Born in Kapolei, Hawaii, Milton began his football career as a quarterback for UCF and Florida State.

He chose UCF because of new head coach Scott Frost, the former offensive coordinator of Heisman winning quarterback Marcus Mariota, whom Milton had idolized in high school.

[1] Milton started 10 games his freshman year leading the Knights to a 6–6 regular season record and an appearance in the Cure Bowl.

In his Sophomore year, Milton led the Knights to a 12–0 regular season record, winning the AAC[2] and eventually the Peach Bowl against the SEC runner-up Auburn Tigers.

[14] In an interview he gave for ESPN's Andrea Adelson as the second anniversary of his injury approached, Milton publicly revealed for the first time that he had to undergo two subsequent operations.

[17] On December 13, 2020, Milton announced that he would be transferring to Florida State University to play for coach Mike Norvell.

Milton completed 5 passes of 7 attempts for 48 yards and led the Seminoles back from a 10-point deficit late in the 4th quarter to tie the game and force overtime.

[20] Milton wore a custom gold helmet representing both UCF on one side and Florida State on the other, with a peace fingers sticker on the back representing the recent passing of friend and former UCF teammate Otis Anderson Jr.[21] On July 1, 2021, NCAA student-athletes were allowed to receive compensation for use of their name, image, and likeness (NIL) for the first time, and Milton was one of the first athletes to take advantage of the new rules.

He and Miami quarterback D'Eriq King became the co-founders and public faces of Dreamfield, a company specializing in booking live appearances for student-athletes.

[22] On May 23, 2023, Milton was hired by the University of Tennessee as an offensive analyst, reuniting with his former head coach Josh Heupel.