I think before you trade Guentzel, you have the following conversation:
Jake, you're a UFA. Do you want to continue your career here or not?
If not, we will trade you for assets.
If you do, we have two options:
1. Resign you early.
2. Trade you to a contender, you get the chance at the cup, we get the high level assets back, and we resign you in the off-season.
I don't think you can trade Guentzel without having a plan in place to replace him. And the plan can't be "sign Bertuzzi". It just can't be. As I suggested earlier, I wouldn't be shy about working a deal to take a middle 6 guy and a 1st for Jake, then resign Jake July 1st. In my post, I suggested Garland+1st for Jake+DOC
Next year:
Jake-Sid-Rust
Smith-Malkin-Rakell
XXXX-Eller-Garland
Neito-Accari-XXXX
Lots of interesting options there, especially with a tight cap. You can take back a $3mil winger and keep 50% of Jake. If we are out of the playoffs, I wouldn't hate trying to stick it to a local team that we wouldn't normally be dealing with like NYR, NYI, CAR, etc. NYR are never shy about spending. Wonder if you can snag Kakko+1st for Jake@50%. Or Goodrow+1st+ for Jake@50%.
Ottawa - Joseph+Pinto for Jake@50%+Smith
LA - Grundstorm+1st for Jake@50%
Just spitballin...