Drafted 18th overall by the Hawks in the 2005 AFL draft, the ruckman from West Perth made his AFL debut in round 18 of the 2006 season. However, he would miss the 2007 season after suffering a right knee ACL injury during training before the season started. Max returned to the Box Hill Hawksreserves team for a game in June 2008, only to rupture his right ACL again which required another knee reconstruction. Max postponed the surgery to concentrate on his study then when the timing was right went under the knife. In May 2009 Max resumed training and was expected to play at the Box Hill Hawks in the later part of the season. However he made his return in round 21, 2009 and had 23 hit outs in a win over Richmond. The following week against Essendon, Bailey suffered another ACL injury after he landed awkwardly and badly twisted his good left knee five minutes into the game and had to be helped from the ground. He sat on the bench in frustration and missed the 2010 season. Throughout his succession of knee injuries, the Hawthorn Football Club kept the faith, retaining him on the senior list despite his first five years at the club yielding just six senior appearances. Max Bailey returned in round 9 of 2011 in a win over Sydney. Looking finally free of the injury curse, Bailey made a total of 16 senior appearances in the side that year. By trading 2008 premiership ruck Brent Renouf to Port Adelaide at the end of the 2011 season, the club effectively endorsed Bailey and the other rucks on the list to carry the mantle in 2012 and beyond. This plan struck a snag during the 2012 pre-season, when Bailey aggravated a wrist injury, which was set to keep him on the sidelines for around 12 weeks. During the 2013 season Bailey managed to cement a spot in the Hawthorn side, after playing well in round 1 in the Hawks loss to Geelong. Bailey's football career ended in the pinnacle of sporting achievements, being a member of Hawthorn's 2013 Premiership side. Former captain Sam Mitchell referred to Bailey as "the greatest story of the 2013 premiership," in a speech at the club's best and fairest, where Bailey ended his AFL career, retiring after 43 games due continued problems with his right knee.
Coaching career
After retiring from the game Bailey was employed by Football Club as a skills coach for two years, 2014–2015. Bailey spent six months in Tanzania before he accepted a position at his old club. In 2019 he coached the affiliate club Box Hill Hawks.
