Thomas Jefferson
The future president was a hardworking farmer when he inherited massive debt from his father-in-law. He also was a generous soul who frequently lent money to friends who didn’t pay him back.
The combination of bad crops, bad loans and overspending left Thomas Jefferson drowning in red ink.
When bankruptcy briefly became a legal option, he took it — but when he died in 1826 he still had debts of $107,000, equivalent to between $1 million and $2 million today, according to his Monticello estate.
