May graduated from Northwest High School in Justin, Texas. He was selected by the Los Angeles Dodgers in the third round of the 2016 Major League Baseball Draft. He was committed to play college baseball for the Texas Tech Red Raiders, but chose to sign with the Dodgers for a $1 million signing bonus, forgoing his commitment. After signing, May made his professional debut with the AZL Dodgers, and spent the whole season there, posting an 0-1 record with a 3.86 ERA in 30.1 innings pitched. In 2017, he played for both the Great Lakes Loons and the Rancho Cucamonga Quakes, compiling a combined 9-6 record, 3.63 ERA, and a 1.15 WHIP in 25 games between the two clubs. On August 3, he made his first start for the Tulsa Drillers of Double A going 3 2/3 innings giving up five earned runs. In 2018 for the Quakes he was selected to the post-season California League all-star team. On September 14, he started the Drillers title clinching playoff game where he allowed two runs in five innings. In 23 total starts between Rancho Cucamonga and Tulsa, he was 9-5 with a 3.39 ERA. May began 2019 with Tulsa. He was selected to the mid-season Texas League All-Star Game also the All-Star Futures Game. He was promoted to the AAA Oklahoma City Dodgers on June 27. May was called up to the majors on August 2, 2019, and made his major league debut for the Dodgers as the starting pitcher against the San Diego Padres. He pitched 5 innings, allowing four runs on nine hits with three strikeouts. On August 13, 2019, May picked up his first big league win against the Miami Marlins after pitching 5 innings, allowing one run on three hits with five strikeouts. He finished the season by appearing in 14 games for the Dodgers, with a 2–3 record, a 3.63 ERA and 32 strikeouts with only five walks. May was selected to start for the Dodgers on Opening Day in 2020 after Clayton Kershaw injured his back before the game. May became the youngest opening day starter for the Dodgers since Fernando Valenzuela in 1981.
Personal life
May is nicknamed "Gingergaard" after current New York Mets pitcher Noah Syndergaard due to similar player profile and appearance, as well as his red hair.