I would definitely pick Tampa Bay to Stamkos the Canuck get a Cup except I still haven't forgiven Tampa for this era:
So Washington it is, even though they are the underdogs.
Then of course there is the Winnipeg versus Vegas. Remember when the CFL expanded into the US and Baltimore won the Grey Cup? This won't be a repeat of that, so I'm picking Winnipeg versus Washington for the finals with Winnipeg getting the cup.