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. After the season, he won the Paul Owens Award, which is awarded to the Phillies best minor league pitcher. Prior to the 2012 season, May was the Phillies' best prospect according to Baseball America. He was ranked 69th in all of baseball.
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 AAAInternational 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 Soxat home, 11-4. He pitched 5.1 innings allowing 6 hits and 3 earned runs while striking out 6. In 2016, he was 2-2 with a 5.27 ERA as a reliever, before his season ended with a back injury that was diagnosed as a stress fracture. In March 2017 an MRI revealed that May had a tear in his ulnar collateral ligament in his pitching elbow. On March 21, it was revealed that May would undergo Tommy John surgery, therefore ending his 2017 season. May began the 2018 season on the 60-day disabled list. He was activated on June 6, and optioned to Triple-A.
Personal life
May has an avid interest in electronic music, previously using the pseudonym DJ HEYBEEF; more recently, DJ MAZR, and streams on Twitch. May described himself as "a partnered Twitch Streamer, a DJ, a Social Media connoisseur, an esports Entrepreneur, a gaming tournament organizer and commentator, and obviously an exceptional writer." May is a co-owner of Winston's Lab, an "Esports Lab" that focuses on measuring players' and teams' performance in Overwatch League. In February 2017, May signed with Canadian professional esports organization, Luminosity Gaming as a streamer.