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Jun 6, 2025; Edmonton, Alberta, CAN; Edmonton Oilers center Leon Draisaitl (29) reacts with center Connor McDavid (97) and defenseman Evan Bouchard (2) after scoring a goal against the Florida Panthers during the first period in game two of the 2025 Stanley Cup Final at Rogers Place. Mandatory Credit: Walter Tychnowicz-Imagn Images

Oilers Are Running Out of Chances to Win a Stanley Cup

Originally posted on The Hockey Writers | By Dale Bochon | Last updated Sep 12, 2025 3:50 PM ET

You can feel the tension in the City of Champions these days. With every passing day that Connor McDavid remains unsigned, it feels like the stress continues to build. Knowing that the NHL salary cap is expected to rise in the next few seasons, it’s hard not to blame McDavid for taking his time to think about his future.

I personally think one of the main reasons Kirill Kaprizov hasn’t signed a new deal with the Minnesota Wild is he also wants to see how much salaries will escalate over the next few seasons. With McDavid pondering his future as he enters the prime of his career, Leon Draisaitl turning 30 this October, and older Oilers such as 35-year-old Mattias Ekholm expressing an interest in re-signing in Edmonton, it’s hard not to see that the future is now for this current group of Oilers. It goes without saying that Oilers general manager (GM) Stan Bowman knows this and will do anything he can to help the Oilers achieve their goal of winning the Stanley Cup. But it won’t be easy.

Oilers Are the Oldest Team in the NHL in the 2024-25 Season

Last season, the Oilers were clearly the oldest team in the NHL with an average age of 30.1. After losing 40-year-old Corey Perry, Evander Kane (34), Jeff Skinner (33) and 32-year-old Viktor Arvidsson in the offseason, the Oilers are looking to youth such as Matthew Savoie (21) and Ike Howard (21) to interject some speed and energy into the lineup. But will it be enough in 2025-26? As the veteran core, which includes McDavid, Draisaitl, Ekholm, Ryan Nugent-Hopkins (32), Zach Hyman (33), and Darnell Nurse (30), get older, it’s so obvious that the Oilers need to win within the next two to three seasons before the window closes.

Will two to three years be the contract McDavid signs with the Oilers? I’m guessing it will be. If the team can’t put it together and win a Stanley Cup Championship within this time frame, I wouldn’t blame McDavid for wanting to go elsewhere to find a team where he can win it all.

Oilers Management Can’t Afford Any More Missteps

It’s now feeling more and more like former Oilers GMs during the McDavid era really lost the plot. Both Peter Chiarelli and Ken Holland moved the team forward, but not at the pace required to win. Both former GMs left Bowman with a tall task of plugging holes, managing an almost unmanageable cap situation, and finding a legitimate Stanley-Cup-calibre goaltender. It’s almost as though Chiarelli and Holland felt they had all the time in the world, but now we’re at the 11th hour, and sorry to say time is running out on the Oilers.

The Best-Case Scenario Is to Win It All This Season

Now that it’s really crunch time in Oil Country, if you’re a fan, you have to hope that the Oilers can finally get over the hurdle and win the Stanley Cup this season. If they do, I believe there’s an excellent chance that McDavid will finish out his career in Edmonton. The same holds true for Draisaitl. As a lifelong Oilers fan, it’s tiring to see Hall of Famers and great players come and go and never finish out their careers here. The list is long, from Wayne Gretzky and Mark Messier to Jari Kurri and Doug Weight. It would’ve been nice to see them play their entire careers in Edmonton. With an owner like Daryl Katz, money isn’t the issue like it was with previous Oilers ownership. It’s now up to Bowman and Oilers CEO of Hockey Operations Jeff Jackson to win now. It’s a bit tiring as an Oilers fan to always have a threat of a great player leaving.

Maybe knowing that they’re getting close to the midnight hour, Oilers management will try to move heaven and earth this season to win. That could very well mean Oilers fans get to watch McDavid in Oilers silks for the rest of his career and the City of Champions moniker gets another invigorating reset. Either way, if you’re an Oilers fan, you have to hope that it all comes together now.