William ‘Fridge’ Perry
William “Fridge” Perry was a key figure on the legendary 1985 Chicago Bears Super Bowl-winning team. Alongside Walter Payton and Jim McMahon, Perry became one of the most recognizable (and beloved) members of the squad. Though just a rookie at the time, his impact was felt on both sides of the ball — primarily as a defensive tackle, but also as a fullback who rushed for three touchdowns that season.
Despite earning substantial income through contracts and endorsements, Perry ultimately lost his entire fortune. He even had to auction off his cherished 1985 Super Bowl ring. Perry’s unfortunate financial struggles mark a sad chapter for one of Chicago sports’ most adored players.
Warren Sapp
Warren Sapp was one of the most formidable talents of his generation. During his prime, Sapp dominated the field as a defensive tackle for the Tampa Bay Buccaneers. Over his nine seasons with the team, he earned four All-Pro selections, seven Pro Bowl nods, the 1999 AP Defensive Player of the Year award, and was instrumental in leading Tampa to a Super Bowl victory. Despite his Hall of Fame career and earning over $75 million, Sapp faced financial challenges after retirement, filing for bankruptcy in 2012. As reported by the Tampa Bay Times, he was $6.7 million in debt at the time.
Terrell Owens
Terrell Owens, another Hall of Fame talent, also faced financial struggles post-retirement. Over his 15-year career, Owens earned around $80 million, proving nearly unstoppable on the field. However, managing his finances after his playing days proved challenging. In a 2012 appearance on Dr. Phil, Owens revealed he was bankrupt. Later that year, he shared with GQ that he had lost nearly all his NFL earnings, attributing it to the downturn in the real estate market, poor investments, and substantial child support payments.
Dan Marino
Dan Marino is often regarded as the most talented quarterback to never win a Super Bowl. Unfortunately, he’s also gaining recognition for a less enviable reason. Playing in an era when NFL salaries were much lower, Marino sought to recoup some of his missed earnings. In 2012, he invested heavily in a company specializing in hologram images of deceased celebrities, often used in concerts. Marino reportedly purchased 16 million shares, but when the company went bankrupt, he lost an estimated $14 million in the process.
Lawrence Taylor
A three-time Defensive Player of the Year, eight-time All-Pro, two-time Super Bowl champ, and the 1986 MVP, Lawrence Taylor is regarded as the best defensive player of all-time — and some believe he is in the G.O.A.T. discussion. However, the Hall of Fame linebacker has had a turbulent ride post-football. According to TIME, Taylor once claimed he spent thousand of dollars per day on drugs. In addition to testing positive for cocaine twice while in the NFL, Taylor filed for bankruptcy in 1998 following a drug bust. From $50 million to bankrupt, Taylor lost it all.
