For every touchdown scored or Super Bowl won, there’s an off-field gamble that didn’t quite pan out. While some NFL legends have successfully transitioned to the boardroom, others learned the hard way that business success isn’t guaranteed, no matter how many Pro Bowls you’ve made.
From frozen foods to failed car washes, these 15 former NFL stars launched ventures that either lost steam, lost money, or just plain didn’t make sense. Here’s a look at the business moves that didn’t live up to the hype.
15. Clinton Portis

Clinton Portis invested heavily with a financial advisor who turned out to be, let’s say, not the most qualified. His business efforts ended with lawsuits, bankruptcy filings, and a reminder that flashy suits don’t equal financial smarts.
14. Deion Sanders

Prime Time tried launching a charter school network, and it didn’t exactly go according to plan. The schools faced financial issues, mismanagement allegations, and ultimately shut down.
13. Vince Young

Vince Young opened a steakhouse in Houston, and it shut down faster than his NFL comeback attempts. Legal battles and unpaid bills piled up, turning his business dream into a cautionary tale.
12. Bernie Kosar

Bernie Kosar tried everything from restaurants to car dealerships, but most of it ended in financial ruin. He even declared bankruptcy, with over $18 million in debt and a business portfolio that looked more like a clearance rack.
11. Jamal Lewis

Jamal Lewis got into trucking and real estate development, but the ventures hit a wall. He ended up filing for bankruptcy after his post-football investments couldn’t keep up with the bills.
10. Terrell Owens

T.O. didn’t just drop passes—he dropped millions on bad investments and shady financial advisors. His business ventures were so unsuccessful, he ended up going public about being nearly broke.
9. Chris McAlister

Chris McAlister once had a $50 million NFL contract, but post-retirement life hit him hard. He admitted to being broke and living with his parents after a string of failed business decisions and financial missteps.
8. Michael Vick

Vick’s name was once tied to a sporting goods line and other endorsement ventures, but they all crumbled under the weight of his legal troubles. His off-field business potential never had a real chance to grow.
7. Andre Rison

“Bad Moon” Rison lived up to his nickname with some wildly reckless spending and terrible investments. One of his worst moves? Backing a music label that never took off and burned through his cash.
6. Warren Sapp

Warren Sapp was a beast on the field, but his business choices were a mess. After investing in failed real estate deals and blowing millions, he filed for bankruptcy, claiming he couldn’t even afford a pair of shoes.
5. Fred Taylor

Fred Taylor lost millions through shady financial management and tried launching a marketing firm that didn’t take off. He’s since spoken openly about the hard lessons learned from putting trust in the wrong people.
4. Ray Rice

After his NFL career ended, Rice made attempts to rebrand through business ventures, including trying to get into sports management. But public backlash and lack of interest from partners shut those doors quickly.
3. Mark Brunell

Brunell was once one of the NFL’s top quarterbacks—and one of its worst businessmen. He invested in fast food franchises, real estate, and a chain of Whataburgers, only to end up filing for bankruptcy.
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2. Lawrence Taylor

LT’s post-career life has been filled with legal troubles and business stumbles. From failed ventures to bad endorsements, his financial decisions have been as chaotic as his playing style.
Read More: 14 Former NFL Stars Who Got Humbled by Life After Football
1. Johnny Unitas

Yes, even Johnny U took a shot at business and missed. His electronics company went under in spectacular fashion, leaving him in deep debt despite his iconic status in the sport.
Read More: 10 Times NFL Stars Filed For Bankruptcy