1. Michelle Damon (Married to Johnny Damon)
As the original “caveman,” Johnny Damon has been enjoying retired life for the past few years, alongside his smoking hot wife, Michelle Damon. They’ve been married since 2004, when Damon was a part of that historically magical World Series championship win by his Boston Red Sox. The Damon’s probably spend most of their time chasing after their herd of children, which grew to a total of six with the birth of another son this year. From 2001 – 2009, Damon earned more than $80 million from the Boston Red Sox and New York Yankees. Not a bad nest egg to head into retirement with.