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Odds of Leafs winning the Cup in the next 20 years

Got this from a friend yesterday:

"Recently made a bet with somebody... that the Leafs would win the Stanley cup in the next 20 years...  Interestingly, I am not confident."

Should he be confident?  If every team was equally likely to win the Cup in any given year, then the odds of any team winning at least one cup over the course of 20 years is 48%.  But we know that the Leafs are a below-average team right now, so we need to discount them a bit over, say, the next three seasons.  So maybe we're looking at 45%...Or less if you assume the Leafs will continue printing money and mismanaging their team. 

My friend was right to not be all that confident...