John Payne Todd

When the Madisons married in September 1794, James raised Dolley's two-year-old son Payne as his own and, by all accounts, was a dutiful, even indulgent, father. Payne attended a Catholic boarding school in Baltimore when the Madisons first moved to Washington, but during Madison's second term as president, 21-year-old Payne served as secretary to an official U.S. delegation to Europe. During these travels, Payne acquired many pieces of art that found a home at Montpelier.

However, his parents also received distressing reports of his irresponsible escapades.

Madison biographer Ralph Ketcham notes, "From this time on Todd was increasingly a financial drain and psychic strain on both his mother and stepfather"—drinking, gambling, and wandering in and out of the family circle.

Madison paid out more than $40,000 to Payne's creditors, at least half of this without Dolley's knowledge. Even so, Payne twice landed in debtors' prison—breaking his mother's heart.

Payne's debts and irresponsibility contributed to the dismantling of the formerly prosperous Montpelier. When widowed Dolley moved to Washington, Payne sold valuable possessions. He muddled the publication of James' papers and contested the provision in Dolley's will that left a bequest to her companion niece.

History remembers John Payne Todd as a man highly beloved by his doting mother—and hardly anyone else.