America’s Polymath Pirate Queen: The Brief Wondrous Life of Theodosia Burr Alston

“If I could foresee that Theo would become a mere fashionable woman, with all the attendant frivolity and vacuity of mind, adorned with whatever grace and allurement, I would earnestly pray God to take her forewith hence. But I yet hope by, her, to convince the world what neither sex appears to believe—that women have souls.” – Aaron Burr to his wife (February 8, 1793)

“Never were hope brighter than mine. To look on the gloomy side would be the death of me.” – Theodosia Burr Alston to her father (June 21, 1808)

[Portrait of Theodosia Burr Alston, John Vanderlyn (1802). Aaron Burr was a patron and friend of Vanderlyn for many years; as you’ll see, many of the paintings of Theo and her father were done by him. When he was in Europe, Burr kept one of Theo’s portraits with him and exalted in showing “his daughter” off to guests, as well as talking to the painting as if it were her when he grew more despondent. “I bid you bonsoir a dozen times before I shut you in that dark case. I can never do it without regret. It seems as if I were burying you alive.” (A. Burr to T. Burr Alston, after August 1808). I couldn’t find confirmation of which of the many portraits Burr had done of his beloved daughter was the traveling companion, so in FoV, I depict it as this one, in part because I think it does the best job of capturing both Theo’s acknowledged beauty and her spritely personality.]

Okay, I promised to do some posts related to The Flight of Virtue and its time period, and I figured I might as well start with my POV protagonist, Theodosia Burr Alston (1783-1813), the daughter of reviled American Founding Father Aaron Burr (1756-1836). Raised by her adoring but exacting father to be a new woman for a new country and a new century, Theo was a child prodigy whose tragic life and mysterious death would ultimately prove her to be a woman too far ahead of her times. But because FoV is less strictly historical in its plot than, say, The God’s Wife, it won’t give away the story to talk about my girl and her extraordinary life. So if you haven’t indulged me yet, don’t worry—consider this more of a context aperitif than a spoiler space.

Theo was born June 21, 1783 as the eldest and only surviving child of Aaron Burr and his wife, Theodosia Bartow Prevost Burr (1746-1794). For those of you who escaped Hamilton-mania eight (!) years ago and can’t recite “Wait For It” from memory, the relationship between Burr and Theodosia the Elder began in a romantic and somewhat salacious manner appropriate to the revolutionary era during which they met. Theodosia Prevost was at the time married to Jacques Marcus Prevost, a Swiss national serving in the British army, though he primarily served in the West Indies during the American Revolutionary War and not in the mainland theater. This was fortunate for Theodosia, as she was a staunch Patriot and her home in New Jersey, The Hermitage, became a well-known gathering place and salon for the American officer corps. George Washington even used The Hermitage as his headquarters after the Battle of Monmouth in July 1778, which is how Burr, a colonel (for this brief moment) attached to Washington’s staff, first met his future wife.

[Portrait of Aaron Burr, John Vanderlyn (1802). This portrait is a companion piece to the painting of Theo above, meant to be hung so father and daughter are facing one another.]

There seems to have been an instant attraction between the twenty-two year old Burr and the thirty-two year old Theodosia, and soon Burr became the talk of the army for sneaking through British pickets in New York City and the New Jersey border to steal moments with his married friend throughout the war. In 1781, Jacques Prevost did them the favor of dying of yellow fever in Jamaica, and within a year, the formerly illicit lovers were married. Marriage also brought instant parenthood to Burr, who became stepfather to Theodosia’s two sons, John Bartow and Frederick. Though admittedly, that had been a role he had been filing for several years now, and the boys seem to have had little trouble switching their affection from their often-absent father to Burr.

Much like John and Abigail Adams, and unusually for the era, Burr and Theodosia Prevost enjoyed an intellectual partnership as strong as their physical compatibility. But unlike Adams, who still laughed at his wife’s famous admonition to “remember the ladies” in the drafting of the new federal constitution, Burr, for all his many other faults, truly held his wife as his equal. Some of this was likely due to Burr’s familial heritage of study and education. Burr was the grandson of the great Calvinist reformer Jonathan Edwards (1703-1758), and although Edwards is famous for his fiery assertions against mankind (he is the progenitor of the idea that men are “sinners in the hands of an angry God”), he was a staunch advocate for the intellectual development of both sexes. Burr’s mother, Esther, and her sisters were raised with the same vigorous education as their brothers, and although both she and Edwards would die during the same smallpox epidemic when Burr was a toddler, their legacy ran deep in his orphaned upbringing among his relations. The surviving (we’ll get to the ‘why’ of that a little later) letters between the Burrs throughout their courtship and marriage are full of discussions of philosophy, literature, and political theory.

