The money may flow fast in the NFL, but it can disappear even faster when bad decisions come into play. From trusting the wrong people to sinking millions into doomed business ventures, these athletes learned the hard way that being rich doesn’t make you financially savvy.
Whether it was a failed nightclub, a shady real estate deal, or just way too much faith in a “can’t-miss” opportunity, these 15 former NFL stars watched their fortunes crash and burn. Let their stories be a warning: not all investments are created equal.
15. Clinton Portis
The former Pro Bowl running back made millions on the field but lost much of it in a series of bad financial moves. He even considered confronting one of his financial advisors before ultimately filing for bankruptcy.
14. Bernie Kosar
Kosar was once one of the most reliable quarterbacks in the NFL, but his investments were anything but. A mix of bad real estate deals and generous loans to friends left him financially wrecked.
13. Vince Young
Young famously spent $5,000 a week at The Cheesecake Factory and invested in a now-defunct steakhouse chain. Despite a multimillion-dollar rookie contract, he filed for bankruptcy in 2014.
12. Chris McAlister
Once a Super Bowl-winning cornerback, McAlister reportedly ended up living with his parents. Poor financial planning and unwise investments dried up his wealth quickly after retirement.
11. Raghib “Rocket” Ismail
He was a college legend with an $18 million deal to match, but his post-career investments were a total bust. From a failed music label to an ill-fated phone card business, it all went up in smoke.
10. Jamal Lewis
After a successful NFL career, Lewis dove into trucking and other ventures—most of which didn’t pan out. He filed for bankruptcy with debts far exceeding his assets.
9. Tiki Barber
Barber retired early and tried to pivot to media and business, but it didn’t exactly go to plan. A messy personal life and failed ventures left his finances in rough shape.
8. Andre Rison
“Bad Moon,” Rison had a flashy lifestyle and the spending to match, but his financial investments were far less glamorous. Real estate issues and mismanagement left him broke.
7. Terrell Owens
TO made over $80 million during his career but admitted to losing nearly all of it. His troubles included bad financial advice, failed business ventures, and child support obligations.
6. Mark Brunell
A former Pro Bowl quarterback, Brunell invested heavily in real estate and Whataburger franchises. When the housing market crashed, so did his fortune.
5. Deuce McAllister
McAllister put his money into a Nissan dealership, which ended in lawsuits and bankruptcy. It was a tough blow after a solid NFL career.
4. Travis Henry
Henry had nine children with multiple women, which came with financial strain—but bad investments did the rest. A failed drug deal and other legal troubles didn’t help his bottom line.
3. Warren Sapp
Sapp made over $80 million in the NFL but filed for bankruptcy in 2012. He blamed everything from a bad condo investment to owing friends and family money.
Read more: 10 Athletes Who Invested in Businesses That Crashed Fast
2. Lawrence Taylor
LT’s money problems stemmed from both poor financial decisions and legal troubles. Several failed investments only deepened his post-NFL struggles.
Read more: 15 NFL Legends Who Tried Business Ventures That Totally Flopped
1. Lenny Dykstra (NFL cameo as an investor advisor)
Okay, technically not an NFL player—but several NFL athletes trusted Dykstra with their money, and it didn’t end well. His schemes and shady ventures dragged down a few football fortunes with him.
Read more: 14 Former NFL Stars Who Got Humbled by Life After Football
