Dolley Madison’s Heartache: Payne Todd

Dolley and James Madison had no children of their own. John Payne Todd was the son of her first marriage.  

Dolley and James Madison Are Wed 

The Widow Todd, as she was then called, was helping manage her mother’s Philadelphia boarding house, following the early death of her husband in a yellow fever epidemic. Left with a two-year-old son, she had moved back with her mother.

Dolley Payne Todd was a twenty-five year old widow when she met Congressman James Madison. He was forty-three, and had earned his reputation as “The Great Little Madison,” after he helped shepherd the Constitution of the new United States of America through a fractious convention.

Dolley by Gilbert Stuart

Dolley Madison was a 25-year-old with a two-year-old son when she met and married James Madison, eighteen years her senior.

The shy Madison fell deeply in love with the vivacious young widow, who was earning her own reputation as the most delightful hostess in Philadelphia. It would be a quiet courtship, given the fact that Madison was a reticent man by nature, due in part to his small physical stature. The fact that Dolley was a recent widow was another reason for their discretion: the conventions of mourning need to be upheld. Madison, however, did the one thing he knew would touch Dolley’s heart: when he came to visit, he brought toys or treats for little Payne. Dolley knew he would be a kind protector for her little boy.

James Madison the Stepfather

James Madison, from the beginning, was more like an indulgent grandfather than father. Payne was Dolleys’ son, not his. And after an epidemic that claimed her husband and infant son, he was all Dolley had.

As years passed, with no brothers or sisters to join Payne, Dolley Madison became even more lenient. From the start, Payne was a lazy child, much happier shooting, riding and playing at Montpelier, the Madison plantation, than studying.  His stepfather spared no expense engaging tutors for the recalcitrant student. For a while, he even endeavored to tutor Payne himself. It was not successful.

Educating Payne Todd

idealized madison

James Madison was more of a grandfather than father figure to young Payne Todd. He spent fortunes trying to help his stepson – and paying his debts.

Finally, as the lad approached adolescence with little progress made in his formal education, Madison decided that Payne might benefit in an environment of his peers. He sent his stepson to  St. Paul’s Academy in Baltimore, hoping that Payne would acquit himself well enough to enroll in the College of New Jersey, Madison’s alma mater in Princeton.  It would not happen.

Payne Todd had inherited his mother’s good looks, and even better, her charm and engaging personality. The peer group that Madison had anticipated accepted Payne readily. He was delightful company. But rather than providing a good influence, Payne discovered companions who would teach him habits that would become lifelong vices: wine, women – and wagering. Young Payne Todd was a disappointment scholastically.

Payne Todd, Diplomat


The only known likeness of John Payne Todd. He had his mother’s good looks and abundant social charm, but he was addicted to drink and gambling.

At a loss for how to channel his energies more profitably, a now-president President Madison sent his twenty-year-old stepson to St. Petersburg, Russia, as part a special American delegation – to serve as a clerk or secretary.

Courtiers in Tsarist Russia had little knowledge or understanding of a democratic social system. The nobility indulged the President’s stepson as they would a Crown Prince. His drinking and gambling were encouraged. So was his appetite for high living. He routinely ran into great debt.

Once again, Payne Todd was a failure in any efforts to channel him into a responsible life or vocation. About the only thing he could do, was to send some artwork back to his parents – and write to his stepfather for financial help. He seldom wrote to his mother. Madison, who loved his wife dearly, usually sold off acreage to pay Payne’s obligations. Most of the time, he did so without informing his wife. He knew it would break her heart.

Payne Todd Spirals Into Dissipation

Both Madisons tried desperately to reform Dolley’s wayward son.   His core was not that of a vicious person, rather of a person addicted to vicious habits. They introduced Payne to several eligible young women, hoping that marriage might stimulate the still-young man to responsibility. Nothing seemed to work. Payne preferred the lower-classes.

The Madisons even provided a modest plantation for Payne – a place of his own, which he might manage as a means of self-support. Like everything else, that failed as well. Payne’s attraction to the gambling tables was doom to the plantation. He would even spend time in debtor’s prison on two separate occasions.

Dolley Madison, Her Son, And Congress

payne's grave

Payne died of the effects of his dissipation a few years after his mother died. Dolley’s death and funeral were mourned by all. Payne’s death went unnoticed.

When James Madison died at eight-five, Dolley was nearly seventy.   Payne, by this time, was well into his forties. Montpelier, the Madison plantation in Virginia, had become too much for the former First Lady to maintain. Indeed, it had become too much for the elderly Madison to maintain, and was actively failing largely due to Payne Todd’s improvidence.   Dolley was only partially aware of the extent of the funds expended to pay Payne’s debts over the years.

Perhaps in desperation, Dolley solicited her son to help sell the plantation – and also to help sell Madison’s papers, which the elderly Founding Father had left to her as security for her old age. Payne was a failure at that as well.   His dissipation was well known to everyone – except perhaps, to his mother, who never stopped loving him or hoping that he would change. The doting mother readily admitted that she had spoiled her son, but always said, “His heart is good, and he means no harm.”   When Congress finally agreed to purchase the Madison papers, they arranged payment as an annuity, so that Payne could not further bankrupt his already impoverished mother. He tried, nevertheless to beg, borrow and connive.   Payne Todd died in a pauper’s grave.


Allgor, Catherine – A Perfect Union: Dolley Madison and the Creation of the American Nation – 2006 Henry Holt and Company

Angelo, Bonnie, First Families: The Impact of the White House on their Lives – 2005, HarperCollins


About Feather Schwartz Foster

Feather Schwartz Foster is an author-historian who has made more than 500 appearances discussing presidential history. She teaches adult education at the Christopher Wren Association (affiliated with William and; Mary College), and adult Education programs at Christopher Newport University. She has been a guest on the C-SPAN "First Ladies" program. She has written five books.
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2 Responses to Dolley Madison’s Heartache: Payne Todd

  1. Pingback: In Intimate Tour of Montpelier with James and Dolley Madison - Digital Yarbs

  2. Pingback: An Intimate Tour of Montpelier with James and Dolley Madison - Digital Yarbs

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