Bolton played his first senior game for Sydney against Carlton in round 12 of the 1999 season and received a Rising Star Award nomination the following year.

On Saturday, 9 April 2011, Bolton laid an AFL-record 19 tackles in a match, playing an integral role in victory over the West Coast Eagles.

In December 2013, Bolton was a crew member aboard racing supermaxi yacht Perpetual Loyal in the 2013 Sydney to Hobart Yacht Race, with other celebrity crew members, Karl Stefanovic, Larry Emdur, Tom Slingsby, Phil Waugh and Guillaume Brahimi.

He appeared as a contestant on the fifteenth season of Dancing with the Stars paired with professional dancer Dianne Buswell.

[citation needed] His wife, Lynette Bolton, starred in WAG Nation, a reality show that documented the lives of five wives and girlfriends of Australian sportsmen.