Bolton grew up in George Town in north east Tasmania and played his junior football for the Northern Bombers in the TFL. Bolton was only nineteen when he caught the attention of the football world as a highly skilled rover who won three premierships in the TFL whilst also winning the Darrel Baldock medal, awarded to the Best on Ground during a Grand Final and the Horrie Gorringe Medal as the Best and Fairest player of the season. Bolton also played VFL football with the Tasmanian Devils and before returning to North Hobart as captain-coach. It was after his playing career that Bolton focused his efforts on elite level coaching. Following his success at North Hobart, Bolton quickly become regarded as a top level coach holding a variety of Assistant or Head Coaching roles at a including a stint as interim coach at the Tasmanian Devils, and senior roles at Clarence Football Club and the Box Hill Hawks in the VFL. Working closely with Box Hill’s aligned club Hawthorn, Bolton was rewarded with an Assistant Coach position with the AFL program. Bolton’s knowledge and understanding of the game continued to grow and his success at the Hawks, including five wins filling in for Alastair Clarkson piqued the interest of Carlton and in August of 2015 Bolton was announced Senior Coach of the Blues. Bolton spent four years at Carlton, before returning to Hawthorn as the Director of Coaching ahead of the 2020 season.

Bolton was only nineteen when he caught the attention of the football world as the highly skilled rover who played and won three premierships in the TFL whilst also winning the Darrel Baldock medal, awarded to the best on ground during a final and the Horrie Gorringe Medal as the best and fairest player of the season. Once Bolton was head hunted to coach the Hawks VFL team he then coached the team to two finals appearances and was then promoted to assistant coach under Alastair Clarkson in Hawthorn’s AFL side. Bolton’s knowledge and understanding of the game continued to grow and when he was appointed Interim coach where he was the first person to win five consecutive games in their first five matches as head coach. It was this success that saw Bolton scouted for the head coaching role at Carlton in 2015 where he again had a stellar start, coaching the side to four consecutive wins for the first time since 2011. After his four seasons at Carlton Bolton then moved back to the Hawks where he became the Director of Coaching and remains to date.