Bailey played 53 games as a centreman for Essendon before moving to the SANFL to join Glenelg. His most famous VFL appearance had been an incident where he as knocked out by Dermott Brereton in 1992 and spent the night in hospital with a severe concussion.
After three seasons in the SANFL he moved to Queensland and coached Mt. Gravatt for six years. Returning to Essendon, Bailey became a development coach with the Bombers before joining Port Adelaide as an assistant where he won a Premiership in 2004.
He remained at Port until being appointed to the Melbourne job in 2007. He had been on standby to coach a game for the Power in his last year when Mark Williams was in doubt with illness. After applying for the Melbourne job through an ad in the paper Bailey beat a star-studded field including former AFL coaches Kevin Sheedy and Chris Connolly, Demon caretaker Mark Riley and multiple VFL premiership winner Sandringham coach Mark Williams to take the job.
Bailey suffered an unkind welcome to his senior coaching career when his first match ended in a 100 point loss. The second wasn't much better and he narrowly avoided an extremely exclusive club of coaches who have lost both their first two matches by more than a hundred points. Pitted against the reigning premiers Geelong at Kardinia Park in round 3 Bailey's side produced a much better performance, kicking the first three goals of the match before succumbing to the much classier Cats.
The Demons won just three matches in Bailey's first season, the first a blockbusting comeback from a 51 point deficit against Fremantle in round 7. Finishing a game and percentage last, Melbourne 'earned' the right to pick first in the 2008 Draft and selected Jack Watts.
Bailey's side improved in 2009 but won just one more match than they had the year before. The team became embroiled in controversy late in the season when it became clear that the side might be good enough to win more than four games for the year and 'avoid' recieving a priority pick in the National Draft. The side ended up winning exactly four matches for the season, one loss in round 18 coming after the siren when Richmond's Jordan McMahon goalled. Bailey was once again thrown into the media spotlight after playing defender Matthew Warnock up front, and forward Brad Miller in the ruck. Bailey got his biggest ever victory the next week against Fremantle at the MCG.
Despite his statistically poor record (Bailey became the first coach ever to win two wooden spoons for the Demons) he earned a contract extension through the 2011 season. It was a controversial decision and the issue came to a head in late February 2010 as both Age and Herald Sun chief footballer writers generated opinion pieces on the issue.
When the Demons put in a listless performance in the round 1 clash against Hawthorn media commentators once again questioned the decision to grant him an extension. The next week the side went seconds from a shock victory against premiership contenders Collingwood, and then embarked on a three match winning streak including a slashing win against Brisbane where Bailey's brand of daring corridor football finally started to pay dividends. With three matches the Demons were still in contention for a finals position but lost all three matches.
Entering the last year of his contract under constant speculation about not only his own chances of earning an extension but also the backdrop of suggestions top draft pick Tom Scully would defect to Greater Western Sydney his side opened the year with a surprise Round One draw against Sydney but from then went on a rollercoaster ride which saw them only beat interstate teams as well as both Essendon and Richmond at the MCG, and Port Adelaide in Darwin in what would ultimately be his last victory as coach.
At the end of a week where it was suggested he would win an extension of at least one year his side went to Kardinia Park and suffered the second greatest loss in VFL/AFL history. After a crisis meeting the next day he became the third consecutive Melbourne coach to be removed in the middle of a season.
In September 2011 Bailey was named as Adelaide Strategy and Innovation coach, and remained with the club despite being suspended for the first four months of the 2013 season for his part in Melbourne's controversial 2009 campaign where he was accused of improper conduct surrounding games played late in the season.
Bailey was diagnosed with lung cancer late in 2013 and passed away from the illness a few months later.
Age - 15/11/2008