The so-called “Nag’s Head Portrait”, possibly of Theodosia Burr Alston. (Photo: Public Domain)

In 1869, a vacationing doctor named William Gaskins Pool was called to help an ill old woman named Polly Mann, who lived in a shack near Nags Head, Carolina. When he and his daughter, Anna, gingerly entered the dark, cobweb-covered home, they were drawn to a picture on the wall, Anna remembered, “of a beautiful young woman about twenty-five years of age.” After extensively questioning Polly about the painting, Dr. Pool believed his initial hunch was correct. He was staring at a portrait of the long vanished Theodosia Burr Alston, a portrait which may hold the key to her long-debated fate at sea.

Today, if people know anything about Theodosia, it is because of the lovely lullaby “Dear Theodosia,” sung by the character of Aaron Burr in the sensational musical Hamilton. But the real-life Theodosia grew from a beloved child into a highly intelligent, complex adult, whose fascinating story is largely unknown and worthy of its very own Broadway smash.

Theodosia Bartow Burr was born in Albany, New York, on June 21, 1783. Her mother, also called Theodosia, was a brilliant, cultured woman. She had scandalized New England society, when as a married mother of five, she fell in love with an equally brilliant and much younger blue-blooded lawyer and Revolutionary War soldier—Aaron Burr. After her first husband’s death, the two were married, and little Theodosia, the couple’s only child to survive, became the center of her parents’—particularly her father’s—world.

“Your dear little Theodosia cannot hear you spoken of without an apparent melancholy,” the elder Theodosia wrote to a traveling Aaron in 1785, “insomuch that her nurse is obliged to exert her invention to divert her, and myself avoid to mention you in her presence. She was one whole day indifferent to everything but your name. Her attachment is not of a common nature.”

Aaron Burr, Theodosia’s father. (Photo: Library of Congress/LC-USZ62-102555)

Aaron reciprocated these feelings. His plans for his lovely, dark-haired “Little Miss Priss,” who was already displaying an extraordinary intellect and sharp wit, were incredibly ambitious, and for the times, highly progressive. “I hope yet by her [Theodosia] to convince the world what neither sex seems to believe,” he wrote, “that women have soul!”

In 1800, Theodosia became deeply enamored with Joseph Alston, a wealthy planter from South Carolina. “My father laughs at my impatience to hear from you,” Theodosia wrote teasingly to Joseph during a separation.

The couple were married on February 2, 1801, in Albany. Little more than a month afterwards, she and her new husband watched as her father was sworn in as Vice-President of the United States, under President Thomas Jefferson. They were further blessed nine months later when their son Aaron Burr Alston, nicknamed “Gampy” by his doting grandfather, was born.

However, the birth of her only child took a heavy toll on Theodosia. She was severely injured during the traumatic birth, and the prolapsed uterus she suffered left her in immense pain, and made intercourse impossible. Although she adored her husband and his family, she had a hard time adjusting to the isolated life of a plantation mistress at The Oaks, the family estate on the Waccamaw River in South Carolina, and was soon spending half the year in New York with her father.

Theodosia Burr Alston, pictured in 1802. (Photo: New York Public Library/Public Domain)

On July 10, 1804, Aaron sat down at his desk and wrote his Theodosia a letter of goodbye. “I am indebted to you, my dearest Theodosia, for a very great portion of the happiness which I have enjoyed in this life. You have completely satisfied all that my heart and affections had hoped for or even wished.” The next day, Aaron—still the Vice President of the United States—would kill Alexander Hamilton in a duel in Weehawken, New Jersey.

Rumors swirled as to the cause of the duel. Aaron had been incensed by a comment Hamilton had made about “still more despicable” acts. Some thought Hamilton may have been referring to Aaron and Theodosia’s “morbid affection” for each other, which had led to whispers of incest.

Whatever the case, Aaron was soon on the run, although he was never tried for the murder. After serving out his term as Vice President, Aaron headed west to establish a new country comprised of western North American territory and Mexico. He planned to become emperor of said country, with Theodosia succeeding him as empress. He had the full support of his daughter and son-in-law, who supplied much-needed funds. The Alstons even headed west to help Aaron in his quest. Theodosia wrote to her half-brother excitedly about “the new settlement which I am about to establish.”

But the Burr dynasty was not to be. The plot was found out, and Burr was taken into custody. In 1807, he was tried for treason in Richmond, the ever loyal Theodosia at his side. Amazingly, Aaron was acquitted, and with the help of Theodosia he soon smuggled himself out of the country and headed for Europe.

Her father now gone, Theodosia’s health—she was probably in the final stages of uterine cancer— deteriorated further. “The most violent affections have tormented her during the whole of the last 18 months,” she wrote in third-person to a doctor in 1808. “Hysteric fits, various colors and flashes of light before her yes, figures passing around her bed, strange noises, low spirits and worse.” She missed her father intensely. “What indeed,” she wrote him, “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.”

In 1812, Theodosia’s beloved “Gampy” died of malaria in South Carolina. With the loss of her only child, Theodosia’s world grew darker. “There is no more joy for me,” she wrote. “The world is blank. I have lost my boy.”

Theodosia Burr Alston. (Photo: Public Domain)

On December 10, 1812, Joseph Alston was elected governor of South Carolina. His new position made it impossible for him to accompany Theodosia to New York, and with the War of 1812 raging in the Atlantic, he was worried about his frail wife making the treacherous trip to New York. To ensure his daughter’s safety, Aaron sent down his friend Dr. Timothy Green to secure a boat and make sure that Theodosia made it home to him.

