they negotiate her visit as if he were trying to clinch an international trade deal. Angelica didnt take him up on his offer.In a time when women were expected to remain behind the scenes, Angelica Schuyler Church refused to stand quietly by the men in her life. Whether she truly had affairs or just knew how to write a saucy love letter, one things for sureAngelicas pen was a force to be reckoned with.Both Knew Alexander HamiltonAlexander Hamilton, by Charles Shirreff, c. 1790. Source: PicrylIt is impossible to talk about Angelica and Jefferson without acknowledging the elephant in the roomoverachiever Alexander Hamilton. Not only was he married to Angelicas beloved sister, Eliza, but he was also one of Jeffersons most bitter political enemies.Angelica Schuyler and Thomas Jefferson both had front-row seats to the Alexander Hamilton Showand lets just say, the reviews were vastly different. On the one hand, Angelica was, like many women of the time, captivated by the handsome, well-spoken man. Hamilton was the 18th-century version of a modern-day heartthrob. His aura was less powdered wig and more troubled genius with a great jawline. Even his contemporaries described him as the youngest, best-looking, most controversial, and arguably the most brilliant of the major founders.Whether or not Angelica and Hamilton were ever more than dedicated friends has been the subject of many loud scholarly debates. Some argue that their relationship was purely platonic, driven by mutual respect and affection. If you write to someone saying you, seldom write to a lady without fancying the relation of lover and mistress, as Hamilton did in a missive to Angelica, youre either angling for a scandal or youve got the flirt game on lockdown. Meanwhile, Angelicas response to Hamiltons charm was equally flirtatious. In a letter to Hamiltons wife (yes, that Eliza), she joked that if her sister was as generous as the old Romans, shed lend her husband out for a bit. How Eliza felt about this muddle of a relationship has never been proven by documentation or a primary source.Eliza Hamilton, c. 1795. Source: PicrylOn the other side of this Hamilton-loving coin, theres Thomas Jefferson. The two mens dynamic was more clenched teeth and thinly veiled rage. They started out on vaguely cordial terms when they were both appointed to Washingtons cabinetHamilton as the Treasury Secretary and Jefferson as Secretary of Statebut things quickly turned sour. While Hamilton was all about building a strong, centralized government, Jefferson had a very different vision of America. He envisioned an agrarian utopia where noble farmers toiled in the sun, free from the clutches of big government, corporate greed, or monarchists.Quickly Jefferson became Hamiltons arch-nemesis. He organized an entire political partythe Republican Partyto make Hamiltons every move a bureaucratic nightmare. Jefferson suspected that Hamilton harbored secret plans to reinstate the monarchy and make himself king, something he didnt mind sharing with their fellow movers and shakers. While Hamilton was busy winning over the hearts of the Schuyler sisters, Jefferson was crafting bitter manifestos about corrupt, money-loving Federalists plotting behind closed doors.In the end, Angelica and Jefferson both experienced the Hamilton effectbut in very different ways. For Angelica, he was the dashing intellectual she could banter with, someone who would make her pulse race just a little faster. For Jefferson, Hamilton was more like a personal nemesis in a political cartoon: a larger-than-life character who seemed determined to ruin his idyllic pastoral vision for America. These men had one thing in commonthey found themselves waiting on Mrs. Schuyler-Churchs next letter.What Their Letters SayLetter from Angelica, 1804. Source: New York Public LibraryJeffersons letters to Angelica are filled with affectionate musings, frequently bordering on flirtation. In one, he writes about the sadness he felt after she left Paris, comparing the sunlight to an unwelcome guest during his loneliness. While Jefferson often wrote intimately to women, the tone of his letters to Angelica shows a man deeply attached to her, yet with an awareness of her marriage. It is unknowable if they ever acted on the sentiments in their letters, but the letters themselves tell modern minds about their deep and decades-long affection.One gem from Jefferson to Angelica says: The morning you left us, all was wrong, even the sunshine was provoking, with which I never quarreled before. Jefferson writes that mourning her departure, he quite literally hopped upon his horse and rode off in the direction shed gone, presumably casting longing glances at the horizon.Angelica and Jeffersons friendship was deepened by the fact that their families were quite intertwined. Jeffersons daughter, Martha, and Angelicas son, Philip, became fast friends while they were all in France. Angelicas daughter even stayed with the Jeffersons for a time. What an interesting household this must have made; Martha and Thomas daughters, Angelicas own child with John Barker Church, and a young Sally Hemmings, who would go on to give birth to at least three of Thomass future children.Daughters, by C.W. Eckersberg, 1820. Source: Raw PixelIn August 1788, he boldly invited Angelica to join him in America, proposing a kind of rendezvous that sounds more suited to a lovers getaway than a diplomatic mission. The letter lays out the flirtation, saying, Think of it, my friend, and let us begin a