At 16 he was charged with assault, and at 18 he was sentenced to four-and-a-half years in prison.[2] He spent two years and seven months in a young offenders institution.[2] He became a father for the first time shortly after being released.[2]
Career
MacKinnon began his career with Dumbarton United, Dumbarton Harp, St. Thomas' and St. Patrick's Athletic, before joining Clydebank in May 2010.[3] Playing as a forward at Clydebank, he scored 31 goals in 69 appearances in all competitions.[4] He combined his Junior career with working on a building site.[2]
He turned professional with Hamilton Academical in July 2012,[2][5][6] making the unusual move up from the Junior level directly to the second tier of Scotland's professional setup at the age of 26.[2] After two appearances in cup competitions,[7] he made his debut in the Scottish Football League on 11 August 2012, appearing as an 80th-minute substitute.[8] He joined Ayr United on an emergency loan deal in September 2012.[9] Following his return to Hamilton, MacKinnon scored his team's equalising goal in a 1–1 draw with Falkirk after appearing as a substitute,[10] after which he stated that he wanted to start the next game.[11] MacKinnon later spoke about his hopes for a good run in the Scottish Cup,[12] and stated that the quarter-final against Falkirk on 2 March 2013 was the "biggest game" of his career.[13] A few days later, on 8 March 2013, MacKinnon signed a two-year extension to his contract.[14] In April 2013, MacKinnon publicly stated his support for new caretaker manager Alex Neil.[15] MacKinnon came fourth in the Hamilton 'Player of the Year Awards' for 2012–13, his first season in professional football;[16] he stated he would continue to fight for a place in the team.[17]
Once his second season began, MacKinnon spoke about how pleased he was with how the team were doing.[18] At the end of the season, he was part of the Accies team which won promotion to the Scottish Premiership, via a play-off win over Hibernian.[19]
In September 2014, MacKinnon was given a four-match ban after being sent off in a prior game.[20] In January 2016 he signed a new contract with the club until the summer of 2017,[21] and in December 2016 he signed a new contract until May 2019.[22]
Having begun to combine his Accies playing role with youth coaching duties at the club, in June 2018 the Under-17 team coached by MacKinnon (along with Dougie Imrie) became Scottish champions in the age group, qualifying for the UEFA Youth League.[23][24] In July 2018 he became Hamilton's captain.[25] As of March 2019 he was coaching the club's under-16s.[2]
MacKinnon was released by Hamilton in January 2020, and he was then signed by Partick Thistle.[26]