Bailey grew up in San Diego with a single mother who worked "two, sometimes three jobs" and initially attended Helix High School in La Mesa before switching to Olympian High School in Chula Vista, where he could live with his godmother during the week.

In his two seasons, and 25 games played at Eastern Michigan, Bailey racked up 1,746 receiving yards with 114 receptions and 16 touchdowns.

He played in 13 games his junior year in 2016, leading all EMU receivers with 60 receptions for 868 yards and seven touchdowns.

[2][3] Bailey was signed by Tampa Bay Buccaneers as an undrafted free agent on April 30, 2018.

[8] In 2020, he opened the Surf & Soul Spot restaurant in the College Area/La Mesa which he co-owns with a childhood friend who is a chef.