Connor McDavid’s new two-year, $25 million extension has done more than just lock up the best player in hockey; it’s sent a clear message. By taking less money than expected, the Edmonton Oilers’ captain has given management a bit of financial breathing room and, at the same time, set a short but urgent two-year window to chase another Stanley Cup.
The $12.5 million annual cap hit is a bargain by superstar standards and gives GM Stan Bowman the flexibility to tinker with the roster. Now the real question is how the Oilers use that extra space. With the 2025-26 season around the corner, they’ll be looking for pieces that can push them over the top come playoff time.
Can the Oilers Turn a Short-Term Deal Into a Stanley Cup Run?
Goaltending still feels like an area that needs shoring up, and adding another reliable top-six forward wouldn’t hurt either. A few names have already started to circulate, but here are the top three.
1] Jeremy Swayman
It’s no secret that Edmonton’s goaltending situation has been shaky in recent years, which is why the Jeremy Swayman rumor won’t go away.
NHL analyst Pierre McGuire recently hinted that the Oilers may have missed their window last year when the Boston Bruins were at odds with Swayman over a new deal. The 25-year-old eventually signed an eight-year, $66 million contract, but McGuire noted that Boston “doesn’t like long, drawn-out negotiations,” suggesting they may have listened to serious offers at the time.
Swayman posted a .892 save percentage last season and has the calm, controlled style that wins playoff games. Pairing him with Stuart Skinner could have given Edmonton the kind of goaltending depth they’ve been searching for since the Cam Talbot years.
That chance may be gone with the Connor Ingram trade, but if Boston’s cap situation tightens or the Bruins stumble, the Oilers could circle back.
2] Thatcher Demko
If there’s one goaltender who could instantly transform Edmonton’s crease, it’s Thatcher Demko. The Canucks netminder recently signed a three-year, $25.5 million extension that keeps him in Vancouver through 2029, but his name continues to pop up in trade conversations, mostly from dreamers north of the border.
Demko is the kind of goaltender who can steal a playoff series. He’s durable, calm under pressure, and thrives in high-volume games.
The issue? Convincing Vancouver to trade within the division would be close to impossible. The Canucks aren’t exactly lining up to help a rival contender. Still, that won’t stop Edmonton’s front office from keeping tabs, just in case Vancouver’s cap situation forces their hand somewhere down the line.
3] Sidney Crosby
And then there’s the big one: Sidney Crosby. It sounds like a fantasy, but if the Pittsburgh Penguins start another season among the bottom of the pack, it’s not unthinkable that Crosby could consider waiving his no-movement clause for one last shot at a Cup.
Pairing him with McDavid and Leon Draisaitl would be a once-in-a-lifetime lineup, a true hockey dream.
Of course, reality kicks in fast. Crosby’s $8.7 million cap hit would require major roster surgery in Edmonton. Moving contracts might be necessary, and Pittsburgh would want something significant in return, maybe even top prospect Matthew Savoie. So while it’s fun to imagine, it’s far from likely.
McDavid’s new deal has given Edmonton both flexibility and a ticking clock. The captain’s willingness to take less money has created an opportunity, but also pressure.
Whether it’s a steady goaltender like Swayman, a bold swing like Demko, or a pipe dream involving Crosby, the Oilers have options. What they do next could define this short championship window and perhaps McDavid’s legacy in Edmonton.
