Oilers Need To Win Before Contracts Kick In And Big Decisions Are Required

The Oilers have some big contracts coming and with the cap news this week, it's even more important they win now.

The Edmonton Oilers have always known their window to win was only going to be so big. Former GM Ken Holland alluded to making that window as wide as possible, and new GM Stan Bowman has even less time to produce a winner.  

This is an Oilers team that has the key pieces. They've got the star power at the top of their lineup. The team has a solid blueline but is working to improve it with additions like John Klingberg and Ty Emberson on low-cost contracts. Their goaltending is doing what it's supposed to. 

All that said, if the Oilers don't capitalize, they could be in trouble. 

With Leon Draisaitl's new contract kicking in next season, he will no longer be on a team-friendly deal. He's currently out-producing his contract, but that may not be the case moving forward. 

Connor McDavid needs a new deal after 2025-26, and the new salary cap estimates suggest he'll get at least $15 million, if not more, on an eight-year deal. He's worth whatever he's paid, but eventually, the Oilers will be out of his prime years and paying him handsomely. 

Evan Bouchard is due for a significant raise. The Oilers might not yet know how to approach his extension, but at some point, he's getting paid, and it won't be cheap. 

These aren't the only big decisions set to impact this team. 

History has shown the advantage of winning before star players cash in on new deals. The Colorado Avalanche lifted the Stanley Cup while Nathan MacKinnon was still on a $6.3 million AAV contract. The Florida Panthers won before handing out major extensions to Sam Reinhart and Carter Verhaeghe. Even the Tampa Bay Lightning, after winning back-to-back Cups, did so before being forced to shed key depth pieces due to cap pressures.

The Oilers face a similar challenge. When Draisaitl, McDavid, Bouchard and Darnell Nurse all make $9 million per season or more, the big jumps projected in the cap ceiling will only go so far. Yes, deals for Zach Hyman and Ryan Nugent-Hopkins will look progressively better, but the rest of the roster needs to come together. 

Edmonton’s ability to retain depth players or attract free agents who want to win will exist (and arguably now better than ever), but the Oilers will be fighting with big money from other teams. Getting impact depth forwards and defensemen at value rates is crucial for a deep playoff run. It will get more challenging as each and every summer goes by.

Forget rumors that the Oilers might pursue a star like Mikko Rantanen next summer. The thing to focus on is the now and the roster being as strong as possible with the contracts that offer a positive ROI. 

The hope is that John Klingberg can vastly outplay the $1.75-million cap hit he takes up. Edmonton needs to see Ty Emberson step up while he's a $950,000 Group 6 UFA. Brett Kulak is a home run at $2.75 million, as is Stuart Skinner at $2.6 million and Calvin Pickard at $1 million. 

If the Oilers can use Evander Kane as an LTIR option, returning for the playoffs without a cap penalty, all the better. 

Rely on Corey Perry to keep doing what he's doing for $1.15 million. Then, hope Connor Brown finds the same magic he did last post-season and at the low cost of $1 million. 

For Edmonton, the message is clear: the time to win is now. Anything short of a championship this season will make the road ahead significantly tougher.

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