Winners and Losers of Connor McDavid's $25 Million Extension With the Oilers

Just one day before the start of the 2025-26 NHL season, Connor McDavid and the Oilers have agreed to a two-year, $25 million contract extension that will keep him in Edmonton through the 2027-28 season.

The $12.5 million average annual value is the same average annual value he's had since he inked his eight-year, $100 million contract ahead of the 2018-19 season. Some predicted a record-breaking deal with the cap rising, and with Kirill Kaprizov signing an eight-year deal with a $17 million AAV last week. Instead, McDavid opted to sign a bridge deal that will allow the Oilers more flexibility as the 28-year-old superstar seeks his first career Stanley Cup.

Does a bridge deal from the best player in the world set the scene for an interesting market going forward? Will the Oilers use the loose change wisely? Here are the immediate winners and losers of McDavid's $25 million extension with the Oilers.

Winners: The Edmonton Oilers

Andy Devlin/NHLI via Getty Images

The Oilers obviously wanted to lock down McDavid for as long as possible. But anytime you can sign the best player in the world to a $12.5 million AAV, you're winning for as long as that contract stands -- especially with the cap rising over the duration of the two-year contract.

Not only do the Oilers now avoid the constant questioning and distractions surrounding McDavid's contract this season, but they also know exactly where they stand. They've got two years and a considerable amount of cap space to go all in on a Cup, while McDavid's under his modest contract.

According to Puckpedia, the Oilers are projected to have $29.7 million in cap space next year now that McDavid's cost has been established. Leon Draisaitl, Zach Hyman, and Evan Bouchard are all locked down, so the Oilers will get to do some *cough cough* goalie shopping *cough cough* and more with more space.

Loser: The Oilers' Window

Mike Carlson/Getty Images

Connor McDavid and Leon Draisaitl

When it comes to a one-of-one player like McDavid, the Cup window is generally as long as the contract. Sure, McDavid could end up signing an extension with the Oilers after the next two years anyway, but for now, Edmonton has increased pressure to get it right and hoist the Cup.

It's especially tough after two years of making the Cup final and ending inches away from winning it all. These players have endured ultra-long playoff runs with nothing but exhaustion to show for it. McDavid's reasonable AAV could allow for the right players to come along and add some fresh legs to the lineup, like, dare I say, Brad Marchand did for the Panthers?

Winner: Stan Bowman

Andy Devlin/NHLI via Getty Images

McDavid could've walked away and moved on after Oilers general manager Stan Bowman failed to enhance the goaltending depth, but he's giving the new front office a few more tries to get it right.

Of course, we'll see what Bowman and Co. actually accomplish with McDavid's vote of confidence. But the fact that he signed before the last season of his current contract -- and the fact that he is giving the front office the cap space to make necessary moves -- gives the Oilers more than enough time to get it right, and that is a gift from McDavid.

McDavid can't trade for or acquire the right players himself, but he did everything else he possibly could to set the stage for success with this deal. Bowman wins the opportunity to get it right this time.

Winner: Stars Signing Extensions

Andy Devlin/NHLI via Getty Images

Connor McDavid and Kirill Kaprizov

Take your pick, NHL stars with upcoming contract negotiations: Would you like a record-breaking amount of money, or would you like a few years to help your team with cap space, then would you like a record-breaking amount of money?

Now that we've seen Kaprizov sign an eight-year, $17 million AAV extension and McDavid sign a two-year, $12.5 million AAV extension, we're seeing that now more than ever, stars will be able to choose their own adventure with their next contracts.

The market will settle down once teams settle into the current year's major cap ceiling growth, but the no-man's-land in between contracts signed before the salary cap jump and after is full of mystery and star player autonomy.

TBD: Connor McDavid

Matthew Pearce/Icon Sportswire via Getty Images

If anyone knows that you can do the right thing, be the best player, sacrifice for your team, and still lose -- it's Connor McDavid.

McDavid was the Conn Smythe winner on a losing Stanley Cup Finals team just two seasons ago and has now endured two straight seasons of failed trips to the Finals.

So, he's decided to believe in and stick with this Oilers group, and he's decided to give the team a chance to acquire lacking pieces with his contract. If they do him right, acquire the right pieces, and everything clicks, McDavid's first Cup is an instant classic piece of hockey lore.

Logically, we've seen plenty of Cup-winning teams take a few years of devastating Ls until it all clicked -- there's typically a building-up process that resembles what the Oilers have done.

Betting on the Oilers is as good a guess as any when it comes to McDavid's best chance to win a Cup for the next three years, especially since it was in his power to give them more wiggle room and he did.

At the same time, nothing's guaranteed in the Stanley Cup Playoffs. There's a chance we revisit this in three years and think, "Man, McDavid could've signed a $20 million AAV contract somewhere else, maybe even with a team that won any of the last two Cups."

Still, the contract is only two years long, and the cap is expected to keep rising in this timeframe. He'll get that record-breaking contract eventually, and he'll be able to either stay on board with -- or walk away from -- the Oilers gracefully, knowing he did everything he could to make it happen in Edmonton.

Now, Bowman, for the love of McJesus, start Googling the best active goalies in the NHL and pick up the phone this summer. It's largely in your hands to turn McDavid's "TBD" fate into a "winning fate," now.