He pitched for the Cape Cod Baseball League’s Yarmouth-Dennis Red Sox in 2009 and was named MVP of the all-star game. He was drafted again at the 2010 MLB Draft #13 by the Chicago White Sox and made his professional debut the same year. Sale has pitched for the White Sox for his entire MLB career. He has been a three time All-Star from 2012 to 2014 and was named American League Pitcher of the Month in May 2012. In 2013 he signed a five year deal worth $32 million with the White Sox.