Jason Williams Made $63,000,000
A late-bloomer who made his only All-Star Game at 30 and had his career end due to injury at 31, Jayson Williams could very well have been the next Charles Barkley as a TV analyst. He did work for NBC for a while but lost his job in 2002 after accidentally discharging his firearm and hitting his limo driver.
Despite his personal problems, Williams always was a generous guy and was known around New York for his $500 tips. All of that added up and contributed to his defense lawyer revealing that Williams was nearly bankrupt during his 2010 court case, despite making over $63 million.
After being released from prison in 2012, Williams turned his life around and now operates the Rebound Institute, a recovery and wellness center in South Florida.
Joe Smith Made $61,000,000+
An ordinary name with an extraordinary career, Joe Smith was the first overall pick in 1995 and would later play for 12 NBA teams, which ties the all-time record. He never lived up to the hype of being the first pick, but stuck around long enough to play for 16 seasons and accumulate over $61 million. But playing for so many teams is what did Smith in as he says he bought a new home every time he joined a new team.
Smith revealed he was broke in 2018, but another No. 1 pick from a different sport lent a helping hand. Former MLB star Alex Rodriguez featured Smith in his CNBC show, “Back in the Game,” which he helps former athletes get back on solid financial footing. With the help of A-Rod and a financial adviser, they devised a plan that should help Smith overcome his $157,000 debt by paying off 30 percent each year, enabling Smith to become debt-free by 2022.