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.

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.

At the beginning of the 2008 season, Bolton was named Swans' co-captain, alongside Brett Kirk and Leo Barry.

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.