Thomas Jefferson vs. Willie Nelson March Madness: Bankruptcy Brackets

Welcome to the third round of March Madness Bankruptcy Brackets. In today’s video we’re going to find out which celebrity debtor will win the bankruptcy discharge regional and move on to the final four, where voters will decide who is the world’s greatest debtor.

In this match Thomas Jefferson the father of American democracy, will take on the popular Willie Nelson. Despite his unmatched achievements in the public arena, Thomas Jefferson could not control his spending impulse and owed his creditors an estimated One Hundred Thousand Dollars at his death in 1826. His idea to sell lottery tickets failed because he had overvalued the real estate from his great Monticello estate. His creditors were never paid. Willie Nelson teetered on the edge of bankruptcy after the IRS denied him millions of dollars in tax shelters and sent him a bill for over 16 million dollars. Nelson was able to bail himself out by selling off personal treasures, issuing a double album called “Who’ll Buy My Memories”, and suing his accounting firm.

To get to the Elite Eight Jefferson needed to win a compelling matchup against fellow icon Walt Disney and a tiebreaking struggle against baseball felon Lenny Dykstra. Willie Nelson sailed into this round by blowing out rock star David Crosby and convincingly defeating the hated Casey Anthony.

Willie Nelson had a much larger margin of victory in his early round matchups than Jefferson, who barely edged by his opponents. Nevertheless, the singer’s wins came on the strength of his fame and the high amount of his debt. In truth, Nelson got bad tax advice and was not responsible for his financial mess. More importantly, he paid it all off and continued his remarkable career.

Jefferson, on the other hand, lived beyond his means. Helped no doubt by his fame and influence, Jefferson was able to use credit to buy rare books, fine wines, slaves and real estate. The One hundred thousand dollars he owed on his death in 1826 would now be worth over two million dollars, a remarkable amount of debt for consumer spending. As a result, in this contest to determine the world’s greatest debtor, Jefferson has overcome the challenge from Willie Nelson and will move on to the final four as the champion of the Bankruptcy Discharge Regional.