If Jake signs a deal like that (Guentzel resigns 8.5x5), then the Penguins would just keep him. Jake is signing for 8 years and he is signing for 10+ a year.

While I’m fine with the return, there is a very very slim chance that Guentzel is traded to New York. Also, I can’t see them moving Kreider. Also, Guentzel can do far better than 8.5 x 5 years. I can’t see him signing that contract, especially in the tax hell that is New York.

Kreider doesn’t waive

If Guentzel gets traded it's likely not a sign and trade, which means it won't be close to this return.

I'm also of the opinion that Rangers management wouldn't think the difference between Kreider and Guentzel would be multiple first round picks

Yeah Kreider isn't waiving for the oldest team in the NHL, And Guentzel is probably falling more in the 6x$9.5m range.

Guentzel isn't getting traded to the Rangers.

Kreider's not waiving and this does way more harm than good for the Rangers. I'm not even sure if Guentzel's an upgrade over Kreider with how much he's played with Crosby and there's no guaruntee he'll resign.

Think about if this does actually happen and Guentzel doesn't resign: We now have a huge hole at 1LW and are now without one of our most promising prospects and our 1st. That would go down as one of the worst trades of all time.

6 X 9.5 I'd happily take. Hell, I'd even take 6 X 10 maybe even 10.5. But if he wants 8 X 9.5 or 8 X 10 that's where I see the problem. Because it's obvious at some point in the next 3 to 4 years we're going to trade him. The return on him would be astronomically better if we're trading a 33 or 34 year old Guentzel with 2 or 3 years left on his deal making let's say 10 million than if we're trading a 33 or 34 year old Guentzel with 4 to 5 years left on his deal. Even assuming we'll be happy to retain a good chunk at that point in time, that's still a massive risk for a contender to take with that much term remaining on an older player. 10 will be the new 8 with the cap increases so I have no problem with 10 but we can't give Guentzel any more than 6 years imho....

Trying to fill one hole by acquiring Guentzel, while creating another equally sized hole in the process by moving Kreider, is counterproductive.

I'd take this return for Jake, but I doubt Kreider waives

Kreider..... let me get this right, you think the rangers will throw in Kreider, a guy who is a 35+ goal pace himself the last 3 years including this one.

The rangers tell you go to something yourself and hang up.