[2] His father Billy Swan was a highly decorated footballer in the VFA, winning the J. J. Liston Trophy twice and playing a competition record 302 games with Port Melbourne and Williamstown from 1976 to 1993.

Swan's performances at the Calder Cannons were ordinary and he was perceived by some recruiters to be a larrikin with questionable kicking accuracy and work ethic;[4] however, Collingwood showed an interest in him as a potential late maturer in the mould of his father.

[1] Swan managed just 30 games in his first four seasons in the system at Collingwood, and although he played some solid football in that time, he was not regarded as outstanding.

2007 was considered his breakout season as he placed fourth in the Copeland Trophy and was a surprise packet at the Brownlow, leading for most of the night before finishing sixth with 20 votes.

The 2008 Copeland Trophy winner had a strong year averaging twenty-five disposals, seven marks, three tackles and one goal a game.

Swan was selected in the 2009 All-Australian team, but controversially as a half forward flanker, rather than as a midfielder, which is his usual position.

[9] With Swan's contract at Collingwood due to expire at the end of 2011, there was much pre-season media speculation over a possible move to new AFL club Greater Western Sydney.

[10] This was put to rest during the lead-up week to the season's commencement when Collingwood announced that Swan had signed a new three-year deal, committing him to the club until the end of 2014.

He attained 40 disposals in round 2 against North Melbourne but sustained a quad injury close to the midway point of the season and his form deteriorated.

Collingwood decided to send Swan, with teammates Brent Macaffer, Darren Jolly and Nathan Brown, to a high-altitude training camp in Arizona in an attempt to help the players recover faster from their individual injuries.

Strong performances over the following two months saw Swan rise in the Brownlow Medal betting, to become one of the favourites behind Jobe Watson, Scott Thompson and Gary Ablett.

Swan was later found to have broken a pledge made by the playing group to abstain from drinking alcohol for the remainder of the season.

Swan finished third in the Brownlow Medal with 26 votes, losing by two to the winner Gary Ablett, and one to second-placed Joel Selwood.

After 2014, a year that Swan described as putrid,[18] He returned to career-best form in 2015, averaging twenty-nine disposals and one goal per game, as well as reaching the 250-game milestone.

[19] Although Collingwood missed the finals, Swan arguably proved to critics that at the age of 31 he is still able to play high-quality football at an elite level.

[20] In the round one clash against Sydney, Swan was badly injured after landing awkwardly on his foot, breaking three bones, including a Lisfranc.

[24] In 2003, Swan was arrested with two others following a brawl at Federation Square in which a security guard (Jesse James) was knocked unconscious,[26] and another man (Claudio Celano) was left with a permanent brain injury.

Coach Mick Malthouse gave him a second chance, believing that Swan did not deserve to have his career derailed because of one stupid decision.