Acquitted but still politically ambitious, Burr purportedly schemed to convince several western states to secede and make him the head of the government. In 1807, he defended himself against a conspiracy charge and again Theodosia fully supported him. After a year long, difficult trial, Aaron Burr once again won acquittal and left the United States for exile in Europe.
When Theodosia returned to South Carolina, her health had become more fragile and when her son died of malaria in June 1812, she collapsed. She wrote her father, "Less than a fortnight ago your letter would have gladdened my soul. Now there is no joy, and life is a blank. My boy is gone-forever dead and gone!"
Newly returned from Europe and deeply worried about his daughter, Aaron Burr convinced Theodosia to come to New York for the holidays. Joseph Alston couldn't leave South Carolina and felt uneasy about Theodosia's voyage. The United States and Great Britain were at war, Theodosia's health continued to deteriorate and rumors about pirates along the North Carolina Outer Banks circulated around the Carolinas.
Granting his wife's request, Joseph Alston wrote a letter to the British Navy blockading the coast, asking for safe passage for his wife. Aaron Burr sent a trusted friend and doctor, Timothy Green, to make the voyage with Theodosia and on December 30, 1812 Theodosia, Dr. Green and a maid climbed aboard the schooner Patriot which lay moored in Charleston Harbor. It sailed out of Charleston Harbor, bound for New York City under the command of Captain Overstocks, with an old New York pilot as sailing master.
The schooner Patriot had just returned from several months of West Indies privateering raids for the United States government with a hold filled with booty from these raids. In order to disguise the ship’s true identity, the captain stowed the guns below and painted over the ship’s name on the bow. The sailors lifted Patriot's anchor in late afternoon and the captain set a course for the open sea. Theodosia Burr settled in her cabin with several chests filled with her wardrobe and accessories. Some stories say that she also carried a recent portrait of herself that she intended to give her father as a Christmas gift.
The journey to New York normally took five or six days. After two weeks had passed with no sign of the Patriot, Burr and Alston became frantic. Alston wrote, "Another mail and still no letter! I hear too rumors of a gale off Cape Hatteras at the beginning of the month. The state of my mind is dreadful!" In New York, Burr had already reached the inevitable conclusion. When a friend offered hope that Theo was still alive, Burr replied, "No, no, she is indeed dead. Were she still alive, all the prisons in the world could not keep her from her father."
Theodosia Burr Alston, her fellow passengers and crew, and the Patriot itself were never seen again. The Patriot had disappeared without a trace. Later it was learned that the British fleet had stopped her off Hatteras on January 2. Governor Alston's letter worked, and the schooner was allowed to pass. Later that night, a gale arose and scattered the British fleet. Beyond that clue, no more was known. Burr sent searchers to Nassau and Bermuda with no success. Why he neglected to send them to the Outer Banks remains a mystery for it is there that Theo met her fate.
Following the Patriot's disappearance, rumors immediately arose. The most enduring was that the Patriot had been captured by the pirate Dominique You aka "The Bloody Babe"; or something had occurred near Cape Hatteras, notorious for its wreckers. Her father refused to credit any of the rumors of her possible capture, believing that she had died in a shipwreck. But the rumors persisted long after his death and, after around 1850, more substantial "explanations" of the mystery surfaced, usually alleging to be from the deathbed confessions of sailors and executed criminals.
One story considered to be somewhat plausible was that the Patriot had fallen prey to the wreckers known as the Carolina "bankers". The bankers populated the sandbank islands near Nags Head, NC, pirating wrecks and murdering both passengers and crews. When the sea did not serve up wrecks for their plunder, they lured ships onto the shoals. On stormy nights the bankers would hobble a horse, tie a lantern around the animal's neck, and walk it up and down the beach. Sailors at sea could not distinguish the bobbing light they saw from that of a ship which was anchored securely. Often they steered toward shore to find shelter. Instead they became wrecked on the banks, after which their crews and passengers were murdered.
