The Heartbreaking Disappearance of Theodosia Burr Alston

She was the famous daughter of American villain, Aaron Burr, and became one of our country’s oldest and most perplexing unsolved mysteries

From her first breath, Theodosia Bartow Burr was her father, Aaron Burr Jr’s pride and joy. She was born on June 21, 1783, in Albany, New York, and named after her mother, Theodosia Stillwell Bartow Prevost Burr. Aaron Burr not so secretly courted the elder Theodosia, a mother of five, and the wife of British officer Jacques Marcus Prevost. Jacques died in 1781. Aaron married his one true love on July 2, 1782, at her family’s estate in New Jersey, The Hermitage.

The marriage was amicable but short and marred with tragedy. Theodosia, the mother, delivered three stillborn sons and suffered many miscarriages. Mr. and Mrs. Burr had one other daughter, Sarah who was called Sally, who died of an illness in 1788. Regarding the death of their youngest daughter, Mrs. Burr wrote:

“Variegated have been my scenes of anguish, but this exceeds them all…She passed gently from me to the region of bliss…My Sally, she is gone.”

Six short years later, Mrs. Burr passed away, likely of uterine cancer. Aaron Burr was heartbroken. In his despair, he resolved to provide a stable and loving childhood for his beloved remaining daughter. As a feminist, he desired to educate Theodosia as well as any son.

Her Father’s Daughter

Theodosia was a charming child who inherited her father’s brilliant mind and her mother’s beauty. She possessed an aptitude for language, art, and arithmetic. Aaron Burr had a busy law practice throughout Theodosia’s childhood, and then came politics.

Theodosia came of age in a new country, where her father was Vice President. There was no shortage of suitors eager to court Aaron Burr’s beautiful prodigy of a daughter. Only one such suitor caught Theodosia’s attention.

Joseph Alston was a handsome southern aristocrat from a wealthy South Carolina family. The couple exchanged letters frequently and often discussed the ups and downs of marriage at a young age. Before long, they became engaged. 18-year-old Theodosia married Joseph Alston at her home in Albany on February 2, 1801. The couple made their home at the Alston family plantation, The Oaks, in Georgetown County, South Carolina.

Homesick

Theodosia loved her husband but detested the south. The weather was sticky and uncomfortable, and the social climate was stifling. The Alston family owned, at times, upwards of 200 human beings. Like her father, Theodosia abhorred slavery. At one time, Aaron Burr sought to abolish the institution.

Even so, the Burr’s owned slaves. He was particularly fond of his valet, an enslaved person named Carlos. Sure, the Burr family treated their slaves better than most, which isn’t saying much, but he saw to their education. He even joined the New York Manumission Society and, in 1784, proposed a bill to abolish slavery nationwide. It didn’t pass, and Burr still failed to free his slaves.

Within one year of marriage, Theodosia became pregnant. Conflicted as she was, Theodosia resolved to make the best of her new life. On May 29, 1802, Theodosia welcomed a healthy son, Aaron Burr Alston. The labor was arduous and left Theodosia with a painful prolapsed uterus. However, the baby was a welcomed addition to the family, and Aaron Burr had grand plans for his grandson’s upbringing.

In Her Father’s Shadow

Aaron Burr was ahead of his time in regards to slavery and feminism. He was also overly ambitious, arrogant, and his hot temper frequently clouded his judgment. Such was the case on July 12, 1804, when his 15-year rivalry with Treasury Secretary Alexander Hamilton famously cumulated in a duel that killed Hamilton.

Aaron Burr, charged with murder, fled to the south, no doubt near Theodosia. Though the murder charge didn’t stick, his reputation never recovered. He finished his term as vice president, but new trouble lingered around the corner. In 1807, he led a party to create a new country from the western states and invade Mexico. The plan failed phenomenally when soldiers in Louisiana captured the former Vice President.

A jury found Aaron Burr not guilty, though he was ostracized in his social and political circles. Theodosia, who was ever faithful to her father, became something of an outcast.

