Bolton was born in Katanning, Western Australia and grew up in the southern Perth suburb of Forrestdale before spending his teenage years in Mandurah.

[9] Bolton made his AFL debut in round 9, 2017 in a match against Greater Western Sydney at Spotless Stadium and taking the place of the injured Dan Butler in the Richmond forward-line.

[19][20] Bolton returned to senior football in round 19 when he replaced the injured Jack Riewoldt, creating a forward-line without a recognised tall forward.

[30] Bolton was relatively ineffectual over the season's first two matches however, recording only three tackles and one goal in total and was subsequently dropped from Richmond's round 3 side.

[31] Despite his inability to impact at senior level, Bolton was immediately impressive in his first reserves match of the season, kicking three goals in Richmond's VFL win over Port Melbourne.

[36][37] He would also earn the competition's Goal of the Year when he scored from the forward pocket after repeatedly shrugging tackles during a match against the Essendon reserves in early July.

[39] It would last just one match however, with Bolton immediately dropped back to VFL level following a goalless nine disposal performance in the round 17 loss to Greater Western Sydney.

[49][50][51] He spent the off-season completing extensive personal fitness training, leading AFL Media and the Herald Sun to label Bolton likely to be one of Richmond's breakout players that season in a new role that would include playing time in the midfield and on the wing.

[61][62] While he recorded a then career-best 17 disposals in that match, Bolton saved his breakout performance for the following week, where he kicked four goals and was among Richmond's best players in a five-goal win over Fremantle.

[14][67][68] He was immediately prolific at that level, playing as an inside midfielder and turning in two consecutive best afield performances in which he held averages of eight tackles, 30 disposals, nine clearances and a goal.

[69][70] Bolton was recalled to AFL level following those two matches and the club's mid-season bye, kicking one goal in a round 15 win over St Kilda.

[71][72] In round 16, he seized an opportunity to play as an inside midfielder for the first time at AFL level, recording 26 disposal, nine marks and two goals as one of his side's best players in a 92-point demolition of Gold Coast.

[76] Bolton kicked a goal and set a new career-best with 29 disposals while repeating his role as an inside midfielder in round 17's win over Greater Western Sydney.

[89][90][91] In the week that followed, Bolton signed a new two-year contract extension with Richmond, reportedly rejecting outside interest from home town side West Coast.

[102][103] He finished what The Age and the Australian Associated Press labelled a "breakout" season by winning an AFL premiership, receiving five Brownlow Medal votes (fifth most among Richmond players) and placing 18th in the club's best and fairest count.

[104][105][106][107] Bolton received Richmond life membership in 2019/20 off-season for his contribution to the club's 2019 premiership win, but also underwent minor shoulder surgery that saw him on a non-contact pre-season training program through mid-February 2020.

[108][109][110][111] He resumed his place in the club's best 22 in two pre-season matches against Collingwood and Greater Western Sydney in March before kicking an equal team-high three goals in a round 1 win over Carlton.

[112][113] He also recorded 13 disposals in that match, which was played without a crowd in attendance due to public health prohibitions on large gatherings imposed as a result of the rapid progression of the coronavirus pandemic into Australia.

[121][14][122] With the news that the club would soon be relocated to the Gold Coast in response to a virus outbreak in Melbourne, and with the knowledge that senior midfielder Shane Edwards would not travel with his teammates, the club opted to send Bolton to the reserves level during the weekend of round 5 to play as an inside midfielder in preparation to play the role at senior level.

[133][134] In round 13, Bolton was best on ground in Richmond's Dreamtime in Darwin win over Essendon while the team wore an Indigenous artwork guernsey he had designed with the help of his family.

[145][146] He notched 17 disposals in the first up qualifying final loss to the Brisbane Lions, before kicking a match-high three goals in a semi-final win over St Kilda which led to AFL Media labelling him as "on the verge of stardom".