Karlsson has not been the same since signing that deal in SJ now way should anyone acquire that deal. $8M+ at 30 for the next 6 years does not seem like a good long term move

I love the bold idea and something that's clearly outside the box thinking!

But I think as is, San Jose won't have any interest in this deal. When's the last time someone retained for that long? Last time I can think of is the Kessel to Pittsburgh deal which was only 15% of his contract and $1.2M in real money. In a cash strapped and flat cap world, I can't see San Jose wanting to retain $3.25M per season and the returning package doesn't really help that. If they're looking for prospects, I'd think Cam York or Bobby Brink would have to start to be involved, and I think they'd want a young roster player as well. I'd say either Sanheim or Myers.. so for handedness and argument sake, I'd say a package likely starts with Brink and Myers. Sending Gostibehere helps with the cap, but I think Gostisbehere just needs a change of scenery and he'd do very well. Maybe you could entice San Jose with Nolan Patrick since Philadelphia has been shopping him hard instead of Brink. But already sending 2 roster players I wouldn't think a 3rd would be something Philly would want to do. I'd also argue that a 1st wouldn't be involved. Karlsson hasn't been his old MVP self and its a rough contract to take on, so I think most teams will steer clear of a 1st going the other way.


F - Bobby Brink
D - Phillippe Myers
D - Shayne Gostisbehere
2021 4th round pick (PHI)
2022 2nd round pick (PHI) - Conditional (becomes a 1st in 2022 if Karlsson wins the Norris trophy in 2021/2022 or Philadelphia wins the 2022 Stanley Cup)


D - Erik Karlsson (15% retained - $1.65M)
F - Noah Gregor
2022 5th round pick (BUF)


This would be something that might be closer for both teams to make IMO. I think Philadelphia would look for a depth forward at centre in the deal as well in case Frost doesn't pan out next season as a 3C so I added in Gregor for a fit.

Thanks for the thorough reply. Outside the box was exactly what I was going for. Just a fun thought experiment, trying to take account of what these GMs, and the pressures they are under, might make possible.

Regarding retention, I knew this would come up. One one hand, there simply is no comparable deal because no one has an $11.5 AAV but EK himself. You are right, Kessel was the appropriate length and 15% of the salary retained for 6 years is less than the 28.2% retained for 6 here. That said, those same Penguins have on their books retention for Nick Bjugstad at $2M AAV on just a $4.1M contract sold to Minnesota. That's 48.78% of the total. I could dig for hours and fail to find an exact match, but the point is there are transactions retaining greater percentages at shorter length. It is what it is, but I disagree that 28.6% is outside the realm of probability should EK be dealt.
(Edit: Consider as well that there are buyouts that have been more severe, and teams still took that on. For example, the Devils have Cory Schneider's buyout at 2mil AAV for 4 seasons. The Kings have $4M AAV from Phaneuf this season before it drops to 1 and change. Also, I beg of you to look at the NY Rangers buyout situation cumulatively; it's a lot of salary and they got nothing for it, unlike a trade and retain scenario).

Regarding the consideration going the other way, I want to stress that it is an open discussion whether Zamula or York is the better prospect. York has some more name recognition b/c of draft status, but Zamula's production in juniors was frankly insane and he has looked the part in Lehigh (AHL) while being asked to focus on his defensive game. Brink is a good one to bring up; I think he could be bargained into the deal, but not at less retention. That doesn't add up. Selling Myers or Patrick doesn't make much sense either, as the Flyers are trying to win now/soon and these guys are in the NHL right now, albeit while struggling. Neither of them are high in stock price right now, so younger prospects performing well should look more attractive to San Jose than some arguable busts. All that said, I have no idea what the exact right consideration is; I'm just a guy taking a stab at a blockbuster move that could happen, around these core components anyway.

I agree Philly could add a 3C if Frost doesn't pan out, but I expect he gets the chance before they bring someone in to fill the role. Maybe mid-season or at the deadline you see a 3C move if there is a void there and the rest of the team is clicking. (Edit: There is also the option of moving Giroux back to center, and shifting Hayes down to 3C, which frankly I am adamant about doing).

Thanks again for your feedback.