He won the Norm Goss Memorial Medal as best on ground during Richmond's reserves side's premiership in 2019 before making his debut in a victorious AFL grand final the following week.

[1] Later in 2007, Pickett was involved in a brawl alongside family members in the northern suburb of Bassendean and was subsequently charged with committing grievous bodily harm.

He was convicted for both the grievously bodily harm and robbery charges and served a six month juvenile detention sentence at Rangeview Remand Centre in Murdoch.

He resumed football with Koongamia, but was unable to find work, instead being charged with more criminal offences including driving without a licence and burglary.

As a bail condition for failing to appear in court for the latter charge, Pickett resumed living with his parents, who had relocated east of Perth to the town of York.

[1] Picket moved homes more than a dozen times over the next year, still unable to find work, before becoming an ice user and dealer not long after his 18th birthday.

He and a group of friends conducted two major early-morning burglaries by smashing into local shopping centres with sledgehammers on back-to-back weekends.

[5][6][7] Pickett served the first portion of his sentence at Acacia Prison in Wooroloo, where he suffered from serious mental health episodes and attempted suicide on four occasions.

[1] After over four years in the AFL having overcoming his indiscretions, Pickett was again remanded by West-Australian authorities on 11 June 2023, a day after a game played against Fremantle in Perth.

[1] He immediately took up an offer to train with West Australian Football League (WAFL) club South Fremantle at the insistence of his elder brother Tommy, who had been a reserves player there in 2012.

He was signed to the club's list almost immediately and played his first reserves grade game in late June 2013, two weeks after his release, where he recorded 15 disposals and two goals.

[1] Within two months he was called up for a senior WAFL debut, kicking three goals and recording nine marks, 26 disposals and eight inside 50s in a late-August match against East Perth.

[1] In 2015, he was moved to the half back line and was rewarded with selection in the WAFL/Western Australia representative team and also finished third in South Fremantle's best and fairest award.

[22][25][26] As part of that interest, he was interviewed extensively by Gold Coast and was flown out to tour the club's facilities and meet head coach Stuart Dew in person.

[30] In May 2019 while rehabilitating the injury, Pickett met with Essendon and Richmond recruiters and underwent an AFL medical screening prior to the upcoming mid-season draft.

[32] Pickett underwent emergency surgery on the night of the injury, with Essendon telling his management they were no longer interested in drafting him mid-season.

[35] Pickett participated in aerobic conditioning work throughout the first three weeks of his injury rehabilitation, joining the club's rehab group under the guidance of injured captain Trent Cotchin.<[1] He began full contact training in the last week of July and made a reserves-grade debut for Richmond's VFL side in the first weekend of August, kicking one goal and recording 20 disposals.

[48][49] In what earned the club its first reserves premiership since 1997, Pickett recorded 19 disposals, nine tackles and a goal in a best-on-ground performance that saw him awarded the Norm Goss Memorial Medal.

In the week that followed, Pickett burst into AFL selection consideration as a potential replacement for injured midfielder Jack Graham, the leading goal kicker in the 2017 Grand Final.

[5][55] When he helped to his side to a 89-point victory in that Grand Final, Pickett also became the first player to win a premiership in his debut game since Francis Vine with Melbourne in 1926.

[56] He was among the best players on the ground in the win, finishing third in the Norm Smith Medal voting with four votes (two from Angela Pippos and one each from Bruce McAvaney and Matthew Lloyd) behind teammates Bachar Houli and unanimous winner Dustin Martin, after a performance which included 22 disposals and his debut AFL goal off a set shot with 12 minutes played in the third quarter.

[63][64][65] Pickett recorded 14 disposals and an equal match-high five tackles in the win, played under extraordinary conditions imposed on the league as a result of the rapid progression of the coronavirus pandemic into Australia.

[81][82] Pickett earned an AFL recall in place of injured midfielder Dion Prestia in round 6, before an injury to Josh Caddy the following week allowed Pickett to cement a place of the wing in late July and early August, including with back-to-back 14 disposal and one goal games against the Western Bulldogs and Brisbane Lions in rounds 9 and 10 respectively.