9. Chauncey Billups (Estimated net worth: $45 million)
Chauncey Billups won an NBA title with the Detroit Pistons in 2004 and was also named the Finals MVP in the series. Before his stellar accomplishments, he played with four different teams. His No. 1 jersey was retired by the Pistons and his No. 4 jersey was retired by the University of Colorado. He played in the league for 18 years.
Mr. Big Shot made it big in the business arena by being a franchisee. He partnered with former NBA player Junior Bridgeman and formed BB St. Louis LLC. Through the company, they bought 30 Wendy’s restaurants. When not managing his restaurants, Billups is a TV analyst for ESPN.