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 AFL 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. As opposed to his emergency listing for the 2001 and 2002 Grand Finals for the Lions, Bolton was now a regular member of the team for Sydney, and as such played a part in the Grand Final victory over
West Coast, earning his first premiership medal, as well as finishing third in the club's Best and Fairest Award. Gradually establishing himself as one of the
AFL's standout defenders, Bolton was awarded a place in the
2006 All-Australian team on the half-back flank position, and again in the
2009 team at his preferred position of centre-half back. 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 SCG in Round 5, 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 AFL season.
Media career Following his playing career, Bolton commenced a media career as an Australian Rules Football commentator on
ABC Local Radio and also a guest commentator of the sport on the
Seven Network. ==Career achievements==