[Wikipedia used to have this picture on Esther Edwards Burr’s page as supposedly of her, but if it’s anyone in the Burr family, it’d have to be Theo. Look at that Empire-style dress—her grandmother would have never worn something like that.]
[Actual portrait of Esther Edwards Burr]

But perhaps because of his interactions with his Edwards aunts and his wife, Burr became an unusually early advocate for women’s education. So when destiny delivered a daughter into his hands that June day in 1783, from the moment of her birth, Burr was obsessed with the idea of molding her into what would be for his world a new kind of female creature. When in my flavor text Burr speaks of the idea of women “having souls,” what he means is countering the prevailing wisdom of the time, even in supposedly liberty-loving nations like the United States and revolutionary France, that women were incapable of the highest human achievements. They could paint, but they’d never produce an artist like da Vinci or Raphael; they could read philosophy perhaps, but they’d never be Rousseau or Voltaire—in short, “genius” was beyond their abilities. Burr decided to turn his infant daughter, named for her intellectually curious mother, into the greatest experiment of his life: whether, given the same training and opportunities as a man, his daughter could become the genius her sex was held unable to be.

[Theodosia Burr, Gilbert Stuart (1794). Her father hated this portrait—he disliked the “pensive, sentimental air” the celebrated portrait artist gave Theo, saying it made her look like a “love-sick maid” rather than the heroic idea of her he carried about in his head. (A. Burr to T. Burr, January 5, 1795)]

The younger Theodosia—perpetually “Theo,” “Priss,” or “Prissy” to her parents—was from a very young age given the rigorous course of study reserved for gifted boys in a society where sixteen year olds could graduate from Harvard. And Burr, despite his deep adoration for his daughter, was merciless—surviving letters to Theo from her childhood are riddled with corrections and nitpicks over her progress, or depending on his mood, apparent lack of. A particularly devastating one in January 1794 spends more time arguing with a ten year old Theo about her word choice in a letter she wrote to him on behalf of her rapidly dying mother than addressing both Theodosias’ actual concerns. Despite this, Theo idolized her father and aside from a few understandable small rebellions against her workload, she generally did as she was told.

[Copy of a John Vanderlyn painting of Theo from around the same time as the Stuart portrait (1794/95). Note the much more heroic, Jacobin style.]

Harsh as it was, Burr’s Tiger Mother approach was undeniably successful. By the time she was in her early teens, Theo was fluent in seven languages other than English (French, Latin, Greek, Italian, German, Spanish, and Hebrew), studied the sciences and advanced mathematics in a time where calculus was new, and was extremely well-read in literature and philosophy. On top of becoming sufficiently adept in more feminine accomplishments like music and art at the same time as her more masculine curriculum, Theo was also a trained fencer, a crack markswoman, a strong swimmer, and an expert equestrian. We have more than one letter between her parents where her mother bewails the near-impossibility of keeping Theo on track in all of her studies to Burr’s satisfaction—something no doubt instantly appreciated by any parent with a child in too many activities. Indeed, it is a miracle that the chronically ill Theodosia Prevost, who spent most of her daughter’s crammed childhood slowly dying of what we believe was uterine cancer, managed as well as she did.

[Engraving of Theo (possibly based on a Vanderlyn painting) from 1796/97, when Theo was thirteen or fourteen.]

While Burr and Theo had always been very close, most Burr scholars agree that Theodosia Prevost’s death in the spring of 1794 was a sort of Rubicon for their relationship. Stripped of his wife and intellectual partner, Burr would largely transfer the remainder of his emotional and intellectual world onto the shoulders of his not yet eleven year old daughter. The result of this would lock the two of them in a mutual dependency that in its best light is treated by historians as a relationship that transcended their parent/child bond, and in its worst bordered on emotional incest. Even though other widower American politicians of the era, like Thomas Jefferson, relied on their daughters to fill social functions and handle the familial emotional labor left vacant by deceased spouses, even at the time, Burr and Theo were seen as a particularly intense, morbid, iteration of this.

