From owning slaves to fathering illegitimate families with said slaves, Jefferson has grown into one of the most debated public figures of the Revolutionary era. But Jefferson's biggest headaches throughout his own lifetime probably weren't attacks of moral conscience. Instead, they seemed to be the quite crushing debt that he incurred from a boatload of sources.
For one, Jefferson might not have been entirely fiscally responsible; he spent a great deal on luxuries like wine and household amenities. It also didn't help that his father-in-law, John Wayles, transferred a huge debt burden to Jefferson after Wayles' 1774 death. To make matters worse, after endorsing a $20,000 note for a friend in 1818, the friend died and left the unpaid amount (about $345,000 in today's cash) in Jefferson's name [sources: Monticello, Sahr].
And let's not forget that Jefferson ran a farm that wasn't exactly a cash cow. He had land, he had slaves, but he didn't have a steady flow of ready income [source: Monticello]. All this resulted in the sale of much of his land and property, including Monticello, after his death. His nephew cited a debt of $107,000 after Jefferson's passing, equivalent to one or two million dollars today [source: Monticello].