Obviously you don't realize it is no longer a 6 team league if you have doubts. Why even state something so ludicrous. Winning a cup now is like winning 5 cups in a 6 team league so winning 2 and there is your 10.
Not necessarily so. That "math" presumes all tams have an equal chance of winning each year which is only true in theory.
It was easier for the CANADIENS to stack a bunch of Stanley Cups in the 6-team NHL. Not so much for other teams. Although mathematically they had a much greater chance, in reality the Championship in 40's 50's & 60's was largely dominated by 2 teams in each decade, except for a couple of one-offs
(NYR 1940 & Chicago 1961) it was usually between Montreal and one other team. There was no free agency, very little path for a player to get out of a franchise that was spinning it's wheels.
In he last 20 years quite a few franchises were able to manage 3 Stanley cups in the space of 10 years, including both the Hawks & Penguins over just the past 10 years, so it is still quite possible for a fortunate player to retire with more Stanley Cup ring than Bobby Hull.
While it's highly unlikely anyone will ever get 10 again, 4 or 5 is quit possible given the way players can move and in some cases cherry pick their teams to get on contenders.