Oilers superstar Connor McDavid struggled to find the words to describe the team’s 8-3 loss to the Dallas Stars on Tuesday night. The decision dropped the Oilers’ record to 10-10-5 for the season, and McDavid looked defeated during his post-game interview.
The team is grappling with the same issues that have plagued them since McDavid joined the NHL in the fall of 2015. Edmonton’s secondary offensive support for McDavid and Leon Draisaitl is minimal, and their goaltending remains a significant concern. Considering the Oilers have faced these problems for so long, it makes one wonder why a generational talent like McDavid chose to sign on for two more years of this, especially given the bargain he struck when he signed for just $12.5MM a season.
McDavid’s choice to sign with Edmonton before even considering free agency might become one of the biggest “what-ifs” in NHL history. However, McDavid opted for stability in a familiar market, with a team that has been competitive for most of his NHL career.
Ultimately, McDavid decided to stay loyal to the Oilers, but the two-year term seemed like a warning shot to Edmonton. So far, that warning appears to have fallen on deaf ears. The timing of McDavid’s extension was quite unusual. The superstar had a clear route to unrestricted free agency, which could have been one of the most incredible stories in NHL history if it had come to pass.
McDavid had the chance to be the highest-profile player in NHL history to reach free agency since Wayne Gretzky in 1996. He held leverage against the Oilers and could have waited out the season, sparking a bidding war for his services. This would have boosted his star power and changed what a superstar’s career could look like. Instead, McDavid chose familiarity, even though the timing of his decision wasn’t convenient.
McDavid’s signing has delayed his free agency by 24 months, and some people dismiss this decision by arguing that McDavid will still get paid and reach free agency after the salary cap has significantly increased. While both points have some truth, the counterargument is compelling. Instead of becoming a free agent at 29, McDavid will do so at 31. It might seem minor, but many NHLers see their skills decline after 30.
Another factor is that when McDavid finally signs, the new CBA rules on contract length will apply, meaning the maximum deal with his current team will be seven years, and he’ll only be able to land six years on the open market. Although this one-year reduction isn’t a significant issue, it will likely cause McDavid to leave money on the table on his next deal.
In terms of missed opportunities, McDavid would have been the first generational player in NHL free agency to test the market in the prime of his career. While it would have made great theater for the NHL, it would also have been an opportunity for McDavid to shift the league’s balance of power toward whichever team he joined, while helping reset the salary structure for superstar NHLers. McDavid is clearly not a $12.5MM player, but like many top NHLers before him, he took a ‘hometown discount’ to stay with his current team.
For some NHLers, taking that discount has worked out well (Sidney Crosby, Steven Stamkos, Nathan MacKinnon). Far more often, the savings from a reduced salary cap are wasted. Even Crosby, who traded tens of millions of dollars to play on consistently competitive teams, saw many of those seasons marred by costly mistakes on depth players with inflated cap hits (Jack Johnson, Erik Gudbranson, Nick Bjugstad). Crosby essentially subsidized poor roster decisions with his lower cap hits, and would no doubt do so again, given the Stanley Cup championships Pittsburgh has won during his career.
McDavid’s decision to re-sign essentially upholds the NHL’s long-standing tradition of superstars taking less money to stay with their team, and no doubt he did so while feeling loyalty to the Oilers fans who have endured the same heartbreaks he has. The reality is, McDavid has gone through a decade without winning the Cup, despite multiple front-office makeovers, coaching changes, cap mismanagement, and an inability to surround him with real depth. And while the depth has improved over the last few years, the “we’re almost there” mentality won’t put a Stanley Cup ring on McDavid’s finger.
All of this to say, McDavid probably owed it to himself to explore free agency at least to see if a team with a more precise winning blueprint could emerge, giving him a better chance at a title. July 1, 2026, would have offered a window into that, but McDavid chose not to look, and it could come back to haunt him if he never wins a championship. McDavid had all the leverage, which makes his decision baffling, because exploring free agency didn’t require him to leave Edmonton. He could have casually explored his options, had discussions with teams, listened to their pitches, and then re-signed with Edmonton—something that might have pushed the Oilers to step up their game and get creative with their roster. But the Oilers didn’t need to worry about losing McDavid, and it seems this has led to some apathy across the organization, as they don’t seem to be a group hungry to win.
Generational players across all leagues have frequently tested free agency. NBA superstar LeBron James famously took his talents to Miami nearly 15 years ago, and MLB superstar pitcher Paul Skenes will likely follow suit one day. It’s common, and not all players do it because they’re leaving; they do it for a variety of reasons. They can because the process gives them power, and it’s one of the few times they get to fully control their own destiny.
McDavid could have taken a different route, but he didn’t. While he’s given the Oilers a short leash to build a winner around him, he could have kept that leash even tighter, which might have pushed the Oilers to solve their roster issues more quickly. It could also have generated a story that might have become a sensation across all platforms—a broader narrative focusing on a star-driven tale on a smaller scale than MLB superstar Shohei Ohtani’s. The buzz would have been enormous and arguably the biggest NHL story since the Oilers traded Gretzky to the Los Angeles Kings.
Moving on could have been a great branding opportunity for McDavid to become even more mainstream, but he chose the safe, comfortable route in Edmonton. It’s a loyalty decision, and it’s completely understandable given that the Oilers have been close to a title in the last two years and he has built a bond with his teammates. For his legacy, though, he might need to chase greatness in a different city in the next two and a half years.