[4][5] The Oakland Athletics selected Bailey in the sixth round of the 2016 Major League Baseball draft.

[6] He signed with Oakland and spent his first professional season with both the AZL Athletics and the Vermont Lake Monsters, posting a combined 3–1 record and 2.93 ERA in 12 games between both teams.

In 2017, Bailey spent time with the Beloit Snappers and the Stockton Ports, pitching to a 3–2 record and 3.26 ERA in 24 total games.

[8] In 2018, Bailey split the season between the Buies Creek Astros and the Corpus Christi Hooks, accumulating a 6–8 record with a 2.80 ERA in 121 innings.

[11] Bailey competed for a spot on Baltimore's Opening Day roster in spring training, but was returned to the Astros' organization on March 6.