Education
Dewees attended Crystal River High School and enrolled at the University of North Florida to play college baseball for the North Florida Ospreys.
Dewees attended Crystal River High School and enrolled at the University of North Florida to play college baseball for the North Florida Ospreys.
He played college baseball for the North Florida Ospreys of the University of North Florida. He had a.347 batting average as a freshman, and was named a Freshman All-American. He batted.319 as a sophomore.
He played collegiate summer baseball in the Northwoods League after his freshman year and the Cape Cod Baseball League after his sophomore year.
Expected to be an early selection in the 2015 MLB Draft, the Chicago Cubs selected Dewees in the second round, with the 47th overall selection, of the draft. He signed with the Cubs, receiving a $1.7 million signing bonus, and made his professional debut for the Eugene Emeralds of the Class A-Short Season Northwest League.