Whitson attended
Chipley High School in
Chipley, Florida. As a senior, Whitson pitched to a 0.62
earned run average (ERA) and recorded 123
strikeouts in 55
innings pitched.
Baseball America ranked Whitson the third best high school prospect in the United States. He played in the Aflac
All-America game and pitched in the Pan American Junior Baseball Championship. The
San Diego Padres selected Whitson in the first round, with the ninth overall selection, of the
2010 Major League Baseball draft. Despite the Padres offering Whitson a
signing bonus of $2.1 million, he opted not to sign, surprising the Padres front office. Whitson reportedly asked for $2.7 million, but stated that he felt he was not ready for the challenge of
minor league baseball. Whitson enrolled at the
University of Florida, and joined the
Florida Gators baseball team, pitching in the
Southeastern Conference. As a freshman, Whitson pitched to an 8–1
win–loss record, with a 2.40 ERA and 92 strikeouts in 97 innings. He was named a Freshman
All-American by
Collegiate Baseball Newspaper. Whitson pitched to a 4–0 with a 3.51 ERA in 2012 as a sophomore. After the 2012 season, he played
collegiate summer baseball with the
Orleans Firebirds of the
Cape Cod Baseball League. He missed the entire 2013 season due to a shoulder injury that required surgery, which was performed by Dr.
James Andrews. His
labrum and
rotator cuff were undamaged. The
Washington Nationals selected Whitson in the 37th round, with the 1,126th overall selection, in the
2013 MLB draft. Whitson did not sign with the Nationals, returning to college for his senior year. Whitson had a 3.86 ERA with the Gators in 2014, making nine starts and five relief appearances. The
Boston Red Sox selected Whitson in the 11th round of the
2014 MLB draft. He signed on June 20. He pitched for the
Lowell Spinners of the
Low–A New York–Penn League in 2014. ==Personal==