Edmonton Oilers insider Bob Stauffer has provided a major update on superstar Connor McDavid’s contract extension timeline, revealing negotiations are expected to pick up immediately after teammate Leon Draisaitl’s wedding

Bob Stauffer, the ever-informative insider and voice of the Edmonton Oilers, has recently offered fans and media a glimpse into what could be one of the most closely watched contract extensions in recent NHL history: Connor McDavid’s. The news, while not an official announcement, has ignited a wave of speculation and excitement throughout the Oilers’ fanbase and the greater hockey world. According to Stauffer, significant movement on McDavid’s contract extension is expected to begin immediately after teammate Leon Draisaitl’s wedding, which has brought an additional layer of intrigue to the proceedings.

For Oilers fans, McDavid’s future has been the subject of constant conversation since he signed his current eight-year, \$100 million contract in 2017. At that time, the deal made McDavid the highest-paid player in the NHL, and his stock has only risen since then. Now, with just a few years left on that contract, all eyes are on the star forward to see what his next move will be. Would he re-sign with Edmonton? Would he explore free agency? What kind of financial commitment will the Oilers have to make to keep the best player in the world?

The timeline that Stauffer shared offers fans and analysts alike some sense of clarity, although it remains shrouded in mystery. Draisaitl’s wedding is the next big event on the Oilers’ social calendar, and according to Stauffer, it is likely to serve as a marker for when the real discussions around McDavid’s contract will take shape. The wedding, an event that will no doubt draw the attention of the Oilers’ leadership, is also a crucial piece of the offseason puzzle, as it offers a clear timeline for when attention can fully shift to McDavid’s future. For a team as closely-knit as the Oilers, the off-ice dynamics, including personal milestones like Draisaitl’s wedding, can play an important role in how business is conducted.

As with most major contract negotiations, timing is everything. For McDavid, whose deal is up after the 2025–26 season, it’s not just a matter of agreeing to terms—it’s about creating a partnership that will benefit both the player and the franchise for the long term. McDavid, as one of the most dominant players in the NHL, has earned the right to test the market, and there is little doubt that he will receive offers from various franchises. However, there are a few key factors that suggest McDavid’s heart is still very much with Edmonton, even if the financials are part of the equation.

First, let’s consider McDavid’s legacy with the Oilers. Since being drafted first overall in 2015, McDavid has become the face of the franchise, a player who transcends the game itself. He’s been a constant source of joy for Oilers fans, and a future Hall of Famer who has redefined what it means to be a franchise player. In many ways, McDavid has already cemented his place in Edmonton’s storied history, with the 2017 Hart Trophy and numerous league-leading point totals highlighting just how exceptional he is. His presence on the ice has pushed the Oilers into a new era, and the team’s performance on the ice has seen a corresponding improvement, with playoff appearances becoming more frequent in recent seasons.

Despite all this, McDavid is still in search of the one thing that has eluded the Oilers since their last Stanley Cup win in 1990: a championship. The team has made it to the Western Conference Final in recent years but has fallen short of reaching the ultimate prize. McDavid’s desire to win is not a secret; it’s part of what fuels his relentless work ethic and makes him such a unique player. For many, the question becomes: will McDavid’s desire for a championship lead him to a different franchise, one that might be closer to immediate contention? That’s a question that fans, management, and McDavid himself will all have to grapple with as negotiations begin.

The key to retaining McDavid, then, might not just be offering him a lucrative financial deal but creating a competitive team around him—one that can finally break through and capture that elusive Stanley Cup. The Oilers have the tools to do that. With McDavid leading the charge, Leon Draisaitl as his right-hand man, and a supporting cast that includes the likes of Ryan Nugent-Hopkins, Zach Hyman, and others, the team is well-positioned to compete for a championship. But the Oilers need to prove that they can put together a deep, balanced roster that can take on the league’s elite.

In many ways, the path to securing McDavid’s long-term future is as much about on-ice success as it is about financial negotiation. The Oilers need to show McDavid that they are not just a team built around him, but one that can elevate his chances of winning that elusive Cup. If the Oilers can continue their upward trajectory and make a legitimate push for a title, McDavid may be more inclined to sign on the dotted line.

Financially speaking, McDavid is expected to sign another massive deal, likely eclipsing his previous contract in both length and dollars. How much the Oilers are willing to offer and what kind of cap space they will have available remains to be seen. The NHL’s salary cap situation is always a challenge for teams, and the Oilers have already committed significant money to McDavid’s counterpart, Leon Draisaitl. Both players are worth every penny, but the team’s ability to balance its books while building a competitive roster will be a key consideration.

From McDavid’s perspective, however, it’s not just about the money. While it’s widely accepted that McDavid will likely become the highest-paid player in the league once again, there are other factors at play. The opportunity to compete for a Stanley Cup, the stability of the Oilers’ management team, and the overall direction of the franchise are equally important considerations. Oilers management, led by general manager Ken Holland, will need to demonstrate that the team is on the right path and that McDavid’s pursuit of a championship can be realized in Edmonton. That’s the challenge that Holland and the rest of the front office face over the next few months.

Another point worth considering is McDavid’s relationship with the city of Edmonton. The Oilers and the city share a special bond. McDavid has become not just a hockey icon in Edmonton but a beloved figure in the city’s fabric. Whether he’s at a local restaurant, walking through the streets, or participating in community events, McDavid is embraced by fans who feel a deep connection to him. This emotional bond can’t be ignored in the decision-making process. While the allure of playing for a major market might be tempting for some players, McDavid has consistently expressed how much he enjoys playing in Edmonton and how important the fans are to him.

So, what exactly will McDavid’s next contract look like? While the details remain unclear, one thing is certain: it will be a monumental moment for the Oilers. Whether he signs a max-term deal for another eight years, or something shorter that gives him more flexibility to explore free agency down the road, McDavid’s extension will define the future of the franchise. The franchise is at a crossroads, and securing McDavid for the long haul would provide the stability and foundation needed to build a true championship contender around him.

What does all of this mean for the Oilers’ fanbase? For years, McDavid has been the shining light in a franchise that has experienced more than its share of struggles. Fans have witnessed the highs of McDavid’s individual performances—his stunning goals, his playmaking brilliance, and his consistent excellence. But they have also seen the team falter in the playoffs year after year. The stakes of McDavid’s next contract are incredibly high, not just for the team’s future, but for the identity of the franchise as a whole. Fans are invested, perhaps more than ever, in ensuring McDavid remains the face of the Oilers for years to come. But there is also a sense of optimism that the Oilers can continue to build the kind of team that McDavid will want to stay with.

In the coming weeks, as the focus shifts to McDavid’s future, there will no doubt be a great deal of speculation, rumors, and anticipation surrounding his decision. But for now, with Stauffer’s update that negotiations will pick up after Draisaitl’s wedding, fans can at least take comfort in knowing that the process is moving forward. Whether McDavid stays with the Oilers for the long term or chooses a different path, one thing is clear: his future in Edmonton is not just about the money—it’s about winning.