He moved to Adelaide, South Australia, in 2016 to attend Prince Alfred College.

[2][3] Bailey made his AFL debut in the ninety-three point loss to Richmond at the Melbourne Cricket Ground in round four of the 2018 season.

The following week, he kicked the match-winning goal after the siren against Collingwood at Marvel Stadium.

[6] Brisbane lost the game by a narrow margin, diminishing the impact of the stunning solo goal.

Bailey got his redemption by being a part of the Lions' 2024 premiership winning team, collecting 17 disposals and 7 marks in a 60 point victory over the Sydney Swans.