Theodosia, along with Dr. Green, a French maid and skeleton crew, boarded a small schooner called the Patriot at the port of Georgetown on December 31. One week passed, then two, then three—with no word from the Patriot, its small crew or passengers. “In three weeks I have not yet had one line from her,” Joseph wrote Aaron. “My mind is tortured—after 30 days—my wife is either captured or lost!” By February 24, he had given up all hope. “My boy and-my wife- gone both! This, then is the end of all the hopes we had formed,” he wrote to his father-in-law. “You may well observe that you feel severed from the human race. She was the last thing that bound us to the species.”

Within weeks of the Patriot’s disappearance, rumors about Theodosia’s fate began to spread in the North and the South. Joseph died in 1816, a shell of the man he once was. Burr lived another 23 years, long enough to witness the cottage-industry of conspiracy theories about his daughter’s disappearance come to life. He refused to believe she was still alive, stating firmly: “She is dead. She perished in the miserable little pilot boat in which she left. Were she alive, all the prisons in the world could not keep her from her father.”

Many believed the Patriot had been captured by one of the pirate ships known to troll the Outer Banks. Over the years, numerous “death-bed confessions” from various aged or imprisoned pirates were reported in papers all over the country. The first to gain traction was the case of Jean DeFarges and Robert Johnson, who were executed in 1819 for other crimes. An 1820 article in the New York Advertiser claimed that the two had confessed to having been crew on the Patriot. They claimed to have led a mutiny, and scuttled the ship, killing all on board.

In 1833, The Mobile Commercial Register reported that another man had confessed to raiding the Patriot with other pirates, who had reluctantly forced Theodosia to walk the plank. Other stories claimed that she had become the wife of an American Indian in Texas, been taken as a pirate’s mistress to Bermuda, or that she had killed herself after resisting the advances of the pirate Octave Chauvet. Yet another fanciful story had her writing farewell letters to her father and husband, and stuffing them and her wedding ring into a champagne bottle and throwing it into the Carolina sea before being executed.

Perhaps the most oft-repeated “confession” was that of Benjamin F. Burdick, a “hard, rough old salt” of a sailor. On his death bed at a poor-house in Michigan, he is said to have confessed to a minister’s wife that he had been on the pirate ship that overtook the Patriot. According to an 1878 edition of the New York Times:

He said there was one lady on board who was beautiful appearing, intelligent and cultivated, who gave her name as Mrs. Theodosia Alston. When her turn came to walk the fatal plank she asked for a few moments time, which was gruffly granted her. She then retired to her berth and changed her apparel, appearing on deck in a few moments clad in pure white garments. And with a bible in her hand, she announced that she was ready. She appeared as calm and composed as if she were at home, and not a tremor crept over her frame, or a pallor overspread her features, as she walked toward her fate. As she was taking the fatal steps, she folded her hand over her bosom and raised her eyes to heaven. She fell and sank without a murmur or a sigh.

Then there is the curious case of “the female stranger,” who is buried in the St. Paul’s Episcopal Graveyard in Alexandria, Virginia. It is said this “veiled lady” appeared in the city in 1816, with a man claiming to be her husband. She died a short time later. Legend has it that this was Theodosia and Dr. Green, recently returned from captivity in the islands.

Perhaps the only clue we have as to what really happened to Theodosia is the Nags Head portrait, discovered by Dr. Pool in 1869. According to his daughter, Polly Mann told her and her father that her deceased husband, Joseph Tillett, was a “wrecker” who scavenged the ships that washed up on the shores of the Outer Banks. She claimed that decades before, he and his friends had come upon a scuttled, empty schooner near Kitty Hawk. In one cabin they found many fine items, including the portrait and dresses, which were now in Polly’s possession. “Also exposed to our view—a vase of wax flowers under a glass globe,” Anna remembered, “and a shell beautifully carved in the shape of a nautilus.”

A drawing of Burr Alston from 1900, based on a 1811 miniature. (Photo: Public Domain)

Polly gave the portrait to Dr. Pool in lieu of payment. He took it back home to Elizabeth City. Over the years, he and his cohorts would attempt to get authentication of the portrait from the Burr and Alston families, whose opinions as to whether the likeness was Theodosia varied greatly. “I do remember her beautiful eyes,” Joseph Alston’s youngest sister wrote, “and the eyes in the picture are really beautiful.”

Those who believe in the painting’s authenticity think it proves that Theodosia died off the coast of the North Carolina shore, one way or another. There were fierce storms on the Outer Banks January 2nd and 3rd in 1812, which caused damage to ships nearby the Patriot’s planned route. It is most likely that the small ship was simply over-powered by the storm, but who knows? Perhaps pirates, rogue wreckers, the British, or something else caused the boat’s destruction. Or perhaps Theodosia was spirited away to some exotic land, and lived a long life—though in her precarious health that seems very unlikely.

Today the legend of Theodosia lives on. The Nags Head Portrait now hangs in the Lewis Walpole Library at Yale. Her ghost is said to haunt her plantation The Oaks, the Outer Banks, Richmond Hill and Bald Head Island, where it is said her spirit is chased by three headless pirates. In the late 19th and early 20th century the mystery was spun into several novels and countless magazine articles. Many little girls were named after her—including Theodosia Burr Goodman, who would become famous as the silent screen vamp Theda Bara. Her story was a favorite of poets, including Robert Frost, whose poem Kitty Hawk includes the line:

Did I recollect how the wreckers wrecked Theodosia Burr off this very shore? T’was to punish her, but her father more.

But perhaps the impact of the mystery of Theodosia is best summed up by her friend Margaret Blennerhasset in her poem On A Friend Who Was Supposed To Have Suffered A Shipwreck: