A popular figure within football circles, Bailey coached Melbourne in 83 matches from 2008-2011 and played 53 games for Essendon between 1986 and 1992.
He was self-deprecating when talking about his playing career but he was a good junior player at North Ringwood before being a solid utility, both physically and in a footballing sense, with the Bombers.
His senior coach Kevin Sheedy said on Tuesday that Bailey was a lot of fun as a young man and an intelligent player.
As a coach, Bailey was renowned for his sense of humour and care for his players.
Dean Bailey dies at 47
"When you think back to his humour, [it was] very dry. [He was] a very good thinker about football and life in general," Sheedy said.
Although Bailey was suspended in February last year for acting in a manner prejudicial to the AFL's interests over his role in the 'tanking' affair at Melbourne in 2009, he retained the respect of most of those who worked alongside him in the game.
Many wondered whether the 16-week penalty handed down in 2013 was fair but Bailey accepted the decision and never complained publicly.
Adelaide, the latest club to benefit from his nature and football brain, stuck by him and welcomed him back to the fold as soon as his suspension ended.
Bailey began his coaching career at Mt Gravatt in Queensland after playing football for Glenelg from 1993-1996.
He became a development coach at Essendon in 1999 and was part of the group that took the Bombers to the 2000 flag.
He then became Port Adelaide's assistant coach from 2002-2007.
Wherever he went as an assistant success followed and he was renowned as a clear thinker with the capacity to lighten the mood when the situation demanded it.
He also possessed the hard edge that all coaches have, but did not reveal that side to many. Bailey had perspective.
At the end of 2007, he chased and won the vacant Melbourne job after impressing the selection panel with his personality and football smarts.
After starting the interview process as a long shot, Bailey beat several former coaches to land the gig.
He told an AFL coaches' conference in 2010 it was amazing where life could take you if you picked up the phone and pushed your case.
Bailey embarked on a rebuild as the Demons brought in a number of high draft picks, selected a new coaching panel and set off on an against-the-odds plan to develop a team that could contend for the flag.
He was beginning from a low base, with the Demons winning just one game in his first 13 as coach and ending his first season at the bottom of the ladder with three wins.
By the end of his third season however, the Demons had won eight games and appeared to be making progress under his attacking, run-and-gun game-plan.
They beat the Sydney Swans by 73 points at the MCG in round 17, 2010, and were hailed by some as football's next power.
However internal troubles were beginning to bedevil Melbourne as it entered 2011.
The players loved Bailey and worked hard for him, but the administration appeared to be less confident he was the right man for the job.
The Demons sat in the eight after round 14, 2011, when they beat Richmond by 27 points in front of 61,900 at the MCG, but there was disunity within.
Eventually the machinations became too great and when the team lost to Geelong by 186 points at Simonds Stadium – the second biggest defeat in the game's history – Bailey's days as coach were limited.
"I feel embarrassed," Bailey said after the loss.
He did not criticise the players and looked directly at his skipper Brad Green, who was standing nearby, when he told reporters he would always stand by his players.
"The biggest challenge will be that they stay united and they have just got to work their way through [this]. There is no point pointing fingers at all," Bailey said.
He was sacked as coach the next evening.
Bailey said he was a realist and accepted the decision with good grace.
In his final media conference with Melbourne he said he had no hesitation ensuring the club was well placed for draft picks in his first two years, and at the time the AFL did not see need for more than a cursory investigation of his comments.
But midway through 2011, with Bailey back as assistant coach at Adelaide, the AFL launched a full-scale review when former Demon Brock McLean – now with Carlton – suggested on Fox Footy's Talking Footy program that Melbourne had tanked in 2009, an inquiry that saw Bailey suspended.
Now Bailey has died too young, the rich mosaic of a life involved in football filled with more footballing ups and downs than most.
The AFL community is in mourning as thoughts turn to his family and friends.
"When you think back to his humour, [it was] very dry. [He was] a very good thinker about football and life in general," Sheedy said.
Although Bailey was suspended in February last year for acting in a manner prejudicial to the AFL's interests over his role in the 'tanking' affair at Melbourne in 2009, he retained the respect of most of those who worked alongside him in the game.
Many wondered whether the 16-week penalty handed down in 2013 was fair but Bailey accepted the decision and never complained publicly.
Adelaide, the latest club to benefit from his nature and football brain, stuck by him and welcomed him back to the fold as soon as his suspension ended.
Bailey began his coaching career at Mt Gravatt in Queensland after playing football for Glenelg from 1993-1996.
He became a development coach at Essendon in 1999 and was part of the group that took the Bombers to the 2000 flag.
He then became Port Adelaide's assistant coach from 2002-2007.
Wherever he went as an assistant success followed and he was renowned as a clear thinker with the capacity to lighten the mood when the situation demanded it.
He also possessed the hard edge that all coaches have, but did not reveal that side to many. Bailey had perspective.
At the end of 2007, he chased and won the vacant Melbourne job after impressing the selection panel with his personality and football smarts.
After starting the interview process as a long shot, Bailey beat several former coaches to land the gig.
He told an AFL coaches' conference in 2010 it was amazing where life could take you if you picked up the phone and pushed your case.
Bailey embarked on a rebuild as the Demons brought in a number of high draft picks, selected a new coaching panel and set off on an against-the-odds plan to develop a team that could contend for the flag.
He was beginning from a low base, with the Demons winning just one game in his first 13 as coach and ending his first season at the bottom of the ladder with three wins.
By the end of his third season however, the Demons had won eight games and appeared to be making progress under his attacking, run-and-gun game-plan.
They beat the Sydney Swans by 73 points at the MCG in round 17, 2010, and were hailed by some as football's next power.
However internal troubles were beginning to bedevil Melbourne as it entered 2011.
The players loved Bailey and worked hard for him, but the administration appeared to be less confident he was the right man for the job.
The Demons sat in the eight after round 14, 2011, when they beat Richmond by 27 points in front of 61,900 at the MCG, but there was disunity within.
Eventually the machinations became too great and when the team lost to Geelong by 186 points at Simonds Stadium – the second biggest defeat in the game's history – Bailey's days as coach were limited.
"I feel embarrassed," Bailey said after the loss.
He did not criticise the players and looked directly at his skipper Brad Green, who was standing nearby, when he told reporters he would always stand by his players.
"The biggest challenge will be that they stay united and they have just got to work their way through [this]. There is no point pointing fingers at all," Bailey said.
He was sacked as coach the next evening.
Bailey said he was a realist and accepted the decision with good grace.
In his final media conference with Melbourne he said he had no hesitation ensuring the club was well placed for draft picks in his first two years, and at the time the AFL did not see need for more than a cursory investigation of his comments.
But midway through 2011, with Bailey back as assistant coach at Adelaide, the AFL launched a full-scale review when former Demon Brock McLean – now with Carlton – suggested on Fox Footy's Talking Footy program that Melbourne had tanked in 2009, an inquiry that saw Bailey suspended.
Now Bailey has died too young, the rich mosaic of a life involved in football filled with more footballing ups and downs than most.
The AFL community is in mourning as thoughts turn to his family and friends.