The excessive, almost unseemly, nature of their codependence tinges every aspect of Burr scholarship—from the overt historical ick-factor of Burr addressing his private journals during his political exile in Europe to Theo and detailing all of his sexual encounters to her; to the fact that when novelist Gore Vidal made up the plot point that the “despicable” accusation Alexander Hamilton got shot over rather than repeat to Burr’s face was that Burr had committed physical incest with Theo, the idea was so believable that serious academics have to address it in pretty much any book about either father or daughter. Personally, I agree with the majority that it is almost certainly not factually true, but I also agree with Vidal that such an accusation is exactly the sort of monumentally stupid thing incorrigible blabbermouth Hamilton would have let fly on the spur of the moment and then been completely unable as a gentleman to admit to having said. But in the end, it’s all conjecture.

[A so-called “lover’s eye” painted by John Vanderlyn. Lover’s eyes were briefly fashionable during the Regency Era, generally commissioned to depict a single eye (sometimes another body part like a mouth or an ear) and given to an intimate partner. While technically the young woman’s eye in this portrait is unknown, its shape and color, combined with the mischievous spark lurking in it, bear a striking resemblance to Vanderlyn’s portraits of Theo. There has always been speculation that there might have been an attraction between Vanderlyn and his earliest muse, supported by the fact that Burr packed the painter out of his house and off to Paris just as Theo hit her teens, and that Vanderlyn never married. But if this lover’s eye, kept in the painter’s own collection, is Theo, it might just as well be a saucy joke between old friends as evidence of an unrequited love.]

The acuteness of Burr and Theo’s emotional collusion also inevitably colors any discussion of Theo’s marriage to Joseph Alston (1779-1816). Because Alston was from a wealthy South Carolina planter family, and wasn’t considered particularly attractive or intellectual himself, many in Northern political circles at the time believed that the ambitious Burr, newly elected as Vice President, had essentially sold his gifted daughter to gain southern allies for a future presidential bid. And, Theo, being her father’s adoring puppet, merely went along with it to please him. Certainly Theo was on the younger side of marriageable age at eighteen (contrary to what you might think, colonial-era marriages tended to skew well into the twenties for both sexes), and lord knows the Alstons’ money probably helped the perpetually insolvent Burr with his creditors, but I think this dim view of the Alston marriage comes with a lot of historical baggage. For all his tough love, Burr worshipped his daughter and having her living so far away couldn’t have been his first choice. And to view the marriage as solely one of convenience ignores the many fond letters we have both between Theo and Alston, and from Theo to her father where she speaks lovingly of her husband even behind his back. Both father and daughter generally refer to him in their correspondence as Mari—“Husband” in French—a definite sign of affection from the Francophile Burrs.

The ulterior motive angle largely comes from Burr’s political rivals both before and after his fall from grace, and they saw treachery in everything he did, which makes them unreliable witnesses. There is also a touch of romantic revisionism among the New York literati Theo grew up around because she and American writer Washington Irving (1783-1859) were childhood friends, and a lot of people liked the idea of the latterly-famous Irving and the sophisticated Theo married and running a world-famous literary salon together rather than Theo “throwing herself away” on the unremarkable Alston.

[Joseph Alston]

In the real world, I think it’s just as likely Theo fell in love and the heart wants what the heart wants. In FoV, I do play up the money-for-Dad angle a little, but as to why a young woman like Theo might find Alston attractive, I also put forward the idea that she already had one lovably impossible man in her life and maybe she was drawn to someone who was so much less complicated and demanding than her father. Joseph Alston, despite serving as governor of South Carolina during the War of 1812, is mostly a historical cipher, but one thing that shines through in the record is his obvious adoration of his beautiful, talented wife despite her often controversial father. He seems to have devoted most of their twelve-year marriage to making her (and by extension, Burr) happy and her death appears to have completely shattered him, as he died himself barely three years later at the age of only thirty-six. What I’m saying is the man deserves more than to be treated like he was unworthy of Theo. Because even Theo understood that it wasn’t always easy being married to her, and by extension, her father. Obviously having his father in law, the sitting US Vice President, shoot a political rival dead in an illegal duel, and then later possibly trying to extrajudicially annex Mexico didn’t exact make Joseph Alston’s life a walk in the park. But even more than Papa Burr’s antics, Alston was worried about his increasingly sick wife.

