Cal Ripken, Jr.

Retired: 2001

Career Earnings: $30.5 million

Est. Net Worth: $75 million

Nicknamed “Iron Man,” Cal Ripken Jr. is a former MLB player who played twenty-one seasons in the MLB—all for the Boston Orioles—from 1985 until 2001. Ripken was named an All-Star nineteen times and he was the AL MVP twice. Ripken still holds the record for the most games played in a row: an incredible 2,632 games.

Now retired, Cal hasn’t shown any signs of taking it easy. He’s a best-selling author and the founder and CEO of Ripken Baseball, Inc. Ripken Baseball, Inc. owns three minor league baseball teams. Ripken lives in Annapolis, Maryland with his wife, Laura, a circuit court judge.