On New Year’s Eve, 1812, Theodosia Burr Alston, First Lady of South Carolina and daughter of former U.S. Vice-President Aaron Burr, boarded a ship bound for New York City and was never seen alive again. More than 50 years later, in Nag’s Head, North Carolina, an old woman gave a doctor a painting, as payment for medical services, that the doctor came to believe was a portrait of Theodosia. But was it, and if so, how did it get there? These two unsolved mysteries bookend the unusual life and personality of Theodosia Burr Alston, an educated, talented woman, outspoken feminist, who was utterly devoted to her father Aaron Burr, the “gadfly” of the Early Republic, a controversial man accused of murder and treason, who ultimately lost both of the women he held most dear in his life.

In drilling down into the twin mysteries of Theodosia Burr, historian Sean Munger sets the stage with colorful examples from her life and her father’s. In this episode you’ll not only meet various members of the Burr family, but you’ll encounter coastal pirates and unscrupulous beachcombers, two unidentified women buried in different places along the Atlantic coast who may or may not have been the real Theodosia, and follow in the footsteps of New England maritime historian Edward Rowe Snow as he tries (not entirely successfully) to solve the mystery in the 1940s. You can be the judge of whether the woman in the “Nag’s Head Portrait”—she is pictured on the far right of the image collage header for Second Decade podcast—really is Theodosia Burr Alston.

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