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.[12] 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+1⁄3 innings allowing six hits and three earned runs while striking out six.[13]
In 2016, May 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.[14] In March 2017 an MRI revealed that May had a tear in his ulnar collateral ligament in his pitching elbow.[14] On March 21, it was revealed that May would undergo Tommy John surgery, therefore ending his 2017 season.[15]
May began the 2018 season on the 60-day disabled list. He was activated on June 6, and optioned to Triple-A.[16] For the Twins in 2019, May recorded a 2.94 ERA and 5–3 record with 79 strikeouts in 64+1⁄3 innings pitched.[17] In 2020, May had an ERA of 3.86 in 23+1⁄3 innings with 38 strikeouts.
New York Mets
On December 2, 2020, May signed a two-year contract worth $15.5 million with the New York Mets.[18] In 2021, May pitched in a career-high 68 games and posted a 7–3 record with a 3.59 ERA and 83 strikeouts in 62+2⁄3 innings.
On May 15, 2022, May was placed on the 60-day injured list with a stress reaction in the lower portion of his humerus.[19] He was activated on August 3, alongside Darin Ruf and Mychal Givens.[20]
Oakland Athletics
On December 16, 2022, May signed a one-year contract with the Oakland Athletics.[21] He made 49 appearances for the Athletics in 2023, registering a 3.28 ERA with 40 strikeouts and a career–high 21 saves in 46+2⁄3 innings pitched.[22] Following the season on October 16, 2023, May announced his retirement from baseball via Twitch, and in the process, spoke negatively about Athletics owner John Fisher and his plans to move the team to Las Vegas.[23]
Personal life
May has an avid interest in electronic music, previously using the pseudonym DJ HEYBEEF;[24][25][26] more recently, DJ MAZR,[27] 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."[28] May is a co-owner of Winston's Lab, an "Esports Lab" that focuses on measuring players' and teams' performance in Overwatch League (OWL).[29] In February 2017, May signed with Canadian professional esports organization, Luminosity Gaming as a streamer. May co-hosts the "May Contain Action" podcast along with Twitch Streamer Paul "actionjaxon" Jackson.[30]