In 1833 an Alabama newspaper, the Mobile Register, reported that a man "residing in one of the interior counties of this state" made a deathbed confession that he had participated in the capture of the Patriot, the murder of all those on board and the scuttling of the vessel "for the sake of her plate and effects."
In relation to this, a Mr. J.A. Elliott of Norfolk, VA made a statement in 1910 that in the early part of 1813, the dead body of a young woman "with every indication of refinement" had been washed ashore at Cape Charles, and had been buried on her finder's farm.
Writing in the Charleston News and Courier, Foster Haley claimed that documents he had discovered in the State archives in Mobile, AL, said that the Patriot had been captured by a pirate vessel captained by John Howard Payne and that every person on board had been murdered by the pirates including "a woman who was obviously a noblewoman or a lady of high birth". However, Haley never identified or cited the documents he had supposedly found.
The most romantic legend concerning Theodosia's fate involves piracy and a Karankawa Indian chief on the Texas Gulf Coast. The earliest American settlers to the Gulf Coast testified of a Karankawa warrior wearing a gold locket inscribed "Theodosia." He had claimed that after a terrible storm, he found a ship wrecked at the mouth of the San Bernard River. Hearing a faint cry, he boarded the hulk and found a white woman, naked except for the gold locket, chained to a bulkhead by her ankle. The woman fainted on seeing the Karankawa warrior, and he managed to pull her free and carry her to shore. When she revived she told him that she was the daughter of a great chief of the white men, who was misunderstood by his people and had to leave his country. Before dying in his arms, she gave him the locket and told him that if he ever met white men he was to show them the locket and tell them the story.
Another myth about her fate traces its origin to Charles Etienne Arthur Gayarre's book Fernando de Lemos: Truth and Fiction: a Novel (1872). Gayarre devoted one chapter to a confession by the pirate Dominique You. In Gayarre's story You admitted having captured the Patriot after he discovered it dismasted off Cape Hatteras following a storm. You and his men murdered the crew, while Theodosia was made to walk the plank: "She stepped on it and descended into the sea with graceful composure, as if she had been alighting from a carriage," Gayarre wrote in You's voice. "She sank, and rising again, she, with an indescribable smile of angelic sweetness, waved her hand to me as if she meant to say: 'Farewell, and thanks again'; and then sank forever."
Fifteen years later, another former pirate, "Old Frank" Burdick, confessed a similar story on his deathbed. He told a horrifying story of holding the plank for Mrs. Alston, who walked calmly over the side, dressed completely in white. He said she begged for word of her fate to be sent to her father and husband. He went on to say that once the crew and passengers had been murdered, they plundered the ship and abandoned her under full sail. He also mentioned seeing a portrait of Theodosia in the main cabin.
Because Gayarre billed his novel as a mixture of "truth and fiction" there was popular speculation about whether his account of You's confession might be real, and the story entered American folklore. The American folklorist Edward Rowe Snow later put together an account in Strange Tales from Nova Scotia to Cape Hatteras incorporating the Gayarre story with later offshoots. For example, on February 14, 1903, one Mrs. Harriet Sprague issued a sworn statement before Notary Freeman Atwell, of Cass County, MI claiming to corroborate the details of You's confession in Gayarre's 1872 novel. Mrs. Sprague described the contents of an 1848 confession by pirate Frank Burdick, an alleged shipmate of You's when the Patriot was discovered. The pirates left most of Alston's clothing untouched, as well as a portrait of Alston.
Perhaps the most intriguing evidence to support this theory revolves around that painting. In 1869, a Dr.William G. Poole of Elizabeth City, spending his summer vacation at Nags Head, was called to the bedside of an ailing old Banker woman. The woman, Mrs. Polly Mann, was related by marriage to families who had once made their living by plundering vessels wrecked along the beaches.
