A native of
Portland, Oregon, Bailey attended
Douglas McKay High School in
Salem, where he won the 2007 Oregon State Championships 6A titles at 100 metres and 200 metres, and then went on to finish second and third over 200 metres at the Nike Outdoor Championships and USATF Junior Championships, respectively. After graduation, he began studying part-time at
Chemeketa Community College. He relocated to
Ina, Illinois in January 2009, to attend
Rend Lake College, known as one of the top junior college track and field programs in the United States. 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. His 100 m time made him the 13th fastest American sprinter in 2009. He turned pro in August 2009, signing with
Nike. In August 2010, Bailey ran a new personal best of 9.88 seconds in the
100 metres, finishing second only to
Nesta Carter (9.78 s) in
Rieti,
Italy. 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. At the
2012 United States Olympic Trials, he gained a place on the Olympic team by finishing third in the 100 m final with a time of 9.93 seconds. 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. He equaled that time again in the final for a fourth-place finish. He also competed in the men's 4x100m final and won a silver medal for team USA, equalling the Olympic record of 37.10 seconds behind team Jamaica. In 2016 Bailey tried his hand at
bobsledding, winning the National Push Championship preliminaries in August before winning the brakeman title at the Championships the following month. ==Personal bests==