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 and playing a total of 29 senior games. He wasn't able to gain a regular place in the very strong Brisbane team of the time. When Brisbane won the flag in 2001 and 2002, he was listed as an emergency and did not actually play in the Grand Final. At the end of the 2002 season, he decided to leave the club.
Bolton was selected by Sydney in the 2003 pre-season draft and has played in all except one senior game since. His first three years with Sydney have mirrored his time at Brisbane, with the Swans' making the preliminary finals in 2003, semi-finals in 2004 and the grand final in 2005, just as the Lions did in 1999, 2000 and 2001. The only difference was that Bolton was now a regular member of the team, and so played a part in the Grand Final victory over West Coast, earning his first premiership medal.
On February 13 2008, Bolton (or "Bolts" as he's known to supporters) was given the distinction of becoming the Swans' co-captain, alongside Brett Kirk and Leo Barry. In May 2008, Bolton represented the Dream Team in the Hall of Fame exhibition match at the MCG.
He is unrelated to Swans teammate Jude Bolton.