The doctor noticed a stunning portrait of a young woman dressed in white hanging on the wall of the woman's shack. When he commented on the beauty of the subject, the old woman offered an astonishing explanation. She told Dr. Poole that one night "during the English war" a pilot boat had drifted ashore at Nags Head at the height of a winter's gale. The boat was abandoned with all sails set, and the name on the bow had been painted over. In the main cabin, the Bankers had found several trunks and women's belongings scattered everywhere. They also found the portrait, which one of the looters took as a gift for the old woman. The ailing woman had no money with which to pay Dr. Poole, so she offered him the painting instead.
Poole became convinced the portrait was of Theodosia Burr Alston, and contacted members of her family, some of whom agreed, though Poole conceded "they cannot say positively if it was her." None of them had ever seen Theodosia in life. The only person who had actually known Theodosia that Poole contacted was Mary Alston Pringle, Theodosia's sister-in-law. To his disappointment, she could not recognize the painting as one of Theodosia.
In the years that followed, considerable publicity was given to this theory and in 1888 editor R.B. Creecy, of the Elizabeth City Economist, reported that he had interviewed a woman named Stella E.P. Drake, a descendent of the Burrs, who ha come to Elizabeth City to see the portrait. "We were startled by her close resemblance to the portrait in question," he said.
The following year Mrs. Drake wrote a letter to the Washington (DC) Post, recounting the details of her visit to the home of Dr. Poole. Describing her entrance into the Poole home, she said, "As I turned to go through the door I saw upon the wall above the mantelpiece a portrait of a young woman in white. That is the picture," I exclaimed. "I know it is, because it bears a strong resemblance to my sister."
The picture she saw was approximately 12" x 18" in size and painted on mahogany. It's been reproduced many times and is, together with accounts of pirate confessions and the story of Mrs. Mann, the strongest link in the thread of evidence concering Theodosia's fate. There is no record today of what Theo carried aboard the Patriot that fateful day. It certainly would be in keeping with her devotion to her father to have such a fine portrait in her possession as a gift to him.
A popular (though very improbable) local story in Alexandria, VA, suggests that Theodosia Burr Alston may have been the Mysterious Female Stranger who died in Alexandria at Gadsby's Tavern on October 14, 1816. She was buried in St. Paul's Cemetery with a gravestone inscription that begins: "To the memory of a / FEMALE STRANGER / whose mortal sufferings terminated / on the 14th day of October 1816 / Aged 23 years and 8 months."
A less romantic analysis of the known facts has led some scholars to conclude that the Patriot was probably wrecked by a storm off Cape Hatteras. Logbooks from the blockading British fleet report a severe storm which began off the Carolina coast in the afternoon of January 2, 1813, and continued into the next day. James L. Michie, an archaeologist from South Carolina, by studying its course has concluded that the Patriot was likely just north of Cape Hatteras when the storm was at its fiercest. "If the ship managed to escape this battering, which continued until midnight," he has said, "it then faced near hurricane-force winds in the early hours of Sunday. Given this knowledge, the Patriot probably sank between 6 p.m. Saturday [January 2] and 8 a.m. Sunday [January 3]."
The irony, however, is inescapable. Somewhere along this shore, where her father's nemesis had erected a lighthouse to save her, Theodosia Burr Alston lost her life on a stormy January night. And although we may never know exactly how that happened, a suicidal poet may have touched on why.
In 1894, a very young Robert Frost came to Kitty Hawk. Suffering from acute depression, he felt the need to get away from the pressure of life, and as many similar people do, he came to the Outer Banks. One night, he crossed over the Kitty Hawk beach and walked with a member of the local lifesaving crew on patrol. The patrolman told him Theo's story, and it moved him deeply. Years later, he would recount the experience and her tale in one of his lesser-known but moving poem, Kitty Hawk:
"Did I recollect how the wreckers wrecked Theodosia Burr off this very shore? 'Twas to punish her but her father more."