I like how McIndoe does his rankings, which is a "best chance to win the cup", rather than a "best team in the league" opinion piece. It takes into account playoff matchups, injuries and guys who will ultimately return from injury, locker room drama... everything that might cause you to win or lose a playoff series. In other words, you're almost never going to see the Leafs in it, because in order to win the cup they have to go through the Bruins and Lightning. Even the Bruins are a tough sell for basically the same reason.
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