A Great Britain and England international representative prop forward, he played the majority of his club career at Leeds Rhinos, having won six Super League championships and three World Club Challenges with the club. He was granted a testimonial in 2014.
Of Jamaican heritage, Bailey made his Super League début for Leeds in 2002 at age 18. In July 2003, Bailey was found guilty of brawling in the street in Leeds, and was sent to a young offenders' institution for 9 months.
In 2015 he moved to Hull KR. He was not fit enough to play former club Leeds Rhinos in the opening game of the season but went onto score on his debut the week after. In March it was announced Bailey had been released because of personal issues after only playing one game for the club.
A month later he joined the Castleford Tigers for the remainder of the season where he rejoined former coach Daryl Powell. He played 6 games and scored one try before being released at the end of the season.