Like with her mother’s illness, we don’t know precisely what was wrong with Theo, in part because medicine of the period was generally bad and women’s medicine especially so. But most historians agree that it was likely a gynecological disorder; either she had uterine or cervical cancer like her mother, or possibly was suffering from a prolapsed uterus. The latter is suspected because Theo never enjoyed consistent good health after the birth of her only child, Aaron (obviously) Alston, in 1802—which may point to some medical trauma from the delivery. Either way, her health went into steady decline and took with it much of the promise of her youth. Burr, who blamed the marshy southern climate for her illness, still pushed her to write and read as she’d once done, but it’s clear that everything became increasingly difficult for Theo to manage. She would occasionally rally for the sake of her father—like when she traveled to Richmond for his treason trial and dazzled his friends and enemies alike to help him avoid the noose—and she struggled to be there for her cherished son, but usually if she was well enough to leave her bed, she was seeking out restorative spas in Upstate New York for cures.

After the fallout of his political demise, Burr spent most of 1807-1812 in exile in Europe, during which Theo tried to handle his affairs stateside and use what remained of her fading strength to cajole any of their remaining allies to smooth his way home. She finally succeeded in the spring of 1812, but a month before her father’s return, her son died of malaria and the loss sent Theo’s precarious health into a tailspin. Burr reached New York in July, but Theo was so incapacitated that it would take until the end of December for her to be well enough to travel even for the sake of her father. Finally, she booked a passage on a privateer schooner, The Patriot, and sailed for New York to be reunited with her father—her closest confidante, her creator, her best friend—for the first time in five years. The Patriot, and Theodosia Burr Alston, were never seen again.

[Theodosia Burr Alston, John Vanderlyn (1815-20). The fact that this portrait of Theo is thought to have been painted after her disappearance shows how she continued to be a muse to Vanderlyn throughout his life.]

Theo’s disappearance at sea caused a sensation in its own time and there is a wealth of contemporary folklore that sprung up in its wake, much to the dismay of her devastated father and husband. The simplest and most likely scenario is that The Patriot sank in a storm somewhere off the coast of Nags Head or Cape Hatteras in North Carolina, a very common occurrence during the period, and all hands drowned. Logs from British naval ships blockading the American coast report a particularly bad storm that raged from the afternoon of January 2nd through the 3rd, which was the last time anyone heard anything from The Patriot. Similarly, in those areas, local “wreckers” or “bankers” would sometimes lure ships onto the shoals in order to loot their cargos after the crew and passengers had drowned, so The Patriot could have sank in a man-made wreck as well. The so-called “Nags Head Portrait,” said to have been found by wreckers during the war is sometimes thought to be of Theo, though experts are divided and the only member of the Alston family to have seen both the real Theo and the painting (her sister in law, Mary) didn’t think it was a likeness of her. Based on the many paintings of her by John Vanderlyn, I’m inclined to think it isn’t her (the jawline and shape of her head seems wrong), but it’s anyone’s guess.

[The Nags Head Portrait]
[Honestly, I think this Vanderlyn painting of Ariadne looks more like Theo (in the face) than the Nags Head Portrait—make of that what you will]

But the most popular and persistent stories were the various pirate-related ones, for understandable reasons. Wikipedia lists at least four different variations on the theme, and my research turned up at least one other, but in short, people loved the pirate angle. Be it the noble Theodosia hacked to death by a pirate raiding party; left naked and chained to the bulkhead of The Patriot on the Gulf coast; carried off by a smitten buccaneer; or—the clear favorite of the 19th century public—tragically forced to walk the plank at sword point (to best display her beauty and nobility), Theo’s pirate-related demise is the legend that cannot die.

It is also the version of her end that is practically impossible to ignore as a novelist, but I wanted to play with these ideas outside of the strictures of the (clearly male-driven) fictional fantasies of the men of her time. Because, you tell me: even if she was grieving and at death’s door, do you really think that the young woman (she wasn’t even thirty yet) who was raised by the Aaron Burr to be the smartest and most capable woman of her generation would go down without a fight to mere pirates? As I explained to my editor, anyone who comes up with a fictional pirate story about this fierce, unusual woman that isn’t “Theodosia: Pirate Queen” clearly doesn’t know who they’re dealing with. Reign on, Theo—if only in our imaginations 🏴‍☠️

[“Theodosia walking the plank” (Illustration from The Century Magazine; reproduction from Theodosia Burr Alston (Richard N. Côté, 2005))]
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