I'm a Habs fan. When Habs aren't in, for me it comes down to which players I like usually, more than actual teams. So based on that, here is the order in which I'd be rooting for teams to win the cup this year....
Pittsburgh (would love to see another Crosby smythe). Obviously - they might not even make it
Edmonton. McDavid will never touch 92 goals or 215 points in the regular season - but I could legitimately see him take a crack at Gretzky's single playoff run point record. Would love to see it. Drai isn't too far behind himself...
Toronto. This is all about Matthews - would love to see him break the goal record. Making fun of Leafs is hilarious when they fail, but I'm sure it would be extremely entertaining to follow if they won too...
Tampa. Love Kucherov, wouldn't mind seeing him land a smythe
NYI. I don't really like the team much, but I love Patrick Roy, would be a lot of fun to see him win a cup in year 1
Colorado. Another one for Makar/Mack
Vegas - Mostly because it'd be hilarious to see the meltdowns about cap circumvention again among fans.
I don't really care much about the rest. Outside of Boston. Who must not win, ever, because they suck.