Her father fled to Europe to distance his legal problems, many enemies, and recover his reputation. He remained there for four years. During his time in exile, Burr had no communication with his daughter. He kept a journal where he penned one-way conversations with her. Someday, he hoped to show her how she never left his thoughts.

“What indeed would I not risk once more to see him, to hang upon him, to place my child upon his knee, and again spend my days in the happy occupation of endeavoring to anticipate his wishes.” — Theodosia Alston, regarding her father.

The Unimaginable

“Theodosia has endured all that a human being could endure, but her admirable mind will triumph. She supports herself in a manner worthy of your daughter.” — Joseph Alston to Aaron Burr, July 26, 1812

Theodosia had little left for her in the States. With her father unwelcome on this side of the Atlantic, she immersed herself in her role as wife and mother. Her father returned to New York in June of 1812. Sadly, on June 30, 1812, Theodosia’s son succumbed to malaria at just ten years old. She was inconsolable. “There is no more joy for me,” She wrote, “I have lost my boy. He is gone forever.”

During the bleak days following her son’s death, Theodosia learned that her father was once again in New York. To Theodosia, her father’s homecoming was a light in her very dark world.

Theodosia planned an end of the year trip to her home town where she would reunite with her father. Her husband was understandably trepidatious about the voyage.

The War of 1812 was in full swing when Theodosia planned to sail up the east coast. Joseph couldn’t accompany his wife; he was recently elected governor of South Carolina and in charge of the state militia and, therefore, duty-bound to remain. He feared for Theodosia’s safety due to her position as his wife, especially during war. There were also rampant rumors of pirate activity on the Carolina coasts. He was also concerned about her health. Sadly, Theodosia never recovered from her son’s difficult birth and experienced chronic, debilitating pain. But she was determined and persuaded her husband to consent to the trip.

As a precaution, Aaron Burr hired a privateer, a schooner called the Patriot, to bring Theodosia north. He also retained a small entourage of caretakers, including a maid and a family friend, doctor Timothy Green, who would accompany the grieving socialite.

On December 31, 1812, Theodosia packed elegant silk dresses and a portrait of herself. The painting was a gift to her father. She kissed her husband goodbye and boarded the Patriot at Georgetown. The journey would take approximately a week, depending on the conditions at sea.

A week came and went, but the Patriot never arrived in New York. The schooner and passengers, including Theodosia Burr Alston, were never seen again.

Lost at Sea

“Did I recollect
How the wreckers wrecked
Theodosia Burr
Off this very shore?
’Twas to punish her,
But her father more…” —
Excerpt from the 1953 poem, Kitty Hawk, Robert Frost,

Aaron Burr could not escape terrible rumors regarding his daughter’s fate. Indeed, there is no shortage of deathbed confessions of pirates willing to take credit for her tragic death.

Two pirates were apprehended and brought to Norfolk, Virginia, in 1832. After a trial resulted in a death sentence, the men made an unexpected confession. They insisted they used lights secured to a hobbled horse and lured the Patriot and forced everyone to walk the plank near Nags Head, North Carolina.

A Texas sailor confessed he, along with the Patriot’s crew, revolted and killed the officers aboard. He also claimed they forced the passengers to walk the plank. The sailor specifically recalled Theodosia. According to his version of events, she was the last to die. The look of pure terror on Theodosia’s face haunted him for the remainder of his life.

In 1833, Michigan resident, Frank Burdick, made a deathbed confession. Like the others, he claimed to be a pirate. His role in the crime included holding the plank while a blindfolded Theodosia tiptoed into her death. In her last moments, she asked that he tell her father what became of her.

In 1833, an Alabama newspaper printed the story of a local man who was a former pirate, admitted plundering the Patriot, and murdering everyone on board. Like the others, he claimed this occurred near Nags Head. All of these self-proclaimed pirates had the same story, but none offered proof.

