Bailey was born on 5 January 1980 in Port Kembla, New South Wales. Initially a junior soccer player, he started to play rugby league at a junior level for the Shellharbour Sharks at the age of twelve. His talent was quickly noticed and while still an adolescent was signed to a junior development deal with Australian Rugby League club the Illawarra Steelers. While attending Warilla High School, Bailey played for the Australian Schoolboys team in 1997. At the completion of the 1998 season the Illawarra club was forced to merge with the St. George Dragons and Bailey's contract was renewed with the newly merged entity, the St George Illawarra Dragons.
After playing a sole season of lower grade rugby league with the Dragons, Bailey had impressed the club's top tier coaches enough to earn a spot on the bench for the Dragons' 2000 NRL season opener against local rivals the Cronulla-Sutherland Sharks; a game they would eventually lose twenty-eight to twelve. The 20-year-old made another two consecutive appearances from the bench but after a twenty-four to zero thumping at the hands of the Canterbury Bulldogs he was dropped for their round four clash with the Northern Eagles.
Bailey remained in the lower grades at the Dragons before earning a recall to the first grade side against the Wests Tigers in round six and a week later was given his first starting berth by coach David Waite. After an impressive performance during the team's win against the Auckland Warriors during his first start Bailey remained a staple fixture in the starting line-up, playing in every remaining season fixture and cementing his starting position in the clubs line-up.
After an impressive first year, Bailey began the 2001 NRL season in a starting spot in the front row. He appeared in the Dragon's first four appearances of the season but tore a pectoral muscle during the team's loss to the Warriors, an injury which ruled him out for the rest of the season.
The beginning of the 2002 season saw Bailey recover fully from the injury that had prematurely ended his previous playing year and while he missed all of the clubs trials including the Charity Shield fixture against South Sydney he made his return to the team for their opening round clash against Cronulla-Sutherland and would go on to appear in a further twenty consecutive appearances putting in several man of the match performances and along the way earning himself a call up to the New South Wales State of Origin side. Bailey made his State of Origin debut for the New South Wales Blues in game I of the 2002 series. He featured in the run-on side in all three games of that drawn series. During the Dragons round twenty-one loss to the Newcastle Knights Bailey found himself being severely reprimanded for the first time in his short career after opposing forward Josh Perry had claimed Bailey had bitten him on the forearm before withdrawing the allegation moments later. The seriousness of the allegation and the media frenzy that followed however saw Bailey being called up to face the NRL Judiciary however he was later cleared of any wrongdoing.
Five weeks later when the Dragons again took on the Newcastle side the spotlight was again on Bailey for a disciplinary issue with Knights coach Michael Hagan claiming that a tackle from him had injured Newcastle captain Andrew Johns and ended his season, however he was not charged over the incident.
2003 started well for the Dragons with six victories from their first eight games. Bailey would receive his first call up for the Australian national side during the 2003 season where after some impressive performances he would play his first game during the 2003 Anzac test against the New Zealand national side. However Bailey injured his back during a fixture against the Penrith Panthers and was left with a severe lower back strain after being cleared of a suspected fractured vertebra. This injury became a somewhat re-occurring one and hampered his season keeping him out of several matches throughout the year. In 2003 he again made three appearances for the Blues – all as an impact player coming off the interchange bench. He was Man of the Match in game I of the 2003 State of Origin series. Further injury at the completion of the year ruled Bailey out of the Australian national side for their end of season Northern hemisphere tour after he required surgery to fix a damaged ear.
After missing the Australian tour and having his first full off-season of training under his belt since 2002 meant that Bailey would play in the Dragons trial matches that year including their 34 – 8 victory in Charity Shield against the Rabbitohs. However the actual season did not start as positively with Bailey being placed on report for a dangerous tackle in the season opener against the Canberra Raiders and then subsequently being charged and forced to miss the round two clash with the Warriors. Bailey returned from suspension a week later in the Dragons loss to the Melbourne Storm and then went on to play the next few rounds for the Dragons with several strong performances earning him an Australian call up. Bailey earned his second international cap when he was selected to play for Australia from the interchange benh in the 2004 ANZAC Test match against the Kiwis but not make another appearance for a few years. Though injury again hampered him during a regular season fixture against the Sea Eagles in round nine where Bailey re-injured his pectoral muscle as he had also done in 2001 which meant he was in for another lengthy stay on the sidelines being ruled out for the entire regular season. A torn pectoral muscle in 2004 saw his season disrupted and he took no part in Origin that year. He eventually made his return during the final series but not even his presence could help the Dragons from narrowly losing to the Penrith Panthers.
2005 looked a promising one for both the club and Bailey, who started the season without any injury or suspension clouds hanging over his head. A promising start to the season would continue for the club helped by lack of injuries to key players including 'Bull' Bailey who would go on to make a total of twenty-three appearances for the club guiding them to equal top position of the ladder after all regular season games sitting just behind Parramatta on points difference. On 23 June 2005; it was announced that the newly formed Gold Coast Titans club was chasing the signature of Bailey for its inaugural 2007 season. It was confirmed later that month that he had signed a three-year deal with the club beginning with the first Titans season and finishing in 2009. Bailey appeared in all three games of the 2005 State of Origin series. The 2005 finals series saw Bailey put in an impressive performance in a tough game against the Sharks but all would be in vain as the Dragons would eventually lose in the preliminary finals to eventual winners the Wests Tigers.
Bailey played for the Blues in games II and III in 2006 State of Origin series. Bailey played his last season for St George Illawarra in 2006.
Since joining with the Gold Coast club Bailey has been heralded as the rock on which the Titans forwards will rely on to start their debut season as possibly best they can and while the club would end up losing its first match by two points to his previous club the St George Illawarra Dragons they would start the season with a 3 and 2 win/loss record. Bailey was selected to play for the Australian national team from the interchange bench in the 2007 ANZAC Test match victory against New Zealand. Bailey played for the Blues in all three games of the 2007 State of Origin series off the interchange bench. By the end of the Origin series of 2007 he had made fourteen appearances, eight off the bench. At the end of the Titans' first season he was named co-winner of the club's inaugural Paul Broughton Medal for best and fairest player of the season with teammate Anthony Laffranchi. He scored the first try for the Titans at Skilled Park in the 2008 Opener. He was selected for Australia in the one-off test match against New Zealand on 8 May 2009. In May 2009, Bailey was named in the 17-man squad to represent New South Wales in the opening State of Origin match on 3 June 2009, in Melbourne.
After playing in the Titans' last few matches of the 2010 NRL season with a broken thumb, Bailey was awarded the Paul Broughton Medal for the club's player of the year again.
On 1 September 2014 Bailey announced his retirement from Rugby League. He was one of two of the Titans' foundation players alongside the departing Mark Minichiello who'd remained with the Titans since their inaugural year in 2007.