May attended Kelso High School in Kelso, Washington. In his senior year, he led the Hilanders to a 25-2 win–loss record and a second-place finish at the 3A Washington Interscholastic Activities Association baseball championships. He had signed a letter of intent to play at the University of Washington.
May was named 3A State Player of the Year by the Washington State Baseball Coaches Association.
He graduated in 2008 as class valedictorian.
Philadelphia Phillies May was drafted by the Philadelphia Phillies in the fourth round of the 2008 Major League Baseball Draft. Prior to the 2011 season, May was the Phillies best prospect according to Baseball America That season, while pitching for the Clearwater Threshers, he went 10-8 with a 3.63 earned run average and 208 strikeouts in 151 innings. Prior to the 2012 season, May was the Phillies" best prospect according to Baseball America.
He was ranked 69th in all of baseball.
Minnesota Twins Personal May has an avid interest in electronic music under the pseudonym DJ Hey Beef.
On December 6, 2012 he was traded, along with Vance Worley, to the Minnesota Twins for Ben Revere. May was named to the 2014 All-Star Futures Game, but withdrew due to injury. May made his major league debut on August 9, 2014, against the Oakland Athletics. He had been pitching well for the Rochester Red Wings of the Class American Automobile Association International League, but lasted only two innings, throwing 28 of 63 pitches for strikes, walking seven, allowing four earned runs, and not striking out a batter. May got his first major league win on September 3, 2014 as the Twins beat the Chicago White Sox at home, 11-4. He pitched 5 innings allowing 6 hits and 3 earned runs while striking out 6.
