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How is this even a question???

Now, in the future, or in the past? Because its Edmonton no matter what.

Right now it's the Oilers because they have McDavid. If the Leafs can get progression in Matthews, Marner, Nylander, then the gap certainly narrows. And the Leafs in few years make have better flexibility ( no Lucic, Sekera, RHN)
Starting in 2020, I guess we're going to have a run of about 8 Cup Finals. all Oiler/Leafs

Oilers may make a few of those years, Leafs won't. They are just starting their "Edmonton experience", wait until all your little guns want big contracts 2-3 years from now!!!

Paul: I don't think any fan or any team should worry about too many good players. If there isn't enough money....so what....if they are good, they can be traded. It's signing players to bad contract that is cap killer.
The big unknown for any team is how much money....and it depends on how good they are is players coming on ELC. And there is no reason why a team is forced to do a Draisaitl type contract to players starting their fourth year in the NHL. Leaf aren't forced to offer Marner and Nylander 7m each. In 2019, the Leafs might have just one bad contact....Marleau and it's just 6.25m
There are a ton of teams with worse contracts....projected. Krejci, , Backes maybe even Rask and Bergeron for the Bruins. Giroux and Vorachek, MacDonald, for the Flyers. Staal and Lundquist Rangers.