Bailey attended Billy Ryan High School in Denton, Texas. Over his high school career, he rushed for 4,026 yards and 51 touchdowns. He committed to play at Louisiana.
As a freshman, he rushed just 10 times in his five games played. As a sophomore, his carries increased drastically as he rushed 102 times for 642 yards in 11 games played. He then entered the transfer portal and chose to attend TCU.
In his first season with TCU in 2022, Bailey serve as the third back in a committee, and did not see much playing time only rushing for 250 yards on 31 carries. However, he took the starting role for the Horned Frogs in 2023 and had a breakout season heading into the draft. He rushed for 1,209 yards on 223 carries, making his case for a draft pick this year.