-
Greg Wyshynski
Connor McDavid responded to months of speculation by signing a contract extension with the Edmonton Oilers on Monday.
Notice how we didn’t say that he “ended” that speculation: McDavid’s contract, which carries an extremely team-friendly $12.5 million average annual value, is only for two years beyond this one, meaning the best hockey player in the world could still become the most coveted free agent in NHL history in summer 2028.
But if you’re the Oilers, you’re taking the glass-half-full approach. Or more to the point, a half-full (Stanley) Cup: Connor McDavid has at least three more chances to bring the first championship since 1990 to Edmonton.
As with any significant decision in the NHL, there are winners and there are losers.
Here’s the fallout from Connor McDavid’s new contract:
WINNER: Connor McDavid
Since it’s only a two-year extension, McDavid will have a slew of questions about why he chose that term and what it means for his ultimate future in Edmonton. But then after those questions are asked and answered, McDavid will focus on winning a Stanley Cup in Edmonton and a gold medal for Canada this season without being burdened with speculation. With this season and then two more, those questions can wait until at least September 2027.
This deal was done before the first puck was dropped on the NHL seasonand one has to assume Connor wanted it that way.
With McDavid’s contract situation settled, the entirety of the rumor mill will now focus on Crosby’s future with the Pittsburgh Penguins.
It’s a topic that Crosby is already sick of discussing but one that’ll grow in volume with each Penguins loss — and the pundits are predicting a lot of Penguins losses this season.
At least McDavid’s pending unrestricted free agency lured some of that spotlight away from Sid. Now, he’s the primary fuel source for this season’s rumor industry.
WINNER: Edmonton fans
When Oilers fans would say that McDavid wasn’t going anywhere, it sounded more aspirational than emphatic.
Maybe this season would be the last shot. Maybe he desired to play for one of the NHL’s glamour franchises, or one he felt had a longer contention window than Edmonton’s.
Visions of teary-eyed news conferences of the past filled their memories, like that time the other greatest player in franchise history ended up being The Great One in Los Angeles — heck, the Kings were even one of the teams that had the cap space ready for Connor next summer.
But he chose Edmonton. Not for the long term — at least not now — but he chose Edmonton. To continue living there. To continue playing there. Because he wanted to bring a championship there.
LOSERS: Everyone else
No McDavid rumor mill. No McDavid free agency frenzy. No McDavid arriving in New York or Dallas or Los Angeles or Tampa Bay or (gasp) Toronto to elevate those teams into immediate Stanley Cup favorite status. No hearing the faint sounds of the “Imperial March” as we tuned in to watch McDavid taking his talents from Edmonton to the highest bidder.
Yes, the smart money was always on him staying in Edmonton. It doesn’t mean the rest of us can’t be a little bummed that he left all that fun on the table — along with over $100 million in free agent riches.
WINNER: Stan Bowman
McDavid decided on Monday that he wanted to ink a two-year extension with the Oilers. That was after months of contemplation about whether — and if so, for how long — he wanted to commit to Edmonton. Part of that process was sitting down with Bowman to hear the GM’s plans for the Oilers moving forward. Ultimately, they got him to remain an Oiler for a few more runs at the Stanley Cup.
Now, one could say that the pitch enticed McDavid to remain with the Oilers for only two more seasons beyond this one, which might not say much for its effectiveness. And one could say that McDavid having essentially given Bowman money out of his pocket to spend should empower the player to have more say in organizational decisions. But, c’mon, no franchise player has that kind of pull within the organization.
On an unrelated topic: Congratulations to Oilers’ coach Kris Knoblauch, who coached McDavid in juniors, on his new contractgiven to him by Jeff Jackson, who is CEO of hockey operations and used to be McDavid’s agent.
LOSER: The Oilers’ runway
Now comes the hard part: Building a team around McDavid and fellow Oilers star Leon Draisaitl that can finally celebrate a Stanley Cup championship; or, failing that, one that convinces McDavid that the future in Edmonton is bright enough for him not to take his stuff and leave in 2028.
There’s frankly a better chance of the former happening than the latter.
The defending Western Conference champs bring back most of the same roster as last season, although the loss of Corey Perry might doom their Stanley Cup Final karma. After that, Bowman has some decent money coming off a rising cap next summer, including both goaltenders.
