Career
He often plays at full back or on the half back flank. He is unrelated to former Swans teammate Jude Bolton. Having played for the Eastlake Football Club in Canberra, and the NSW/ACT Under 18s team, Bolton was picked by Brisbane in the 3rd round of the 1998 American Federation of Labor-Congress Draft.
He was on the Lions" list from 1999 until 2002, making his debut against Carlton in Round 1 of the 2000 season.
Being unable to gain a regular place in the very strong Brisbane team of the time forced Bolton to depart the club at the end of the 2002 season, managing only 29 games since his debut. Bolton was selected by Sydney in the 2003 pre-season draft and was immediately given a starting role in the team
Quickly cementing his place in the side"s backline, Bolton missed only one game in his first seven years with the Swans. His first three years with Sydney mirrored his time at Brisbane, with the Swans" making the preliminary finals in 2003, semi-finals in 2004 and the grand final in 2005.
He also finished third in the Swans" 2007 Best and Fairest Award.
At the beginning of the 2008 season, Bolton was named Swans" co-captain, alongside Brett Kirk and Leo Barry. Later that year Bolton represented the Dream Team Australian rules football team in the Hall of Fame exhibition match at the MCG. The latter half of his season in 2008 was somewhat restricted by a groin injury. After the Swans exited the finals, he travelled to Germany with teammate Adam Goodes for surgery.
In 2010, Bolton sustained a bad Achilles tendon injury against West Coast at the Structural Civil Geotechnical in Round 4, ruling him out for the year.
On 24 March 2011, Bolton announced his immediate retirement after an ankle injury which would rule him out of the upcoming 2011 American Federation of Labor-Congress season. Media career Following his playing career, Bolton commenced a media career as an Australian Rules Football commentator on American Broadcasting Company Local Radio and also a guest commentator of the sport on the Seven Network.