Following months of intense speculation, Connor McDavid officially signed a contract extension with the Edmonton Oilers on Monday. However, it`s crucial to note that this doesn`t “end” the speculation entirely: the contract, a remarkably team-friendly deal with an average annual value of $12.5 million, extends only for two additional years beyond the current season. This means the world`s best hockey player could still become the most sought-after free agent in NHL history in the summer of 2028.
Nevertheless, for the Oilers, the outlook is overwhelmingly positive. Or, more precisely, they see the glass as half-full, perhaps even a half-full Stanley Cup. Connor McDavid now has at least three more opportunities to bring Edmonton its first championship since 1990.
As with any significant decision in the NHL, this extension creates both winners and losers.
Here`s an analysis of the key players and entities impacted by Connor McDavid`s new contract:
WINNER: Connor McDavid
While this two-year extension will undoubtedly prompt numerous questions about his decision and what it implies for his long-term future in Edmonton, McDavid can now set those discussions aside. He can fully concentrate on his primary goals: winning a Stanley Cup for Edmonton and a gold medal for Canada this season, free from the burden of constant speculation. With the current season plus two more, any persistent questions about his future can comfortably wait until at least September 2027.
It`s clear this agreement was finalized before the start of the NHL season, suggesting McDavid preferred to have his contract situation resolved beforehand.
LOSER: Sidney Crosby
With McDavid`s contract status no longer a talking point, the entire focus of the NHL rumor mill will now shift squarely onto Sidney Crosby`s future with the Pittsburgh Penguins.
This is a topic Crosby is already weary of addressing, but its intensity will only amplify with each Penguins loss – and many pundits are predicting a challenging season for Pittsburgh.
At least McDavid`s impending unrestricted free agency previously diverted some of that intense scrutiny away from Sid. Now, Crosby has become the primary subject fueling the season`s gossip industry.
WINNER: Edmonton Fans
When Oilers fans asserted that McDavid wouldn`t be leaving, it often sounded more like hopeful thinking than a firm conviction.
There was always the lurking possibility that the current season might be their last chance, or that he yearned to play for one of the NHL`s more glamorous franchises, or one he believed offered a longer championship window than Edmonton.
Memories of past tearful press conferences, like when the franchise`s other greatest player, Wayne Gretzky, became “The Great One” in Los Angeles, undoubtedly lingered. The Kings, in fact, were among the teams that had the necessary cap space ready for Connor next summer.
But he chose Edmonton. Not necessarily for the long term – at least not yet – but he chose Edmonton. To continue living there. To continue playing there. Because he is committed to bringing a championship to the city.
LOSERS: Everyone Else
No more McDavid rumor mill. No McDavid free agency frenzy. No McDavid potentially arriving in New York, Dallas, Los Angeles, Tampa Bay, or (gasp) Toronto to instantly elevate those teams to Stanley Cup favorite status. No hearing the faint sounds of the `Imperial March` as we anticipated McDavid taking his extraordinary talents from Edmonton to the highest bidder.
Yes, the smart money always suggested he would stay in Edmonton. But that doesn`t mean the rest of us can`t feel a little disappointed that he left all that excitement – along with over $100 million in potential free-agent earnings – on the table.
WINNER: Stan Bowman
McDavid`s decision on Monday to sign a two-year extension with the Oilers came after months of deliberation about whether, and for how long, he wanted to commit to Edmonton. A key part of this process involved meetings with General Manager Stan Bowman to understand the GM`s strategic plans for the Oilers` future. Ultimately, they succeeded in retaining him as an Oiler for several more attempts at the Stanley Cup.
One might argue that the pitch only convinced McDavid to stay for two more seasons, which could be seen as less than fully effective. One could also suggest that by essentially freeing up cap space, McDavid should gain more influence over organizational decisions. However, let`s be realistic: no franchise player typically wields that level of power within an organization.
On an unrelated note: Congratulations to Oilers coach Kris Knoblauch, who coached McDavid in junior hockey, on his new contract. This contract was awarded by Jeff Jackson, the CEO of hockey operations, who formerly served as McDavid`s agent.
LOSER: The Oilers` Timeframe for Success
Now comes the difficult challenge: constructing a team around McDavid and fellow Oilers star Leon Draisaitl that can finally secure a Stanley Cup championship. Alternatively, if that goal isn`t met, the task is to convince McDavid that Edmonton`s future is promising enough for him not to depart in 2028.
Frankly, the former scenario (winning a Cup) appears more probable than the latter (convincing him to stay without a Cup).
