John Payne Todd

John Payne Todd was born on February 29, 1792, in Philadelphia, Pennsylvania. He was the son of Dolley and her first husband, John Todd, Jr. Dolley also had another son named William Temple Todd, born in July 1793. During the yellow fever epidemic in Philadelphia during the late summer of 1793, both John Todd, Jr., and William Temple Todd succumbed to the fever leaving behind Dolley and her eldest infant son John Payne Todd.

When Dolley Payne Todd married James Madison in September 1794, her two-year-old son was adopted by Madison. Since it was to be that Dolley and James had no children of their own, the motherly and fatherly affections of both rested upon their only son John Payne. During the time that the Madisons resided in Washington, D.C., their son was schooled in a Catholic boarding school in Baltimore until 1812. From April 1813 to September 1815, John Payne Todd accompanied the official delegation from the United States sent to meet with the British in Ghent, Belgium. He traveled though Russia, France, Belgium, England, and the Netherlands, and it was during these travels that he acquired many pieces of art that were sent back to his parents and hung in the rooms and halls of Montpelier.  It was also during this time that John Payne Todd began to show signs of the indolent fop that he would later become. Historian and Madison biographer Ralph Ketcham writes of John Payne Todd:

"He had become a classic example of the young American, warned of by Franklin and Jefferson, who was so dazzled by the courtly graces of Europe that he became unfit for useful life in his own country. From this time [1813-1815] on Todd was increasingly a financial drain and psychic strain on both his mother and stepfather."

— Ketcham 1990: 601