Bailey was born on May 28, 1997[2] in Jacksonville, Florida. He went to William M. Raines High School before attending Iowa State University.[3][4][5][6][7] He was a 3-star recruit and choose Iowa State over offers from Tennessee, Florida, Louisville, and Virginia Tech.[8] In his first season he played in 12 games,[9] starting 7, and was named Freshmen All-America.[8] The next season he was an Honorable Mention All Big-12, with 7 sacks.[8] He played in 13 games for the second straight year in 2018.[8] He had 46 tackles to lead all Iowa State defensive linemen.[8] He was named Second-team All Big-12 and on the Ted Hendricks award watchlist.[8] In 2019, he played in 4 games before being a medical redshirt.[8] In 2020, he started all 12 games, and was named First-team All-American by two selectors.[8] He was also named First-team All-Big-12.[8]