The reigning Western Conference champions largely retain the same roster as last season, though the departure of Corey Perry might affect their Stanley Cup Final “karma.” Looking ahead, Bowman will have significant cap space available next summer due to a rising cap ceiling, including contracts for both goaltenders.
McDavid has effectively become “Uncle Jimmy” from Season 4 of `The Bear,` setting a countdown clock for the restaurant`s success or failure. Bowman will spend the next three years frantically searching for the right ingredients to perfect the team`s recipe.
WINNER: General Manager Empowerment
Every NHL general manager has, at some point, attempted to persuade a player with an expiring contract to accept slightly less than market value to benefit the team in a salary-capped league. Most often, players are unwilling to be penalized for past management errors; while a small “hometown discount” might occur, star players demand to be compensated accordingly.
Sidney Crosby was once the benchmark for contractual sacrifice, maintaining an $8.7 million AAV since the 2008-09 season. Back then, this represented 15.3% of the salary cap; on his most recent extension, it`s 9.1% of the cap. As of now, McDavid is set to earn 12.0% of the cap in 2026-27, though this percentage could still decrease.
His deal is so team-friendly that he isn`t even the highest-paid player on the Oilers. Every GM in the league will undoubtedly echo in unison: “Be like Connor.”
Should the Oilers achieve a championship during this two-year period, they will also have a proven concept for this approach.
LOSER: NHLPA
Whenever a player chooses to accept less than their market value, it generally doesn`t contribute to improving overall player salaries.
While the NHLPA was undoubtedly pleased that Kirill Kaprizov managed to secure an even better offer from the Minnesota Wild – settling for a league-record $136 million total value and a $17 million AAV over an eight-year term –
one can only imagine the astounding figures McDavid could have commanded as the most coveted free agent in hockey history, rather than maintaining his current cap hit for two more seasons.
WINNER: Leon Draisaitl
As previously reported this year, Draisaitl`s decision to sign an eight-year contract extension through 2033 didn`t guarantee McDavid`s long-term commitment to the Oilers.
However, as it stands, Draisaitl is assured of playing alongside McDavid, receiving passes from him for at least the next three seasons. This is a significantly better outcome than merely having him for the 2025-26 season, which was a distinct possibility as McDavid pondered his future as a pending unrestricted free agent.
It`s not perfect, but it`s far from catastrophic. And surprisingly, he`s still the highest-paid player on the Oilers! Who would have predicted that?
LOSER: Auston Matthews
Among all the potential destinations for McDavid, none would have caused as much upheaval in the hockey world as the Ontario native taking his talents to the Toronto Maple Leafs. A dynamic one-two punch of McDavid and Matthews might have convinced even the most cynical Leafs fans that the team could finally 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 for any potential opportunity to play with McDavid… when both are unrestricted free agents… and coincidentally share the same agent. Now that truly promises to be an interesting summer.
WINNER: McDavid`s Legacy in Edmonton
Assuming he completes the full term of this contract, McDavid will have dedicated 13 years of his life to Edmonton – a journey that began when a series of draft lottery balls fortuitously landed in the Oilers` favor in 2015 – all in pursuit of the Stanley Cup.
He has propelled the team to two consecutive Cup Finals and three Conference Finals overall, reaching a point where he became only the second skater in NHL history to earn the playoff MVP award in a losing effort. While two additional seasons might not fully satisfy some Edmonton fans, especially after Draisaitl committed for eight more seasons last September,
the majority of fans likely view this as McDavid keeping their championship window open by foregoing a vast fortune in potential free-agent earnings and providing the Oilers with crucial cap flexibility. If he chooses to leave in 2028, it won`t be seen as abandoning Edmonton; rather, it will be after giving the franchise his absolute best. If it concludes without a Cup, the responsibility for squandering this opportunity will fall squarely on the Oilers` legacy.
LOSER: The State Income Tax Debate
The advantages for teams playing in states without income tax have been frequently reiterated and hotly debated, particularly since the Tampa Bay Lightning, Florida Panthers, and Vegas Golden Knights began lifting the Stanley Cup. Players like Brad Marchand have highlighted how the absence of state income tax enables teams to maintain roster consistency and attract top talent.
However, this factor did not entice McDavid on his current contract. As Panthers executive Roberto Luongo humorously tweeted, this decision doesn`t exactly fuel the intensity of this ongoing debate:
He might still end up playing in Florida, Las Vegas, or Dallas once this contract expires. But for now, he has 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 consecutive Stanley Cup over the Oilers for that debate to reignite…
Duncan Priestley