McKenna joined Liverpool as a director when the club was founded in 1892 and was instrumental in putting the first team together, recruiting thirteen players out of Scotland. He then took charge of coaching the team, while W.E. Barclay handled administrative matters.
Although Liverpool were denied admission to the Football League for their first season, McKenna guided them to the title of the Lancashire League, leading to their election to the Football League's Second Division for the next season. Over the next three seasons, Liverpool were promoted, relegated, and promoted again before McKenna stepped down in 1896. But he remained active with the club, serving as chairman from 1906 to 1915.
Two years later, McKenna became president of the Football League and held that position until his death.
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