May was drafted by the Cincinnati Reds in the 39th round of the 2010 Major League Baseball Draft out of Lakota West High School in West Chester, Ohio. He did not sign and played college baseball at Coastal Carolina University. May was then drafted by the Chicago White Sox in the third round of the 2013 Major League Baseball Draft. He made his professional debut with the Great Falls Voyagers and was later promoted to the Kannapolis Intimidators. After the season, he played for the Sydney Blue Sox of the Australian Baseball League. May played 2014 with the Winston-Salem Dash, 2015 with the Double-A Birmingham Barons and 2016 with the Triple-A Charlotte Knights. The White Sox added him to their 40-man roster after the 2016 season.\n', '

On March 28, 2017, May was named the White Sox\' starting center fielder to open the season. However, he only appeared in 15 games for the team during the season, batting 2-36 with 3 RBIs and 3 walks. He played the majority of the year with the Triple-A Charlotte Knights. \n', '

On January 11, 2018, May was designated for assignment in order to make room for newly acquired pitcher Miguel Gonzalez on the 40-man roster. He appeared in 81 games for Charlotte before he was released from the organization on July 28, 2018. \n', '

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