Edmonton Oilers, Draisaitl and McDavid have a delicious carrot and a nasty stick in contract negotiations

The contract for Leon Draisaitl is up next summer, the contract for Connor McDavid the summer after tha

Two questions dominate Edmonton hockey talk: Can the Edmonton Oilers retain them? And can they retain them on Stanley Cup-friendly contracts?

They key to these negotiations, as I see it, is that it not be oppositional, but instead both sides coming together to realize their deep and meaningful shared interest in winning the Stanley Cup, while treating both McDavid and Draisaitl fairly given their place on the team.

That is the win-win.

As per the NHL and NHL players’ association’s collective bargaining agreement, the two players will be free if they do not sign in Edmonton to go to any other NHL city at a maximum term of seven years and a maximum payment of 20 per cent of the salary cap.

I’ll suggest right now that if money is the top priority for either player, they will be able to get that 20 per cent bid from another team. It’s possible that Edmonton itself also would be able to give each player that 20 per cent contract on an eight-year term, though paying 40 per cent of the cap to any two players would likely doom any team’s Stanley Cup chances.

My point?

Edmonton has no obvious hammer in these contract negotiations. Draisaitl and McDavid are free to do what they will. After 11 seasons in Edmonton, the two players will be the full masters of their own destinies, the captains of their own ships.

It’s their negotiated right and I can see no reason why anyone should begrudge them that right, agreed?

The lure of Stanley Cup-friendly contracts

The conundrum for the Oilers is that if they pay Draisaitl and McDavid that full 20 per cent — as both players arguably merit at this point in their careers — the Oilers won’t be able to retain other top players in coming years, young players who need new deals like Evan Bouchard, Philip Broberg, Stuart Skinner, and Dylan Holloway, not to mention vets like Viktor Arvidsson, Jeff Skinner, and Brett Kulak, should those players be deemed as essential parts of Edmonton’s Stanley Cup aspirations

Even if the Oilers were to pay Draisaitl and McDavid 16 per cent of the cap, around $14.1 million per season based on the 2024-25 cap, the team would be hard pressed to compete for the Stanley Cup.

But what if Draisaitl and McDavid were to accept about $12.5 million per season, the same that McDavid makes now. That would be just 14.2 per cent per player of the 2024-25 cap, and a smaller percentage each year going forward, giving the Oilers more wiggle room to retain other good players.

That would be ideal for the team’s pursuit of the Stanley Cup. Those would certainly be Stanley Cup-friendly contracts.

But would it satisfy Draisaitl and McDavid? They would be missing out on about $36 million as compared to them grabbing the 20 per cent maximum on seven-year deals in some other NHL city.

For all that, I still think there’s an excellent chance that Draisaitl and McDavid will see it in their interest to sign Stanley Cup-friendly contracts in Edmonton, mainly because of one other key equation in the NHL also has to be factored in, namely that there are only two things in pro hockey: winning and misery.

The carrot of winning, the stick of misery
Both McDavid and Draisaitl now know well the misery of losing. They experienced the final years of the Decade of Darkness-plus. They had some playoff success in 2017 only to crash hard and fail to the make the playoffs the next two seasons. How miserable was that?

Their Oilers also crashed out of the 2020 and 2021 playoffs in their first rounds, another dreadful experience.

The Oil came come close, but not quite close enough these last three years, losing in the Conference, the Division and the Stanley Cup Final in succession. Painful and bitter losses all.

The Oilers came closest of all this past year, but they did so in part because McDavid and Draisaitl got paid just 25.2 per cent of the $83.5 million NHL salary cap last year (McDavid 15 per cent, Draisaitl 10.2 per cent), giving room for the Oilers to also pay for a solid player like Adam Henrique at the deadline.
If the players jump to 32 per cent of the cap, or even to 40 per cent of the cap, the ability of their team to win takes a beating, and that almost certainly equates to misery.

But if the two come in at 28 per cent, earning $12.5 million each, that is much more likely to calculate out to victory to winning, to the joy and glory of a Stanely Cup championship and both the boost in status and economic opportunity that comes with it

Of course, the big decision of the two players will come down to more than term, annual salary and whether the team might win or lose the Stanley Cup.

Do do the two players like playing here? Are they treated well here? Do they fit in here? Is the right city for them for the next part of their NHL careers? What do their partners want? What do their advisors and mentors think?

It’s a complex decision that has to weighed carefully and made based on multiple variables

But so far as I can tell the main leverage that the Oilers have in both signing the two players and having them happily agree to Stanley Cup-friendly contracts is the stick of misery and the carrot of winning.

In this way, the Oilers don’t have any hammer in negotiations, but the Oilers, McDavid and Draisaitl have one profound shared and mutual interest, to do all they can to win the Stanley Cup, whatever it takes.