Oilers’ 2026-27 Season Will Be the Biggest in Franchise History – The Hockey Writers –

The Edmonton Oilers are entering arguably their most important season in franchise history. Connor McDavid will be in his 12th season in Edmonton, and they haven’t won the Stanley Cup. Management continues to fail this team with their poor drafting, salary cap management, and decision-making.

The Oilers had no problem winning back in the 1980s with Wayne Gretzky, Paul Coffey, and Mark Messier. So, why are they having trouble winning with McDavid, Evan Bouchard, and Leon Draisaitl? It’s because management hasn’t improved the goaltending or depth nearly enough, and that’s unacceptable. They’ve had a franchise player for over a decade and haven’t surrounded him with an elite team.

After back-to-back Stanley Cup Final appearances, the Oilers were eliminated in Round 1 by the Anaheim Ducks. Injuries caught up to them, and they have played a ton of hockey over the last few seasons. They needed a break, so an extended offseason is beneficial. They can rest up and come back stronger next season.

The Oilers are a flawed organization. However, that can all change in 2026-27. They finally have salary cap flexibility, and they need to take advantage of that. This is their opportunity to make bold moves. A blockbuster trade should be a necessity because this is their best chance to hoist the Stanley Cup in the McDavid era. Hopefully, they will be a well-rested and motivated group because not winning the Cup isn’t an option.

McDavid Gave the Oilers a Discount

McDavid shocked the world when he signed a two-year contract extension to stay in Edmonton with a $12.5 million cap hit, the same cap hit as his previous contract. It was expected that the Oilers’ captain would get a significant raise on his next deal, but he opted to take a major discount to keep Edmonton’s Stanley Cup window open.

That contract officially begins next season. Now, it’s up to management to use those cap savings to build a true contender around him. This is a crucial offseason because the moves they make could lead to a championship or to McDavid leaving at the end of his contract, if not before.

Management is already off to a poor start since that extension, as they continue to mismanage the salary cap. Since McDavid signed, they inked Jake Walman to a seven-year deal with a $7 million cap hit. They also acquired goaltender Tristan Jarry via trade. He has two years remaining on his deal with a $5.375 million cap hit. He has been putrid this season and is not the upgrade they needed between the pipes. General manager Stan Bowman got into this mess, and he needs to find a way out.

The Oilers also have to decide the futures of Darnell Nurse and Trent Frederic. They are both severely overpaid for what they provide. They both have no movement clauses, so trading them will be difficult. Nurse’s contract is the main reason McDavid hasn’t won a Stanley Cup.

Despite those contracts, the Oilers still have a projected $16.49 million in cap space according to PuckPedia. That’s with nine forwards, five defencemen, and one goaltender on the roster. Defenceman Spencer Stastney is a restricted free agent (RFA) and shouldn’t cost much to re-sign since he was healthy-scratched throughout the season. Isaac Howard should also make the team, bringing the forward count to 10. If they re-sign defenceman Connor Murphy, the Oilers will still have enough cap space to acquire an impactful top-six winger. They can also acquire a starting netminder if they find a way to unload Jarry’s contract.

They need to find a way to improve the team this offseason by any means necessary. McDavid gave the Oilers every opportunity to build a Stanley Cup contender, and now it’s time to deliver. The 2026-27 season is a must-win, and it’s truly Cup or bust. If they bust, they risk losing their franchise centre with nothing to show for it.

Will McDavid Demand a Trade if They Don’t Win the Stanley Cup?

This is a legitimate question we have to ask next offseason if the Oilers don’t win the Stanley Cup in 2027. Will he want to stick around for the final season of his deal? Will Edmonton want to trade him for multiple grade-A assets rather than lose him for nothing when he’s an unrestricted free agent (UFA) in 2028? That’s all dependent on how next season plays out.

If the Oilers want to keep their captain after next season and potentially sign him to another contract, they need a Cup parade on their resume.

If the Oilers don’t win the Stanley Cup in the McDavid era, that could be viewed as the biggest managerial failure in NHL history. Keep following The Hockey Writers for all your NHL content throughout the offseason.