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In 2011 he was named as coach of the Indigenous All Star team for their biennial game, this time against the Richmond Tigers. O'Loughlin also represented South Australia against Victoria in the State of Origin Slowdown charity match at the Adelaide Oval on 3 October 2011. Both teams were composed of retired players with the match supporting both the Little Heroes Foundation and the Reach Foundation youth charities started by former Melbourne Demons star player, the late Jim Stynes.

In 2010 O'Loughlin coached the Flying Boomerangs indigenous side during their Cape Town tour, leading the side to victory against the South Africa National Australian Rules Football Team. He was later named coach of the World 18 for the AFL National Under 16 Championships.

On 23 June 2009, O'Loughlin announced that at the end of the 2009 season he would retire. He played his 300th game in round 19 at the MCG against the Richmond Tigers.

Since leaving the AFL, O'Loughlin has continued a media profile. In September 2009 he launched the Goodes O'Loughlin Foundation (www.go-foundation.org), along with his cousin & co-Chairman Adam Goodes, focused on Education, Employment, and healthy Lifestyles. The Foundation's mission is to develop and empower the next generation of Indigenous role models in Australia.

O'Loughlin was awarded the 2009 AFL Players’ Association Madden for his on and off-field contributions to the game.

In 2006, O'Loughlin continued to be a key part of the Swans' line-up, including playing a decisive role in the qualifying and preliminary finals that put the Swans into the grand final for the second consecutive year. In the close qualifying Final against the West Coast Eagles at Subiaco Oval, O'Loughlin ran into an open goal, then carried on to the fence and roared into the faces of some rather stunned-looking Eagles' fans from a few inches away. The moment is captured in Jamie Cooper's painting the Game That Made Australia, commissioned by the AFL in 2008 to celebrate the 150th anniversary of the sport.

In the 2006 Grand Final, O'Loughlin played well, kicking 3.1 (19). He continued to play consistently well for Sydney through the balance of his career.

In 2005, he was selected alongside Sydney Swans teammate and uncle Adam Goodes in the Indigenous Team of the Century. O'Loughlin was chosen in the full-forward position. He described this honor as the highlight of his career, alongside the 2005 premiership.

O'Loughlin played the majority of his early football in a half-forward flanker role, where his combination of speed, strength and agility made him a difficult player for opposing teams to match up against. He was known by the nickname "Magic" throughout his career, in recognition of his capacity to play football so skillfully that it could sometimes seem he had "cast a spell" on his opponents. He was also known by the nickname, "Micky O". In the latter part of his career, he was primarily used as Sydney's full-forward. In 2000 and 2001, he was the club's leading goalkicker. He was club best and fairest in 1998 and runner-up in 2000. He was selected in the All Australian Team in 1997 and 2000. When State of Origin matches were still being played, he represented his state on several occasions, receiving the Fos Williams Medal for best South Australian player in 1998.

In 2000, it was alleged that O'Loughlin had participated in the rape of a woman in a park in Adelaide along with two other AFL players, Adam Heuskes and Peter Burgoyne. The woman claimed that while Heuskes and Burgoyne raped her, O'Loughlin masturbated close to her face. O'Loughlin was neither charged nor questioned by police but Burgoyne and Heuskes were both charged with rape. The case, however, did not go to court as the Director of Public Prosecutions, Paul Rofe, said there was "no reasonable prospect of conviction on any criminal charge" due to a lack of witnesses. Despite this, the three players made a $200,000 cash payment to the alleged victim. The incident came to public light when it was examined on the ABC investigative program Four Corners in 2004.

O'Loughlin, the only player remaining in the team from the 1996 loss, played strongly during the 2005 grand final, including a number of exceptional marks. However, and uncharacteristically, his kicking for goal during the game was inaccurate.

Selected in the third round of the 1994 National Draft, O'Loughlin played 12 senior games for the Swans in 1995 and earned a AFL Rising Star award nomination. The following year, he was a key player in the team that won the minor premiership and then lost to North Melbourne in the grand final. He was the games record holder for the Swans, passing John Rantall's VFL/AFL record in Round 14 of the 2007 season and Bill Windley's 102 year old overall club record in the Elimination Final of that year, until he was overtaken by his close friend Adam Goodes. He became the first Sydney Swans/South Melbourne player to break the 300 games milestone in Round 19, 2009.

Michael Kevin O'Loughlin (born 20 February 1977) is a former professional Australian rules footballer, who played his entire Australian Football League career with the Sydney Swans.