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McKenna was recruited by the West Coast Eagles for the 1988 season with a pre-draft selection. He played for the Eagles from 1988 until 2000, notching up 267 games and booting 28 goals. He formed one of the most feared backlines in the AFL, along with John Worsfold, Ashley McIntosh, Glen Jakovich and Michael Brennan and was known for his cool demeanour and reliability. McKenna was also part of the club's 1992 and 1994 premiership sides.
He won the Club Champion Award twice, once in 1989 and the other in 1999, finishing in the top three another five times.
He was captain from 1998 until his retirement at the end of 2000. He kicked a memorable goal on the final kick of his career in Round 22 2000 which frenzied the crowd at Subiaco Oval.
McKenna boasts two unusual on-field distinctions from his career: In Round 20, 1994, he was the first player ever ordered from the ground under the blood rule, which had been introduced to the league that week. Then, in a match against St Kilda in Round 22, 1999, for the first time since Essendon's Jack Clarke in 1958, McKenna became the third captain in league history to call for a headcount; however, the teams were even.
McKenna joined Collingwood Football Club at the end of 2003 as an assistant coach under senior coach Michael Malthouse his former mentor. McKenna left the Collingwood Football Club at the end of the 2008 season.
Gold Coast senior coach (2011–2014)
In 2008, McKenna was appointed the inaugural senior coach of the newly founded Gold Coast Suns Football Club. He oversaw their TAC Cup and VFL campaigns prior to their entrance in the AFL. In the 2011 season, the Gold Coast Suns under McKenna in its inaugural season in the AFL league, finished in last place on the ladder with three wins and nineteen losses for the wooden spoon. In the 2012 season, the Gold Coast suns under McKenna finished in seventeenth position (second-last) on the ladder, yet again with three wins and nineteen losses. In the 2013 season, the Gold Coast Suns under McKenna improved on-field performance when they finished fourteenth on the ladder with eight wins and fourteen losses. In the 2014 season, Gold Coast Suns under McKenna finished in twelve place on the ladder with ten wins and twelve losses. But however after the Suns failed to make the finals in their first four years in the AFL senior competition league, McKenna was sacked as senior coach of the Gold Coast Suns on 1 October 2014, at the end of the 2014 season. McKenna was then replaced by Rodney Eade as Gold Coast Suns Football Club senior coach.
McKenna coached Gold Coast Suns Football Club to a total of 88 games with 24 wins and 64 losses to a winning percentage of 27 percent.
Essendon assistant coach (2015–2017)
On 9 November 2015, McKenna was appointed as an assistant coach in the position of line coach at Essendon under senior coach John Worsfold, who he previously played with as a former teammate at West Coast Eagles. McKenna left the Essendon Football Club at the end of the 2017 season.
South Australia 18.16 (124) defeated Western Australia 9.9 (63), at WACA, 16 June 1987
Victoria 16.20 (116) defeated Western Australia 13.14 (92), at Subiaco Oval, 22 July 1987
McKenna in June 2017