There are very few players in MLB history with crossover legacies with both the Boston Red Sox and the New York Yankees. Damon was a World Series champion with the Red Sox on their curse-breaking 2004 team. Damon came to Boston from Oakland for the 2002 season and spent four years with the Red Sox. In those days, Damon had the long hair and the beard that made him an iconic player for the Red Sox. He's now 52 years old, having finished his MLB career in 2012, threading the narrow needle of being a legend for both the Red Sox and the Yankees.