Curt Schilling
Despite his positive record as a pitcher for the Phillies and the Red Sox, Schilling filed bankruptcy in 2012. An injury pulled him off of the field in 2008, and he tried to create a conservative radio show to play in the interim. He was written off as a racist until 2016 when he revealed himself to be a huge advocate for Trump. He received money from the Trump campaign for spreading his message, and now he is worth about $1 million.