Vin Baker: Career Earnings, $100 million
You want a riches-to-rags story? In a 25-year span, Vin Baker went from an NBA All-Star with a $100 million contract, to completely broke and training to be a manager at Starbucks. The four-time All Star developed a serious drinking problem during his playing days, and the addiction would eventually cost him his NBA career.
As far as the money he earned? It’s a combination of the usual suspects: some bad investments, but mostly lavish expenditures on suits, cars, shoes, and bankrolling his entourage (who would often rack up bills over $10,000 for a single meal). In 2008, Baker lost his 10,000 square-foot Connecticut mansion to foreclosure.