Oilers' window to win might close after 2018 (Trending Topics)

When Connor McDavid signs his biggest-deal-in-NHL history early next week, a lot of people will have a lot to say about what he “should have” done.

Should have taken fewer years so he can cash in again in his mid-20s. Should have taken less money so his team can be more competitive. Should have waited another year so he could wring another million dollars out of this team when he inevitably becomes the league’s first back-to-back MVP since Alex Ovechkin almost a decade ago.

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But we’re in uncharted territory with McDavid here. There’s no saying what he should or shouldn’t do because no player has ever been so singularly valuable to his club in the cap era. Not Alex Ovechkin, not Sidney Crosby, not any other big-contract guy. It’s not hard to conjecture where the Oilers sit today if they get Eichel and some other team gets McDavid thanks to a couple lottery-ball bounces. The league has never been as rich as it is today: McDavid is the first player to clear $10.5 million AAV — and in fact, blow past it by more than 25 percent — and given his unique circumstances, it’s a territory few will even come close to approaching.

The money is big, but McDavid is worth it, especially because he gave Edmonton a conciliatory few years at the back end of the contract. If he truly wanted to cash in, he’d have gotten to unrestricted free agency as soon as possible and become the first $20 million player in league history. And the thing is, he’d have probably been worth it.

There is basically no amount of money you could give McDavid that’s allowable within the confines of the CBA — in which no one player can exceed 20 percent of the total cap limit — and have it not be “worth it.” In fact, extremely worth it. If you don’t think he’s the best player on earth you have still have to concede that day is coming very, very soon, and the value he provides to the Oilers not just on the ice but in jersey sales, getting on national TV, value to advertisers, etc. probably even surpasses what Crosby does for the Penguins. And again, if not now, soon.

But here’s something else that will soon come to be: One year from now, maybe two, people are going to start saying about McDavid what they’ve started to say about Patrick Kane and Jonathan Toews. They used to say it about Ovechkin, too. “He makes too much money. Yes he’s great, but it’s holding the Oilers back and they might never win a Cup as long as he has that contract.” And the thing is, just like Ovechkin to this point and almost certainly like Toews and Kane for the balance of their deals, those people might be right.

The Oilers’ window to win may seem pretty much wide open. McDavid is young and only going to get better. But given the cap constraints he places on the team — every dollar he gets is one Peter Chiarelli cannot spend elsewhere — it’s more reasonable to say that things might get a little dicey starting the second this new contract kicks in. You can see why here:

This obviously assumes Leon Draisaitl takes $6.5 million AAV, which might be a little optimistic for the Oilers. Some reports have started to emerge that his representation wants to put the boots to the club for sending him down his rookie season and costing him a year of unrestricted free agency.

You can adjust that Draisaitl number up or down by however much you feel is reasonable and the overarching point remains the same: The Oilers are going to spend in the high-$50-low-$60-millions range for just 13 players the season McDavid’s big contract kicks in. The year after that, probably around $52 million for just nine. And that’s without a new contract for what they clearly consider to be a franchise goalie.

And how much do you think the cap goes up in those seasons? Maybe another $5-6 million? Can’t be much more than that given how things have moved the past few years, and it might be less given the NHLPA’s distaste for the ever-growing escrow payments.

What that means to the Oilers is clear enough: They’ve built their expensive core for the next few years. A strong netminder in Cam Talbot. A top-four defense of Oscar Klefbom, Andrej Sekera, Adam Larsson, and Kris Russell (yikes). A forward group toplined by McDavid and Draisaitl, Milan Lucic, maybe Ryan Nugent-Hopkins (if they don’t Hall-and-Eberle him), and probably Jesse Puljujarvi (who by the way also needs a new contract in 2019-20 and won’t be cheap if he works out). That’s your ride-or-die group. It probably costs like $60-plus million two years from now.

And the cap will maybe hit $80 million in that time. If all goes better than it has the past few years. When Crosby and Malkin signed their jumbo extensions several years ago, those deals came at a time when the cap was growing fairly quickly in comparison to what it is now. That extra breathing room allowed the Penguins to circle back to being competitive five years or so down the line. The cap ceiling’s growth used to be at least 7 percent on a regular basis. The last two seasons it hasn’t exceeded 3 percent. (The estimated 4 percent growth noted in Greg’s post on this subject yesterday is therefore wildly optimistic.)

So while you can look at McDavid’s percentage of the cap right now and say it’s roughly comparable to what Crosby, Malkin, or Ovechkin got when they cashed in — on longer-term deals than the CBA now allows — you have to also understand that percentage is going to shrink a lot more slowly.

Again, this is not McDavid’s fault. He should take as much money as he can possibly get. That’s true of every single player in the entire league. But the issue is that Chiarelli has not been judicious in the contracts he’s given out, and that’s the real failing here. If Edmonton doesn’t win a Cup within the next few years, Chiarelli’s inability to identify what certain players are actually worth will be the reason why.

Did Lucic leave money on the table to play with McDavid in a gorgeous new rink blah blah blah? Undoubtedly. Some sucker out there would have given him an extra million a season, no question. But that doesn’t make Lucic’s buyout-proof contract good. It makes it less bad than it could have been. Russell’s deal is just bad business all the way around. An over-30 defense-first defenseman whose primary skill is blocking shots isn’t where I’d be super-willing to invest $16 million over four years.

McDavid and Draisaitl? You gotta pay those guys. Some of the other guys on the books for the next two or three years not so much.

The thing is, there was no way you couldn’t have seen this coming. The day you draft McDavid, you have to start thinking, “Okay, what does his contract look like when his ELC expires?” and plan accordingly. Chiarelli either didn’t do that or isn’t good at it. McDavid will get you to 50 wins a season almost by himself for the next five years at least. But that Lucic contract already looks regrettable based on the season he just had, and he’s only going to get older, slower, less impactful.

(This is to say nothing of the negative value he provides a few years from now relative to 25-year-old Taylor Hall.)

Apart from Lucic and Russell, there’s no single contract where you say, “This is a totally unreasonable overpayment.” But half a million here, a million there; it adds up fast. And when you gotta give out the richest salary in the league, even to a player who deserves it, you quickly come to understand how badly Chiarelli’s hands are tied.

Even if the salary cap somehow hits $80 million in 2018-19, it’s tough to see how Chiarelli puts much NHL-quality depth behind these guys unless every draft pick and rookie free agent signing they’ve had in the past few years works out exactly how they need them to. Or maybe if they go bargain-hunting behind the promise of “you’ll get to meet Connor McDavid,” which is actually a draw for the club.

They’ll need six or seven forwards, a defenseman to slot in behind Darnell Nurse and Matt Benning (both of whom will also need new contracts), and a backup goalie (probably a fairly cheap Laurent Brossoit or Nick Ellis). Can you get those 10 players — and have them be effective for you — for about $18-19 million? I’m not so sure.

It’s tough to guess where that really leaves the Oilers, except maybe to say, “Not as well-off as you’d think.” But that’s not on McDavid.

It’s on Chiarelli, who got caught paying non-stars too much money. Again.

Ryan Lambert is a Puck Daddy columnist. His email is here and his Twitter is here.

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