negotiation on the subject. You shall find in me all the spirit of accommodationYet for all the innuendo, there was something else happening in these lettersa mutual admiration for the revolutionary ideals of the time. Angelica wasnt just some charming figure in a pretty gownshe was actively involved in the political landscape, dabbling in espionage and intrigue. When she pitched in to organize a plot to free the Marquis de Lafayette from an Austrian prison, Jefferson must have been impressed.By the 1790s, Jeffersons letters still carried that warm undercurrent of affection, even while he was locking horns with Angelicas brother-in-law, Alexander Hamilton. It is a testament to their friendship that despite all the political drama, Angelica kept corresponding with Jeffersondodging his invitations to America but holding onto their connection all the same. Jefferson might have been a vice president by then, but to Angelica, he was still that sentimental man who couldnt stand the sunshine when she was gone.How History Remembers ThemRemembrance Statue, The Founders of the Daughters of the Revolution. Source: Wikimedia CommonsAngelica Schuyler remains celebrated for her intelligence and grace, while Jeffersons complex relationships with women continue to be a source of speculation. Whether or not their relationship was romantic, Angelica Schuyler and Thomas Jefferson certainly left an impression on each other, and on history.Angelica Schuyler Church may not have achieved household name recognition until Hamilton gave her a few unforgettable solos, but she was making waves long before Lin-Manuel Miranda brought her sass and brilliance into the spotlight. It is a shame her fame today tends to focus on the men she was tied to. Angelica was a renegade, navigating a world that did not quite know what to do with a woman who was both sharp as a tack and unafraid to get her hands dirty. It was because of her patronage that many male painters were able to fund their art.In a letter from Thomas Jefferson, he waxes poetic about Angelicas wit and charm: The urn is well worth acceptance, my dear Madam, on its own account but it is more flattering to me to accept it on account of the giver. He goes on to say, I am with you always in spirit: be you with me sometimes. That is 18th-century code for, I really wish I could hang out with you more.Angelicas death in 1814 didnt end her influence. Though her exact grave remains a bit of a mystery, her marker stands at the Livingston Family vault in the Trinity Churchyard, right where tourists flock to visit her more famous in-laws, Alexander and Eliza Hamilton.Thomas Jefferson, presidential portrait, by Rembrandt Peale, 1801. Source: The White HouseIt appears that brilliance and a streak of independence runs in the Schuyler blood. Take Angelicas descendant Marian Cruger Coffin, for example. Born in 1876, Marian became one of Americas pioneering landscape architects, designing gardens for an East Coast elite clientele. At a time when women were expected to pick flowers rather than design where they bloomed, Marian broke the mold. She studied at MIT, one of just four women in her field at the time, and went on to craft some of the most famous gardens in the country. Angelica would have been proud.Thomas Jefferson, a man who was just as obsessed with his legacy as he was with writing flowery letters, was no stranger to self-promotion. In his final years, he meticulously shaped how future generations would remember him, going so far as to draft his own epitaph. In classic Jefferson fashion, he highlighted his authorship of the Declaration of Independence and his founding of the University of Virginia, purposefully omitting his role as president. Perhaps he preferred to be remembered for writing the Declaration of Independence rather than for governing a nascent nation with messy politics. To Jefferson, education, and liberty were the cornerstones of his legacy. Despite his heavy-handed propaganda, the critics came for him, questioning his commitment to individual freedom while conveniently ignoring his role as a slaveholder.Jeffersons descendants have been making their own waves in the modern era. Shannon LaNier, his DNA-proven sixth great-grandson through Sally Hemings, has taken the complicated legacy of Jefferson head-on. LaNier, now an author and TV host, has been vocal about how he hopes his familys history can play a role in healing the divisions in the United States. He continues to engage in conversations about race, identity, and the complexities of Americas past, navigating the mixed legacy Jefferson left behind.Thomas Jefferson Statue at University of Virginia, by Kipp Teague. Source: FlickrAngelica Schuyler and Thomas Jefferson were not simply characters in the background of revolutionary history. While Jefferson has been etched into marble and textbooks, Angelica, for all her social connections, intelligence, and audacity, has only recently started getting the credit she deserves. The small town of Angelica, New York, named in her honor by her son, might be far from the glamorous places she once called home, but it stands as a testament to the kind of woman she wasone who left her mark, whether or not history was paying attention. It might be time to give Angelica a bit more of the spotlight and recognize her as the feminine influencer she was. After all, a woman who could charm Jefferson and offer casual political advice to Hamilton is not someone who should be reduced to a footnote in someone elses story.