The first year the Stanley cup was given (as the unofficial trophy) to the NHL Champions was 1926, the year before the above advertisement was printed.
Second, The advertisement is for cigarettes. Fatima cigarettes, an American brand that was the best-selling cigarette from 1910 to 1920 and had been primarily marketed to well-to-do prosperous sorts as a cigarette of distinction.
However, Fatima cigarettes were well past their tipping point by 1927 and the manufacturer would discontinue advertising the brand completely during the great depression of the 1930's (though advertising would resume in the1940's and the cigarettes remained in production until 1980).
Being as how hockey as a professional sport was in it's infancy, and Fatima cigarettes were in a steep decline, why in the world were the two married up in an advertisement?
I'm going to assume that the above advertisement was an attempt by the manufacturer and whatever ad agency they had hired to reposition the cigarette brand as a unique niche item that would bring an aura of youth and vitality to the discriminating cigarette smoker.
Because that's what cigarette people do, try to make death-on-a-stick look appealing.
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