Where do the 2025 Edmonton Oilers go from here?

The Edmonton Oilers have one big question to answer this summer and it has nothing to do with the team's seven pending free agents.

Well, almost nothing.

The big question is what happens with Connor McDavid, who will not be an unrestricted free agent until summer 2026, because he is eligible to sign an extension on July 1. As you might expect, everything the Oilers have to do this summer — which includes addressing six UFAs and one arbitration-eligible RFA — will be secondary to getting a big deal done with the best player in the world.

There is little to suggest that McDavid is unhappy in Edmonton, even given the results of the playoffs, where his team lost for the second straight year to the Florida Panthers. But the thing is, the AAV he commands will be the largest in league history, and probably by a fair margin. Currently, teammate Leon Draisaitl is locked in for the biggest cap hit ($14 million), and that's where the McDavid extension will start. One wonders how much McDavid, who has no want for endorsement opportunities on both sides of the border, will want to push his AAV beyond that, because even in an environment in which the salary cap is rising sharply, it's hard to pay two players — even the two very best on earth — a combined $30ish million against the upper limit. But the Oilers have no choice on this front, and frankly a $15-million AAV would be him doing Edmonton a favor.

So, all things are secondary to that and it isn't close. You move out whatever other contracts you possibly can, most obviously Darnell Nurse's, to make a McDavid extension happen. And here's where we acknowledge that maybe, just maybe, he wants to test the market or at least play a bit of hardball, because it's his right to do it and he could command a max deal in terms of both term and AAV. And to be clear, a max-dollars cap hit would be in the low 20s (20 percent of that season's projected $104-million salary cap), so it's no small difference between him doing the Oilers a kindness and testing the outer limits of what teams league-wide are willing to pay a player.

But this is the NHL and star players never move and they take less money than they could get elsewhere to stay with their current team, at least in the vast majority of cases. This is just everything that necessarily has to be discussed because it must be the Oilers' first order of business. Plus, the guy who runs the organization, CEO of Hockey Operations Jeff Jackson, used to be McDavid's agent, so this feels pretty aligned for the team, doesn't it?

Well, good. Because beyond that, they're already facing a cap squeeze. They have only a little less than $12 million to spend and, as mentioned, seven free agents to re-sign. First among that group is arb-eligible RFA Evan Bouchard, whose value was made clear once again in these playoffs. That value, you'd think, carries an AAV that starts with a "10." Which makes it hard for the Oilers to maneuver, straightaway. They don't really have many problem contracts on the books, apart from Nurse's ($9.25 million against the cap), Evander Kane's ($5.125 million), and Viktor Arvidsson's ($4 million). All those players have some sort of movement protection — Nurse and Arvidsson carry full no-moves, and Kane can veto a trade to 15 teams — and even with the cap rising, finding takers won't be easy. But something has to be done here, just because it's either lose those guys or struggle to re-sign Bouchard, unless he takes a bridge deal that walks him right up to UFA in summer 2028. Not sure why the player would do that, but it is technically an option.

Assuming Bouchard re-signs — and he almost certainly will — he would become one of seven defensemen signed for next season, and that likely means John Klingberg will have to look elsewhere for employment. He played pretty well for Edmonton coming off what a lot of people thought would be a career-ending injury, but he's also coming up on his 33rd birthday and has just 25 regular-season appearances over his last two seasons. Tough to gauge his value, but if he's coming back at anything more than like $1 million, which he very well could, that's difficult for the Oilers to swallow, mathematically. Both in terms of cap dollars and figuring out who goes where in the lineup.

Most of the other questions for the Oilers are up front, where Corey Perry, Jeff Skinner, Connor Brown, Kasperi Kapanen, and Trent Frederic are pending UFAs. They have 11 forwards signed for next season already, but at least one of those are guys will probably play more often in the AHL. Otherwise it's hard to see how any of these guys are coming back. Basically all of them could command more on the open market than the league-minimum contracts the Oilers will be able to offer them barring a radical change to their lineup which, again, is at least theoretically possible. Gotta think they'd like to have Perry back, even given his age, and would probably be amenable to re-signing Brown if the money is right. Frederic is a guy every Insider says they're re-signing, so I guess we'll take that as a given and just wait and see on term (max?) and AAV (it would have to be almost artificially low). Kapanen and Skinner? I would give them a hardy handshake and a "thank you for your service," personally.

All of the above is prelude to one last big question: How can the Oilers possibly try one more time with this goaltending situation?

Stuart Skinner and Calvin Pickard are both signed for next season and, while they do only cost $3.6 million combined, that feels like where the value proposition ends. Given the Oilers' demonstrated status as a team with legitimate Stanley Cup aspirations, do they dare run it back with these guys one more time? They can't, right? Well, given the cap constraints, the question might be whether you can find anyone you're more confident in for that price. Then again, if you think you can't keep turning to Skinner in the regular season or playoffs, maybe you just take the gamble on a relatively cheap replacement.

Again, if the Oilers find it's possible to trade Nurse, Kane, or Arvidsson, it's a whole different situation. Freeing up even $4 million (even if it means eating money on the Nurse deal, which runs through… 2030? Come on!) would go so, so far for this roster, just in terms of breathing room, but most of that money would have to go toward a solution in goal.

But everything everything everything is secondary to getting the McDavid deal done. Once you have that squared away, it all falls into place.