After months of intense speculation, Connor McDavid officially signed a contract extension with the Edmonton Oilers this Monday. However, this agreement, a remarkably team-friendly two-year deal with an average annual value (AAV) of $12.5 million, doesn`t put an end to all discussions about his future. Instead, it means the world`s premier hockey player could still become the most sought-after unrestricted free agent in NHL history by the summer of 2028.
For the Edmonton Oilers, this situation is definitely viewed with optimism. More precisely, they are focused on the prospect of a half-full Stanley Cup. With McDavid committed for at least three more seasons, the franchise gains additional opportunities to secure its first championship since 1990.
As is customary with any major decision in the National Hockey League, this contract extension inevitably creates both beneficiaries and those who are disadvantaged. Below is an analysis of the key outcomes stemming from Connor McDavid`s new deal:
WINNER: Connor McDavid
While a shorter extension will undoubtedly lead to ongoing questions about why he chose this term and what it signifies for his ultimate future in Edmonton, McDavid can now set those concerns aside. With this deal finalized before the NHL season even started, he is free to concentrate entirely on his immediate goals: bringing a Stanley Cup to Edmonton and securing a gold medal for Canada. Such long-term questions can safely be deferred until at least September 2027, suggesting that McDavid himself desired this clarity before the puck dropped.
LOSER: Sidney Crosby
With McDavid`s contractual status resolved, 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 has reportedly grown weary of discussing, yet the speculation is bound to intensify with every Penguins loss – and many pundits are forecasting a challenging season for Pittsburgh. Previously, McDavid`s looming unrestricted free agency offered a partial distraction from Crosby’s situation. Now, he stands as the primary catalyst for the season`s rumor industry.
The rumor mill is expected to intensely focus on potential Sidney Crosby trades, especially with McDavid`s contract now settled for two seasons.
WINNER: Edmonton Fans
For a long time, the sentiment among Oilers fans that McDavid would remain in Edmonton often sounded more like hopeful aspiration than firm conviction. There were underlying fears that the current season might be their last shot, or that McDavid might yearn for one of the NHL`s more glamorous franchises, perhaps one perceived to have a more sustainable championship window than Edmonton`s. Haunting memories of past star departures, such as Wayne Gretzky moving to Los Angeles, resurfaced – particularly given rumors that the Kings were indeed preparing salary cap space for McDavid next summer. Yet, he chose Edmonton. While not a long-term commitment at this moment, he nonetheless chose to continue living and playing there, driven by the profound desire to deliver a championship to the city.
LOSERS: Everyone Else
The absence of a prolonged McDavid rumor mill, the lack of a free agency frenzy, and the dashed hopes of him arriving in major markets like New York, Dallas, Los Angeles, Tampa Bay, or even Toronto to instantly transform those teams into Stanley Cup favorites is a disappointment for many. The thrilling narrative of McDavid potentially taking his talents to the highest bidder, accompanied by the dramatic “Imperial March” soundtrack, will not materialize. While conventional wisdom always suggested he would stay in Edmonton, it’s understandable for the wider hockey world to feel a little let down by missing out on all that potential excitement – not to mention the spectacle of him potentially commanding over $100 million in free agency.
WINNER: Stan Bowman
Connor McDavid`s decision to sign a two-year extension with the Oilers on Monday came after a period of deep contemplation about his commitment to Edmonton. A significant part of this process involved discussions with General Manager Stan Bowman, during which Bowman outlined his long-term vision for the Oilers. Ultimately, Bowman’s efforts helped secure McDavid for several more attempts at the Stanley Cup. Some might argue that a two-year deal doesn`t fully reflect the effectiveness of Bowman`s persuasion, or that McDavid`s financial concession should grant him greater influence over organizational decisions. However, no franchise player truly wields that level of power within an NHL organization. On a separate note, congratulations are in order for Oilers coach Kris Knoblauch, who previously coached McDavid in juniors, on his new contract. This contract was reportedly given to him by Jeff Jackson, the CEO of hockey operations and notably McDavid`s former agent.
LOSER: The Oilers` Runway
The true challenge now begins for the Oilers: building a championship-winning team around their dynamic duo of McDavid and Leon Draisaitl. The objective is twofold: either to finally hoist the Stanley Cup, or to convincingly demonstrate to McDavid that Edmonton’s future is sufficiently promising for him to stay beyond 2028. Frankly, the former seems more probable than the latter. The team, which reached the Western Conference Final last season, largely retains its core roster, although the departure of Corey Perry might subtly impact their Stanley Cup Final “karma.” Looking ahead, GM Bowman will have a substantial amount of cap space available next summer, particularly with both starting goaltenders’ contracts expiring. McDavid’s extension essentially acts as a countdown clock, akin to Uncle Jimmy in “The Bear,” putting immense pressure on Bowman to frantically piece together the right ingredients to find the winning recipe within the next three years.
