Despite being born into money and marrying into it twice, debt continually shadowed John Tyler. Forced to put up appearances and entertain to advance his political aspirations, he usually lived beyond his means. He tended to be generous with friends and often made bad loans, and his fourteen children meant a constant blizzard of schooling, grocery, medical and wedding bills. Many of his political positions did not pay well, and farming was always rife with uncertainties, leaving the former President to die in debt.

Despite his financial situation, he did his best to provide well for his children, even if it required nepotism to do so. His eldest son, also named John, was given a salaried job as a press secretary while Tyler was President, but he drank excessively and proved unreliable. The President had to fire his son toward the end of his term. Tyler, born during the presidency of George Washington, fathered his last child at age seventy, and the last of his offspring would live into the Truman presidency.

During Tyler's lifetime, Washington, D.C., was a swampy, disease-ridden place. Forced to live there while in Congress, Tyler preferred to leave his wife and children at the plantation in Virginia. Only when he became President did the family join him in the capital.

Tyler found little to be apologetic about regarding the seventy slaves he owned. His first wife, Letitia, expressed reservations about the growing abolitionist movement. His second wife, Julia, had few qualms about it. From all accounts, John Tyler was a decent slaveowner. He refused to allow overseers to whip his slaves or split up their families; privately squeamish about slavery, he never attended an auction. On one occasion, Tyler was forced to sell a favorite slave to finance a move to Washington, and he was deeply distressed when he did so. He was a compassionate master but an owner of other humans nonetheless.