Oilers Worried Over “Double Whammy” Disaster Amid Draisaitl Talks – The Hockey Writers Edmonton Oilers Latest News, Analysis & More

With the NHL offseason officially underway for all 32 teams, the Edmonton Oilers face a pivotal decision just days after losing Game 7 of the Stanley Cup Final. This decision could define their future, as a potential contract extension for Leon Draisaitl can be finalized quickly or talks can go sideways, which in turn could lead to problems negotiating with Connor McDavid. Previous reports have the Oilers and Draisaitl camp discussing a new deal with Draisaitl looking for a long-term extension. At the same time, nothing is done, nor can it be signed until July 1.

A new report by Chris Johnston of The Athletic suggests there’s at least some concern about what happens if that deal isn’t finalized right away. So too, he’s not confident those alleged conversations have gotten all that serious.

A Draisaitl Extension Is a Priority and Hopefully Not a Problem

Draisaitl’s current contract, widely regarded as one of the most team-friendly in the NHL, is set to expire in 2025. As of next Monday, the forward is eligible to sign an extension with the Oilers. According to Johnston, Edmonton is unwilling to let the situation drag out and loom over the team like a dark cloud next season.

He writes:

Edmonton is not inclined to let the 28-year-old center simply play out the final year of his contract and walk directly into free agency next July, according to multiple league sources familiar with the front office’s view of the situation.

source – ‘What I’m hearing about Leon Draisaitl and the offseason decision that could blow up the Oilers’ – Chris Johnston – The Athletic – 06/25/2024

Allowing Draisaitl to enter free agency in July 2025 without a new deal would be a significant risk, especially with McDavid’s contract extension eligibility looming a year later. How long the Oilers are prepared to wait past July 1 isn’t clear, but they believe letting Draisaitl enter into the 2024-25 season without an extension is too risky. They may be prepared to move if Draisaitl forces their hand.

Johnston suggested that the Oilers’ management is acutely aware of a “double whammy” scenario. If Draisaitl were to leave as a free agent without a contract in place, it could destabilize the team just as McDavid prepares to determine his fate. It would be bad enough to lose Draisaitl and not get a significant return. To lose both players and let them walk would be crippling and set the franchise back years.

Johnston isn’t suggesting the Oilers think this will happen. That said, the feeling is they aren’t prepared to take that chance and let the dominos start falling. Any signs of hesitation or a feeling they may lose Draisaitl might mean shopping around and seeing what their options are.

The Impact of Playoff Disappointment

The Oilers’ recent Game 7 loss in the Stanley Cup Final adds another layer of complexity. This heartbreaking defeat could either fuel Draisaitl and McDavid and increase their desire to win in Edmonton or make them consider exploring opportunities elsewhere. These two have always talked about wanting to finish what they started. They didn’t do it this season and it’s hard to know if they’ll get this good a chance again. How confident is Draisaitl that the Oilers can get back there? If he isn’t, what is McDavid thinking?

Related: Was McDavid Wrong to Not Accept the Conn Smythe Trophy?

Like Elias Pettersson did in Vancouver, there is the possibility that Draisaitl might prefer to wait and see how the next season unfolds before committing to a long-term contract. The issue is that waiting means more time to converse with McDavid about a possible future outside of Edmonton. The Oilers are not willing to play that game. They cannot set a precedent that might influence McDavid’s decision-making process, nor can they allow these two to maneuver and set up a situation to stick together in another market.

If Draisaitl and McDavid are hungrier to win in Edmonton because they got extremely close but fell short by one goal, perhaps Draisaitl signs immediately. His plan might be to heal from his nagging health issues, focus, and get back to work. Maybe he takes his rumored extension between $13 – $14 million per season and says thank you very much on July 1. Perhaps McDavid will do the same on July 1, 2025.

If this drags out and Draisaitl isn’t sure, the delay poses issues for the Oilers. The Oilers need to know how much of their salary cap is going to Draisaitl and McDavid. They need to know it right away so they can start preparing ASAP and fill out the roster. Players looking at Edmonton may want to know what Draisaitl and McDavid are doing too.

If the Oilers sense any hesitation from Draisaitl, they must be prepared to explore trade options. Additionally, they must keep an eye on McDavid’s situation, ensuring that their actions with Draisaitl do not negatively impact their chances of retaining their captain.