Despite being two of the NHL`s elite talents, Leon Draisaitl and Connor McDavid have yet to secure a Stanley Cup.
WINNER: GM Empowerment
Every NHL general manager has, at some point, attempted to convince a star player with an expiring contract to accept a slightly lower salary to help the team navigate the constraints of a salary-capped league. More often than not, players firmly resist becoming victims of past management contractual errors; while a small hometown discount might be offered, stars typically demand to be paid their market value. Historically, Sidney Crosby served as the prime example of contractual sacrifice, maintaining the same $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 accounts for 9.1%. As of now, McDavid’s deal means he will earn 12.0% of the cap in 2026-27, though this percentage could still decrease. His contract is so team-friendly that he isn`t even the highest-paid player on the Oilers. This sets a powerful precedent, and general managers across the league will undoubtedly echo the mantra: “Be like Connor.” Should the Oilers achieve a championship during this two-year window, they will have tangible proof of concept to support this approach.
LOSER: NHLPA
Whenever a player chooses to accept less than their true market value, it inevitably ripples through the league, failing to bolster the collective bargaining position of other players. While the NHLPA undoubtedly celebrated Kirill Kaprizov’s success in securing an improved, record-breaking offer from the Minnesota Wild – culminating in the highest value ($136 million) and AAV ($17 million over eight years) in league history – the mind boggles at the astronomical figures McDavid could have commanded. As the most coveted free agent in hockey history, his potential earnings, had he waited to hit the open market, would have far surpassed his current cap hit for these two additional seasons.
WINNER: Leon Draisaitl
As previously reported, Draisaitl’s decision to sign an eight-year contract extension through 2033 did not automatically guarantee McDavid’s long-term commitment to the Oilers. However, with this new agreement, Draisaitl is now assured of receiving passes from McDavid for a minimum of three more seasons. This is a significantly better outcome than potentially having him for just the 2025-26 season, which was a distinct possibility as McDavid deliberated his future as a pending unrestricted free agent. While not the absolute ideal scenario, it is far from catastrophic. And, surprisingly, he still holds the distinction of being the highest-paid player on the Oilers! Who could have predicted that?
LOSER: Auston Matthews
Of all the hypothetical landing spots for Connor McDavid, none would have sent a more seismic shockwave through the hockey world than the Ontario native taking his immense talents to the Toronto Maple Leafs. A formidable one-two punch of McDavid and Matthews might have finally convinced even the most cynical Leafs fans that the team could genuinely win its first Stanley Cup since 1967. Alas, with McDavid`s extension and Mitch Marner’s departure to the Golden Knights earlier in the offseason, Matthews will have to wait until the summer of 2028 for any potential dream pairing. Coincidentally, that`s when both players are slated to become unrestricted free agents and, remarkably, share the same agent. That summer indeed promises to be quite interesting.
For the foreseeable future, Connor McDavid and Auston Matthews will continue to play for separate teams on opposite sides of the continent.
WINNER: McDavid`s Legacy in Edmonton
Assuming he completes the full term of this extension, Connor McDavid will have dedicated 13 years of his life to the Edmonton Oilers – a journey that began after a fortunate bounce of draft lottery balls in 2015 – all in pursuit of the Stanley Cup. He has already elevated the team to two consecutive Cup Finals and three conference finals appearances overall, even earning a playoff MVP award despite his team losing. While some Edmonton fans might still harbor reservations about only two additional seasons, especially compared to Draisaitl’s eight-year commitment, the majority likely view this as McDavid actively keeping the contention window open. He has done so by foregoing a Scrooge McDuck-esque money bin of potential free agent riches, thereby granting the Oilers crucial added cap flexibility. If he chooses to depart in 2028, it will be after giving his absolute all to the franchise. Should a Cup not materialize, the blame will largely fall on the Oilers for squandering his generational talent, not on McDavid for abandoning them.
LOSER: The State Income Tax Debate
The perceived advantages for NHL teams located in states without income tax have been a constant source of debate and discussion, particularly since the Tampa Bay Lightning, Florida Panthers, and Vegas Golden Knights began consistently lifting the Stanley Cup. Players like Brad Marchand have publicly noted how the absence of state income tax enables teams to maintain roster consistency and attract top talent. However, McDavid’s decision to sign his current contract with Edmonton, where the provincial income tax rate is 15%, doesn`t support this argument for his immediate future. While he might still end up playing in Florida, Las Vegas, or Dallas once this contract concludes, his current commitment to Alberta temporarily dampens the fervor of this ongoing issue. This debate will undoubtedly reignite with full force if the Panthers manage to win a third consecutive Stanley Cup against the Oilers…
