I don't think Hall or Leon are going anywhere, and adding McDavid as potential trade bait is blasphemy.
Chiarelli has a lot of work to do between now and the start of next year. Finding a defenseman who is better than anything the Oilers currently have, replacing Schultz with a better PP option, adding 2-3 top 9 wingers with size, aggression, and defensive reliability. I'd say we need to change out 5 players at minimum to become a playoff contender.
We are a playoff contender now. Give Nurse/Klefbom another year of development and have a little bit of luck injury wise in our top 6 and I think without adding a player we have a very good shot at the playoffs next year. We need to add one top 2 and one top 4 defender and we are going to start looking like a Stanley Cup contender.
We all have this perfect team paradigm that changes depending on who wins the Stanley Cup, but the truth is that every team has its warts and every team has its holes, its the teams that learn to play and overcome those(good coaching) that really become the top teams.
IE)
Power Winger(Nash) Big #1 Center(Toews) Offensive Dynamo(Kane)
Offensive Winger(Sharp) Two-Center(Kesler) Two-way Forward(Hossa)
Two-way winger w/ top 6 potential(Niederreiter) Two-way Center(Sobotka)Two-way Winger(Frolik)
Physical W(Martin) Faceoff Specialist(Gordon) Physical Pker(Hendricks)
#1 D(Keith) #2 D(Hamonic)
#3 D(Sekera) #4 D(Jones)
#5 D(Stuart) #6 D (Vatanen)
#1G(Rinne)
#2G(Darling)
And we want all of this under the cap, on perfect contracts to go along with perfect depth in the AHL, and hitting on at least one late round pick every year, never missing on our first and seconds.
What team has this? Noone. Some teams come close, like Chicago, like Tampa, but noone has it all. If we can somehow find a way to add a top 4 defenseman and one of Klefbom/Nurse become a 1/2 defender, we are pretty much as close as any other team in the league to that perfect paradigm. Does it mean we will win a Cup? Not necessarily.