Of course theres never a guarantee, but like Ray Bourque, you just sign (get traded) where the odds are high. Worked for him.... And if McDavid is smart, he'll just sign a 2 year deal. If he doesnt win, try with the next best contender. If he needs to accept a smaller salary to make it work under the cap, thats nothing to him since its a short contract.Where exactly is McDavid going to go to assure he wins the cup? Colorado looked like the best team until they lost. Florida was the best team but didn't even make the playoffs this season. Nothing is guaranteed in hockey. Buffalo and Montreal surprised this season. He doesn't quite fit their timeline but would one of them look to add McDavid? What if they do and they don't win the cup with him? I'm skeptical the Leafs are a good destination for McDavid but it's not like there is any obvious landing spot that guarantees him a cup.

WOULD but the oilers would never let that happen.
