Kenny Anderson – $60,000,000
Very few players over the past couple decades have sabotaged their lives (on and off the court) as miserably as Kenny Anderson. The High School All-American and college star’s road-to-ruin is like a bingo card for the typical issues you see in these stories.
There’s the collection of luxury cars (Porsche Carrera, Lexus, Mercedes, and a customized Range Rover), the poor business investment (a failed clothing line called “Kenny the Kid”), child support debts (seven kids from five different women), and legal issues (a DUI arrest in 2010 that forced his last employer — a Jewish High School — to let him go). It’s sad to see that his off-the-court exploits were in the news more often than his accomplishments in the NBA.