The 15 Biggest Sports Fortunes Ever Lost

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

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.