After graduation, he began studying part-time at Chemeketa Community College.

At Rend Lake, Bailey won the 55 metres dash at the National Junior College Indoor Championships and, during the outdoor season, won the 100 meters and finished second in the 200 meters at the National Junior College Track & Field Championships.

His time of 10.05 was a personal best and a national junior college record.

[5] He also ran 20.10 to lower his personal best in the 200 m while placing third in the Weltklasse meet in Zurich, Switzerland and also finish the season third in the IAAF Diamond League 200 standings.

[6] Bailey began his Olympic debut at the 2012 Summer Olympics in London, by winning his heat in Round 1 of the 100 metres in a time of 9.88 seconds, equaling his personal best at that time.