Wilt Chamberlain – Everything
In 1973, Wilt Chamberlain announced his retirement from the NBA. At the time, he was regarded as the finest player to ever enter the league. He appeared to try his hand at nearly every job available after retiring. He was looking for the ideal position, but he finally decided on that of a pitchman. In 1999, the basketball great died of heart failure. Although he is no longer living, his legacy lives on.
Gilbert Arenas – Analyst
No one expected Gilbert Arenas to be as good as he proved to be. In the 2001 NBA draft, he was the 31st pick. Despite this, he amassed a $163 million fortune before retiring. If you believed it meant he didn’t want to work again, you were incorrect. He must enjoy his profession. He may not have a traditional 9-to-5 job, but he does work for Complex as a sports commentator and YouTube sports show host.