20. William Perry
One of the most beloved players of his era, Perry’s life has been a rollercoaster. However, it is sadly plummeting off a cliff. He won a Super Bowl with the Chicago Bears and enjoyed a 10-season career in the NFL. A cultural phenomenon because of his massive size, Perry was a huge unit. He even appeared at WWE events and made many television appearances during his heyday. But massive problems soon arose.
Despite enjoying varied endorsement deals, Perry fell on hard times because of his lifestyle and frivolous spending. Meanwhile, he suffered from alcoholism, diabetes, and nerval inflammation. Sadly, Perry now resides in an assisted-living center and lives off of monthly social security checks because of debts to the IRS and medical bills. Furthermore, he sold his massive Super Bowl ring – the biggest ever – because he had no assets left.