The Edmonton Oilers have gone to two consecutive Stanley Cup Finals, but have not won the title. They have lost to the Florida Panthers in both years, and tensions are heating up in Alberta. Oilers captain Connor McDavid is entering the final year of his contract, which could lead to a media superstorm all year before the situation is resolved. Will it end in the largest contract in modern league history? Or will McDavid take a discount to bring a cup to Edmonton?
The NHL's salary cap is finally trending upward after a pandemic-induced pause. It will go from $95.5 million for 2025-26 to $104 million in 2026-27. That will leave the Oilers plenty of room to re-sign McDavid, even with Leon Draisaitl's $14 million deal kicking in this year. McDavid has already made $12.5 million against the cap for the past seven years.
The Oilers lived through a similar situation at the beginning of McDavid's contract, however. While he was winning MVPs and Draisaitl was dominating alongside him, the Oilers were missing the playoffs. The argument against Edmonton offering him a massive deal has everything to do with the cap and nothing to do with the player.
The Oilers have struggled to find a goalie during McDavid's prime, costing them valuable games in both Cup Finals. Stuart Skinner and Calvin Pickard are slated to return to the crease next year, which proved not to be good enough last June. Edmonton must save money to go find a goalie and get McDavd his title.
There are a lot of reasons why the Oilers should shy away from offering him a max extension. But if he and his agent decide they won't sign for anything less, there should be no hesitation in dropping the maximum contract in front of him. How will it end?
What will Connor McDavid sign for?

If McDavid remains with the Oilers, he will sign for eight years and $16 million per year, a $128 million total value. That would be the richest contract by AAV and total value in the history of the league. McDavid could sign for 20% of the salary cap, which would cap his salary at $20.8 million. They would be getting a significant discount by offering him the richest contract ever.
If McDavid were to leave the Oilers, a $20.8 million average annual value would be a near-guarantee. With teams jumping over each other to offer him the deal, negotiating up to the max would be quite easy. This is one of the best players in league history already, and there is no way to overpay him, even with the exorbitant salary.
The Oilers should prioritize McDavid over anything else this season. While there are things he may want to change about the organization, those can be done in the middle of the season. Despite not having great goaltending or having the proper depth in previous years, they have made it far in the playoffs because of McDavid and Draisaitl's brilliance.
Two other players who are entering the final year of their contracts could become the highest-paid players in the league. Kirill Kaprizov already turned down a $128 million deal to remain with the Minnesota Wild. There is optimism that he will stay in Minnesota, however. The Vegas Golden Knights already paid Mitch Marner, but still need to pay Jack Eichel. McDavid's 2015 draft classmate could break the bank, as well.
The Oilers could also offer McDavid a short-term deal that would put him back in free agency in three to four years. If he truly wants to set financial records, that would be the move, as the cap is expected to go up even more. What McDavid's priority is will become clear once he signs the deal. The official prediction is eight years, $128 million with the Oilers. But that is far from a guarantee.