Strachan was owner and president of the Montreal Wanderers from 1904 to 1909 during which the Wanderers won 3 of their 4 Stanley Cups in 1906, 1907 and 1908. In 1908–09, he also served as their head coach. He sold the club to P. J. Doran in 1909. The sale eventually triggered the formation of the National Hockey Association (NHA) when Doran moved the Wanderers to the Jubilee Rink. The Rink was smaller than the Wanderers' previous rink, the Montreal Arena, and the other Eastern Canada Hockey League members formed a new ice hockey league to remove the Wanderers. The Wanderers then formed their own league (the NHA) in partnership with Ambrose O'Brien. The ECHA's new league failed and some of the teams joined the NHA.
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