The Edmonton Oilers are in the midst of a battle in the Stanley Cup against the Florida Panthers. While they are attempting to win the Stanley Cup, it's never too early to look at the summer. The Oilers' nightmare scenario in NHL free agency could see them struggle to retain Connor McDavid while losing much of the depth that helped them win two straight Western Conference titles.
The Oilers certainly have a dream scenario that includes entering the 2025 NHL free agency period as Stanley Cup champions and re-signing key players. However, the Oilers may not have it so easy either. No, they might be coming into this offseason with another Stanley Cup loss and the feeling of helplessness at failing to secure a cup.
Edmonton has decisions to make, especially with roughly $11.9 million in cap space. Additionally, they may not find it as easy to return to the Stanley Cup a third time, especially if they fail to achieve a few of their objectives. It all starts with the best player on the planet, and how the extension they give him could change everything.
The Oilers don't re-sign Connor McDavid
Connor McDavid is currently focused on the Stanley Cup and isn't thinking about his future contract. However, like an overarching antagonist in an epic trilogy, it lingers, and it will certainly come to the forefront shortly. The facts are simple. McDavid will become an unrestricted free agent next offseason. But will the Oilers let it get that far?
The Oilers extended Leon Draisaitl last offseason, but it took until September to finalize the deal. While many hockey experts and fans alike don't expect McDavid to become a free agent, the uncertainty could cloud the Oilers, especially as they potentially try to return to the Stanley Cup. Edmonton must re-sign its superstar sooner rather than later.
The absolute worst-case scenario for Edmonton would be for this to linger into the 2025-2026 season. McDavid probably would not hold on, but playing in a contract year would not be ideal. Currently, they are paying him just over $12 million. The Oilers likely will give him a raise. It's not a matter of if, but a matter of when. If the Oilers let this drag out, it could derail their title chances next season.
The Oilers don't match the offer for Evan Bouchard
Evan Bouchard could find a new home, and certainly has a choice to make during the NHL free agency period. Ultimately, he is the second-most important player during the Oilers' free agency period.
Bouchard is a restricted free agent. Thus, that means the Oilers have the first rights to his contract. Many expect the Oilers to re-sign Bouchard. But what happens if another team matches their offer, or even beats it? Could Bouchard leave Edmonton for greener pastures? There is a chance it could happen, and the Oilers must find a way to keep their star defenseman.
Edmonton loses depth in NHL free agency
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Lost in the midst of extending McDavid and retaining Bouchard is all the depth the Oilers possibly stand to lose during NHL free agency. Trent Frederic, Corey Perry, and Kasperi Kapanen are free agents this summer. All have contributed in some way throughout the Stanley Cup Playoffs.
There is also the possibility that the Oilers will lose these players and others in the future. Notably, Evander Kane, Adam Henrique, and Viktor Arvidsson stand to become NHL free agents next offseason. The Oilers have mostly patched up their secondary lines with veteran players over the years and have not developed anyone in their bottom six.
McDavid, Draisaitl, Zach Hyman, and Ryan Nugent-Hopkins have made this team very top-heavy. Yet, the Oilers might lose the depth required to sustain their success.
The Oilers don't find a goalie through NHL free agency
There was a time when many thought the Oilers would trade for John Gibson to cement their final piece, finally. Instead, they did nothing and simply went with Stuart Skinner and Calvin Pickard in the Stanley Cup Playoffs.
There were times when it looked like a good choice, as Skinner posted two consecutive shutouts in the second round against the Vegas Golden Knights. Then, there were times when it looked horrible, such as the first round against the Los Angeles Kings, when he allowed six goals on 30 shots in Game 1 and five goals on 28 shots in Game 2.
The Oilers need a long-term answer in the net. So far, the combination of Skinner and Pickard has been very inconsistent. It's become so bad that it may cost them another Stanley Cup Final. The nightmare scenario in Edmonton would be to ignore the goaltending woes once again.