Massey attended North Gwinnett High School in Georgia. He earned two letters in his high school career and was named 1st Team All-County and 1st Team All-Region as a senior. He was listed as the 18th best RHP in Georgia by Perfect Game, and chose to join Tulane in 2022.
As a freshman at Tulane, he made 15 appearances including 11 starts. He had an ERA of 5.03, tossing 68.0 innings with 52 strikeouts and 16 walks. He decided to transfer to Wake Forest following his freshman season.
As a sophomore in his first season with the Demon Deacons, Massey moved to the bullpen, making 27 appearances with just 1 start. He posted a 2.59 ERA in 41.2 innings of work, striking out 76 batters and walking just 16. He earned a starting job going into his junior year.
This season as a junior, Massey looks to continue his success in the ACC as a starter, and climb up draft boards into the early second round.