Athletes are often surrounded by big paychecks, hype, and high-risk opportunities, and sometimes that cocktail leads to some regrettable business decisions. From restaurants that never made it past the soft opening to tech startups that fizzled faster than a viral trend, even the most prominent stars can end up backing the wrong horse.
The problem? Fame doesn’t always translate to financial foresight. These athletes may have ruled the court, field, or ring, but their investments didn’t exactly stick the landing regarding business.
10. Curt Schilling
The former MLB pitcher poured millions into a video game company that flamed out epically. Despite the initial buzz, the business quickly turned into a financial nightmare.
9. Vince Young
Once a star quarterback, Vince invested in a steakhouse that closed faster than his NFL career faded. It was an expensive reminder that meat and money don’t always mix.
8. Lenny Dykstra
Dykstra fancied himself a financial mogul post-baseball, but his magazine venture tanked almost immediately. Being a gritty outfielder doesn’t mean you’re ready for Wall Street.
7. Terrell Owens
T.O. invested in a chain of bingo halls that never really got off the ground. It was not precisely the touchdown investment he had been hoping for.
6. Mark Brunell
The former quarterback was part of a failed real estate development that left him in serious financial trouble. Location, location, liquidation.
5. Evander Holyfield
Holyfield once backed a record label that never escaped the amateur rounds. The music business threw more punches than his opponents ever did.
4. Antoine Walker
Walker invested in various businesses, including a clothing line and real estate deals that flopped hard. The losses piled up faster than his NBA turnovers.
3. Allen Iverson
Iverson reportedly invested in a string of ventures that vanished quicker than his infamous crossover. The only thing breaking ankles here was his bank account.
Read More: The Winning Playbook: 10 Sports Stars Who Excelled in Business Ventures
2. Michael Vick
Vick invested in a high-end clothing line that disappeared faster than his post-prison comeback. It was all flash and no follow-through.
Read More: 15 Millionaire Athletes Who Fumbled the Bag
1. Shaquille O’Neal
Yes, even Shaq isn’t immune. He once backed a video-on-demand service that crashed within months. It turns out that not everything he touches turns to gold; it just turns to most things.
Read More: 20 Shockingly Bad Investments That Crashed and Burned
