(Note: As stated, I have paid almost zero attention to the rest of the league this season. Hell, I barely kept up with the Sabres. So none of this information is meant to be taken as a prediction. These are just my gut feelings about who I think should win, in order to bring justice to the universe.)
1. Montreal Canadiens vs. Boston Bruins
I don't think I saw a single game the Sabres played against the Bruins this year, and yet I am totally sick of them. They somehow bring a type of boredom to the game that transcends things like actually watching them play, and the thought of cheering for them almost literally puts me to sleep. That being said, almost everyone around me is totally sold on the Canadiens, and I'm not sure why. Maybe their awesomeness doesn't transcend things like actually watching them play, I don't know. In any case, I can't think of any logical reason not to cheer for them, so Go Habs! I guess.
2. Pittsburgh Penguins vs. Ottawa Senators
I have a brain, ergo, Go Pens! Okay, really, the Senators make me sick. This ocean between us hasn't done anything to lessen that effect. Maybe I'm just a sore loser because the Sens played a primary role in derailing the first team I ever really, truly, and passionately cared about, but I'm stating here for the record that I will never, ever root for them. I just don't have it in me. That aside, a speedy exit from the playoffs would be just the picture-perfect end to a season that began with every Ottawa fan and half the MSM wanting to just cut the crap and stamp their names on the Cup already. As this year's Superbowl taught me, Schadenfreude attracts my rooting interest like nothing else.
3. Washington Capitals vs. Philadelphia Flyers
The Caps are a problematic team for me. I was perfectly content to cast them aside without a thought while they were still a (mostly) cute nuisance, perennially on the outside looking in on the post-season, but then this year they became impossible to ignore. Ovechkin had a stellar year, which everyone insisted on not shutting up about, to the point where they became increasingly obsessed with the possibility of the Caps making the playoffs, starting in about October. And then when they actually did manage to squeak into 3rd place (How crazy is it that that's possible? The Southeast is such a pit of despair), forget about it. I can't exactly pin down what it is that I don't like about the Caps (I don't exactly hate Ovechkin, though I resent everyone telling me how ecstatic I should be about him making his playoff debut), but one thing is for sure: I liked it a lot better when it was a given that they would suck their way out of the top eight. *Sigh* Luckily for them, they're playing the Flyers in the first round, so I see no choice but to say Go Caps. But I do so begrudgingly. (Sorry, Marty. You know I still love you.)
4. New Jersey Devils vs. New York Rangers
I would say stay tuned for the Western Conference edition of Gambler's Random Thoughts on the Playoff Match-Ups, but the truth is I can't be bothered to care. It's not like I ever paid attention to the Western Conference when we actually shared the same continent, anyway. I'll pick a team once we get closer to the Cup, I guess.