He played college baseball at North Carolina State University and was selected 13th overall by the Giants in the first round of the 2020 MLB draft.

Bailey attended Wesleyan Christian Academy ('17) in High Point, North Carolina, where he played catcher for the baseball team.

[3] As a sophomore in 2019, Bailey batted .288/.390/.513 with three triples (eighth in the ACC) and 10 home runs alongside a .989 fielding percentage.

[2] He hit six home runs (fourth in the ACC), 20 RBIs (second), and 17 walks (third) over 17 games before the college baseball season was cut short due to the COVID-19 pandemic.

[16] Over 47 games with San Jose to finish the season, Bailey slashed .322/.416/.531 with seven home runs, 24 RBIs, and 16 doubles, and caught 48% of attempted base-stealers.

[25] On May 21, 2023, Bailey hit his first major league home run in a 7–5 win over the Miami Marlins.

On August 1, 2023, Bailey – after entering the prior inning as a defensive replacement – ended a game with the a walk-off pick-off from his knees, catching Diamondback Geraldo Perdomo on first base with two outs in the ninth inning in a one-run game, with the fastest pop time (1.39 seconds) to first base on a successful pickoff throw in the Statcast era (since 2015).