In 1870, a cousin of Theodosia’s named Stella Edwards Pierpont-Drake visited North Carolina to pursue a single piece of evidence rumored to exist — a portrait. The portrait’s subject was said to be Theodosia Burr Alston, but the family disagreed about the sitter’s identity. At the time, It was owned by Dr. William G. Pool of Elizabeth Town, North Carolina. The story of how he came to possess it was extraordinary.

Twenty years earlier, Dr. Pool paid a house call to Polly Mann, of Nags Head. The Mann’s small, ramshackle home suggested they were not wealthy people. Yet, hanging in their living room was a beautiful, expensive, antique painting of a woman who bore a striking resemblance to Theodosia Burr. The subject was clad in a delicate white gown with lace trim. She had piercing dark eyes and a Mona Lisa grin.

Dr. Pool asked to buy the portrait, but Mrs. Mann wouldn’t hear of it. To her, it had sentimental value that she couldn’t put a price on. Before Polly was married, she had a romance with a young fisherman named Joseph Tillett.

Aside from fishing, Tillett made money as a “wrecker,” a person who salvaged abandoned ships that washed ashore. During her courtship, Mrs. Mann claimed that Joseph, along with other wreckers, discovered a deserted schooner near Nags Head. The schooner was mostly empty and destroyed. However, one cabin appeared to have been occupied by a woman; inside were several silk gowns and the elegant painting. In place of pay, Joseph scavenged these items and gave them to his sweetheart, the future Mrs. Mann.

Mrs. Mann gifted the portrait to Dr. Poole to show appreciation for his exceptional care after her recovery. No one has officially identified the sitter. However, Mrs. Pierpont-Drake published a photograph of her sister next to the Nags Head portrait. The resemblance is uncanny, if coincidental. She believed beyond a doubt that the picture was of Theodosia Burr Alston. The Nags Head Portrait now hangs at hangs in the Lewis Walpole Library at Yale.

The Stranger

For Aaron Burr, the worst of the rumors were those insisting Theodosia lived. He knew his daughter well, and if she disembarked the ship alive, he believed she would have contacted him. Sightings of Theodosia were endless, as were women claiming to be her. The most famous being a stranger who drifted into Alexandria, Virginia, in 1816.

The “Female Stranger” wore a veil and kept company with an older man who claimed to be her husband. The woman was very sick. Her husband asked a doctor to care for her, but not to question their identities. Unfortunately, the woman passed away on October 14, 1816. When she did, the husband fled town, leaving behind several gambling debts and an unpaid bar tab. Some say the woman was Theodosia. This myth persists today.

In truth, the Patriot likely foundered at sea due to a documented storm with gale-force winds. Between January 2 and 3, 1812, violent storms plagued the Patriot’s route up North Carolina coast. Other ships reported damage and loss, suggesting that the Patriot sank with passengers and crew. Theodosia’s husband was heartsick when there was still no sign of Theodosia, dead or alive by the end of February. On February 24, 1813, Joseph Alston wrote to his father in law:

“My boy and my wife, gone both! This, then, is the end of all the hopes we had formed. You may well observe that you feel severed from the human race. She was the last thing that bound us to the species.”

Aftermath

Nearly two centuries have passed, and we are as close to solving the mystery of the Patriot’s disappearance now as we were then. Theodosia’s tale has been the subject of works of poetry and fiction ever since. The beginning of her life has recently been memorialized with a sweet lullaby, Dear Theodosia, in Lin-Manuel Miranda’s musical, Hamilton.

Further Reading

Theodosia Burr Alston: Portrait of a Prodigy; Richard Cote

Duel of the Heart; Rose Moore Tomlin

Memoirs of Aaron Burr; Aaron Burr with Matthew Livingston Davis

Theodosia, the First Gentlewoman of Her Time: The Story of Her Life, and a History of Persons and Events Connected Therewith; Charles Felton Pidgin

Welcome readers! Heather Monroe is a genealogist and writer who resides in California with her partner and their nine children. •True Crime• History• Memoir•

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store