Roger Stabauch – $600 Million

Despite being drafted in 1964, Captain America, as Roger Staubach was nicknamed, didn’t begin his professional career until 1969 after completing his military service. He later rose to prominence during his 11-season career with the Dallas Cowboys. As the team’s starting quarterback, he quickly made an impact, leading them to their first Super Bowl triumph in the early ’70s.

However, concerns over his health led to his early retirement in 1979. But after leaving football, Staubach founded a highly successful commercial real estate company that sold for $613 million in 2008. Today, he is worth a tremendous $600 million and even co-owns a NASCAR team.