Good god man look at the long, long line of *very* good teams that don't win the Cup. That's bold. Think about a Sharks fan 5 years ago looking at their elite AF squad and the confidence they'd have felt in that prediction... and frankly the Leafs ain't exactly the 2009 Sharks. The way it is now if you're going into a season with a team you can confidently predict will be one of the top 3 in the league I think they will be around 20% to win the Cup. Las Vegas (not the team) can probably tell you more accurately, maybe it's around 30% but that feels too high.
This is all tied into my long held and quite realistic belief that it's doubtful my team will win the Cup in my lifetime (even if they weren't sub-par for the last half decade). Just statistically it's doubtful. Luckily I have Team Canada to fill the championship gap.
EDIT: also, important to note that my incredibly low expectations are still somehow not being met by this jackass team. What the fuck, I entered this fandom NEVER expecting to actually win and they manage to underwhelm. Listening to Hockey Central on the way home and vomiting at the panel of fucking experts talking about how great Maurice is and how he's close and he deserves another shot is bracing me for more of the same next season.