# The 15 Biggest Sports Fortunes Ever Lost

> Enormous contracts, catastrophic decisions, and a bankruptcy filing at the end of it. The money went somewhere.

*By YPB Team · Published August 2, 2026 · https://youpick.best/ranking/the-15-biggest-sports-fortunes-ever-lost*

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## Current results (0 votes)

1. **Mike Tyson**
   Earned around $400m in the ring, filed for bankruptcy in 2003.
2. **Allen Iverson**
   Over $200m in career earnings and endorsements, gone.
3. **Antoine Walker**
   $108m in NBA salary and a 2010 bankruptcy filing.
4. **Evander Holyfield**
   Four heavyweight titles, a foreclosed 109-room house.
5. **Vince Young**
   A $26m rookie deal spent before the career ended.
6. **Diego Maradona**
   Years of Italian tax debt that outlived him.
7. **Boris Becker**
   Three Wimbledon titles, then a bankruptcy conviction.
8. **Lenny Dykstra**
   From baseball to a car wash empire to Chapter 11.
9. **Scottie Pippen**
   Six rings and a string of bad investments.
10. **Dennis Rodman**
   Five rings and repeated public money troubles.
11. **Terrell Owens**
   $80m in NFL earnings and four failed entities.
12. **Bjorn Borg**
   Eleven majors, then a bankrupt clothing line.
13. **Michael Vick**
   A $130m contract and a 2008 bankruptcy filing.
14. **Warren Sapp**
   A Hall of Fame career and a 2012 filing.
15. **Latrell Sprewell**
   Turned down $21m, later lost the house and the yacht.

Tags: sports, all-time, money