McDavid is essentially Uncle Jimmy in Season 4 of “The Bear,” slamming down a countdown clock until the restaurant is a success or goes bust. Bowman will spend the next three years frantically pawing at ingredients to find the right recipe.
WINNER: GM empowerment
Every NHL general manager has, at some point, tried to sell a player with an expiring contract on taking a little less to help the team in a salary-capped league. Most times, that player will absolutely refuse to be the victim of past contractual mistakes by management — maybe there’s a small hometown discount, but the stars want to be paid as such.
It used to be that Sidney Crosby was the model for contractual sacrifice, as he has had the same $8.7 million AAV since the 2008-09 season. Back then, it was 15.3% of the cap. On his latest extension, it’s 9.1% of the cap. As of now, McDavid will make 12.0% of the cap in 2026-27, although that could still decrease.
It’s team-friendly to the point that he’s not even the highest-paid player on the Oilers. Every GM in the league is going to harmonize when saying in unison: “Be like Connor.”
If the Oilers win during that two-year deal … well, now they have proof of concept, too.
LOSER: NHLPA
Any time a player decides to take less than market value, it’s not exactly a rising tide lifting others’ boats.
While the NHLPA was no doubt thrilled that Kirill Kaprizov got the Minnesota Wild to improve on what was already a record-breaking offer to settle on the highest value ($136 million) and AAV ($17 million on an eight-year term) in league history.
But the mind boggles at what McDavid could have landed as the most coveted free agent in hockey history, instead of maintaining his current cap hit for two more seasons.
WINNER: Leon Draisaitl
As I reported earlier this year, Draisaitl’s decision to sign an eight-year contract extension through 2033 did not mean that McDavid would commit long term to the Oilers, too.
As it stands, Draisaitl will have McDavid feeding him pucks for the next three seasons at a minimum. That’s three times better than just having him for the 2025-26 season, which was certainly a possibility as McDavid mulled his future as a pending UFA.
It’s not ideal, but it’s not catastrophic. And hey, he’s still the highest-paid player on the Oilers! Who saw that coming?
Of all the potential landing spots for McDavid, none would have knocked the hockey world off its axis like the Ontario native taking his talents to the Toronto Maple Leafs. A 1-2 punch of McDavid and Matthews might have convinced even the most cynical Leafs fans that the team could win its first Stanley Cup since 1967.
Alas, after losing Mitch Marner to the Golden Knights in the offseason, Matthews will have to wait until summer 2028 to potentially play with McDavid … when they’re both UFAs … and coincidentally share the same agent. Now that’s a fun summer.
WINNER: McDavid’s legacy in Edmonton
Assuming he plays the full term, McDavid will have given Edmonton 13 years of his life — after a bunch of draft lottery balls bounced the Oilers’ way in 2015 — in pursuit of the Stanley Cup.
He has lifted the team to two straight Cup Finals and three conference finals overall, to the point where he was just the second skater in NHL history to win playoff MVP in a losing effort. Two additional seasons might not sit well with some Edmonton fans, especially after Draisaitl committed to eight more seasons last September.
But the majority of fans likely see this as McDavid propping the contention window open by leaving a Scrooge McDuck money bin of free agent riches on the table, and giving the Oilers added cap flexibility. If he leaves in 2028, he won’t have abandoned Edmonton — it’ll be after giving that franchise his everything. If it ends without a Cup, it’ll be the Oilers’ legacy to have squandered it.
LOSER: The state income tax debate
The advantages for those teams that play in states without income tax have been restated and hotly debated ever since the Tampa Bay Lightning, Florida Panthers and Vegas Golden Knights started lifting the Stanley Cup. Players such as Brad Marchand have noted that a lack of state income tax has enabled teams to maintain roster consistency and attract talent.
But it didn’t lure McDavid on this contract. Which, as Panthers executive Roberto Luongo cheekily tweeted, doesn’t really stoke the fires of this burning issue:
No state tax strikes again! https://t.co/NCRxsSFBOy
– Strombone (@strombone1) October 6, 2025
He might still end up playing in Florida or Las Vegas or Dallas when this contract is up. But for now, he’s committed to playing in Alberta, where the income tax rate is 15%.
We’ll just have to wait for the Panthers to win a third straight Stanley Cup over the Oilers for that debate to reignite…
