For the Wings, a lot honestly. Datsyuk and Zetterberg would have to stay healthy, our youth would have to take the next step and play with more consistency. Howard would have to be the goalie he was in the Anaheim and Chicago series two years ago. Our defense would have to play much better, ie Ericsson would have to step up, Dekeyser would have to take another step, and Smith would have to become a legit top 4 type of defenseman.
We would have a chance if we had a completely healthy goalie having a career year. otherwise I'd say we'd have to count on an even more unlikely scenario that saw an offensive explosion from several players...not just Vanek.
Realistically, it would take a ****ing ton for Calgary to even be a contender.
1. Giordano would need a repeat season.
2. Monahan, Baertschi, and Gaudreau (and possibly Bennett) would need to have monster seasons
3. Either Hiller or Ramo would need to have a Vezina worthy season.
4. They'd need to stay healthy.
For the Leafs, it would require an incredible amount of luck and a bold move or two.
-Bernier would have to show himself to be the real deal
-Rielly would need to have a breakout season similar to Doughty, Pietrangelo, Karlsson, etc from recent years
-Leafs would need to trade for an upgrade at C, very likely one well known for solid two-way play
-They would then still need to get lucky and wade through a weak Eastern conference. They would need a couple of Pittsburgh/Boston/etc to be upset by lesser teams to make their path to the Cup easier (similar to NYR and NJD from recent years), as opposed to getting three tough matchups back-to-back-to-back
-They'd need Bernier to steal them a series against a superior WC team