Myles grew up in Tallahassee, Florida and attended Lincoln High School. He committed to Florida State in 2021. In 2023, he was named the All-Big Bend Player of the Year, hitting .389 with 28 hits and 10 home runs as a junior at Lincoln.[1] Bailey was ranked the no. 37 overall player and no. 1 first baseman in the 2024 recruiting class by Perfect Game.[2] Before his freshman year at Florida State, he was drafted in the 20th round by the Chicago White Sox during the 2024 Major League Baseball draft.[3] He decided to forgo the draft and sign with the Seminoles.
In Bailey's freshman season as a Seminole, he started 56 games as a first baseman hitting .327 with 66 hits, 11 doubles, and 56 RBI. He also had 19 home runs, which was the second highest in the Atlantic Coast Conference.[4] Bailey received post-season honors when he was recognized on the ACC All-Freshman Team and named a Baseball America All-American. He was also invited to the 2025 USA Baseball Collegiate National Team Training Camp in Cary, North Carolina.[4]
In December 2025, Bailey was recognized as a top prospect on MLB Pipeline's top 100 Draft Prospects for 2026.[5]