Right now the Winnipeg pick is 27th. To move up we need the following to happen:
1) Edmonton to beat Vancouver (I think a good possibility)
2) Colorado to beat Dallas (I think that's about 50/50, two pretty equal teams). If Colorado plays Vegas then it doesn't matter who wins
3) The winner of Boston-Toronto to beat Florida (very unlikely in my opinion).
Worst case scenario is 27, best case is 24, most likely 25 or 26.