May 23, 2026 by Ryan Lotsberg

General consensus in the hockey world says that this is the most important Edmonton Oilers offseason in the Connor McDavid era, if not in franchise history. After a first round knockout heading into the first year of the generously discounted two-year extension that McDavid signed with the Oilers last fall, the panic and urgency are at an all-time high in Oil Country. 

The sense is that if the Oilers don’t win the Stanley Cup next year, then McDavid will want to leave. The Oilers can’t let him walk away for nothing in free agency, so many people think that they will have to trade McDavid if they don’t win it all in 2026-27. 

When I’ve read posts from fans on X ever since the Oilers got eliminated, all I have seen is “Cup or bust”, “win now”, and “all in”. Honestly, it drives me INSANE! Even if you think that McDavid is going to walk away after his contract expires or demand a trade in 2027-28 if they don’t win next season, the panicked, aggressive approach doesn’t work. The absolute stupidest thing the Oilers could do this summer would be to let their panic over the worst case scenario about what they think McDavid might do force them into desperate panic moves. They need to prevent the added drama from clouding their judgment.

Having McDavid has added extra pressure to the franchise to accelerate the process of building a winner. That has been the case since they won the draft lottery. Peter Chiarelli was hired by the Oilers six days after they unexpectedly won the 2015 draft lottery. Chiarelli was the biggest and most experienced brand name available at the time. His first move after drafting McDavid was to trade the sixteenth pick for Griffin Reinhart, who Chiarelli foolishly thought to be NHL ready, rather than selecting one of the many available players that went on to become NHL stars.

The next time the Oilers had a chance to make a GM change, they went with Ken Holland, who was once again the biggest and most experienced brand name out there. He eventually got the Oilers to the Stanley Cup Final, but he made several missteps that involved prioritizing the here and now over future success. There’s no other way of putting it other than to say that the drafting and development under Holland was atrocious, and it is costing the Oilers dearly today.

Current GM Stan Bowman was hired after Holland. Once again, he was the biggest and most experienced brand name available. He has been to one Stanley Cup Final with the Oilers, but that was largely Holland’s team. Bowman’s Oilers bowed out in round one this season. I recognize the cap situation he was dealt due to the timing of the Draisaitl and Evan Bouchard raises, but I feel that the poor moves Bowman has made have heavily outweighed the good moves in his first two years as Oilers GM.

Related: 29 + 2 = $12.1 million

The same hiring philosophy reigned supreme for coaches in the early stages of the McDavid era. Todd McLellan and Dave Tippett were the biggest brand names available at the time of their hirings. Ken Hitchcock, another extremely experienced coach, replaced McLellan briefly during the 2018-19 season. I’ll give them credit for deviating from that hiring philosophy with the Jay Woodcroft and Kris Knoblauch hirings. The McDavid era Oilers have had their greatest success with those young head coaches.

My point here is that the biggest and most experienced brand names are rarely the right answer when it comes to management and coaching. They haven’t been throughout the McDavid era, and I’m not sold that it will be the right answer to the current situation at hand in Edmonton.

The “win now” philosophy has done FAR more damage than good for the Oilers from a roster management standpoint as well. Oilers CEO Jeff Jackson was initially praised for signing Jeff Skinner and Viktor Arvidsson to discounted deals on July 1, 2024; but we know how those signings panned out. All of that money could’ve been used to keep Dylan Holloway and Philip Broberg, who played roles in the ‘24 Oilers playoff run and have become important young contributors for the St. Louis Blues.

I understand that Holland offered contracts to Holloway and Broberg while they were in the minors in January of 2024, and I understand that Broberg was already unhappy in Edmonton before that happened. Injuries played a role in the delayed development of both players, but the organization seemingly actively worked to block Broberg at every possible turn. Part of the onus falls on the player to earn his spot, but the Oilers always made the choice to either demote Broberg or put someone else in front of him when they could’ve and should’ve made developing their 2019 eighth overall pick at the NHL level more of a priority. 

Putting Broberg in during the regular season was too much of a risk because of the “win now” philosophy. That line of thinking cost them a young contributor that they could really use now. It also put them in a position where they needed to replace Broberg. They did that by spending their 2026 first round pick on Jake Walman at the 2025 trade deadline. It was an asset that they wouldn’t have had to spend if they had been thinking about the future during Broberg’s development instead of being worried about how developing one young player would destroy their chances of immediate success. As fate would have it, that pick will fall between seventeenth and 24th after the Oilers got knocked out in the first round. That pick was viewed as a “nothing” pick because the expectation was that it would be a late first rounder after another deep playoff run. That’s an incredibly short-sighted and irresponsible opinion.

It goes further back than that though. This feels like a great time to bring up the 2021 draft again. Jesper Wallstedt gave Oilers fans a stark reminder of the mistake that Holland made by trading the twentieth pick of the 2021 draft to the Minnesota Wild to move back two spots and to gain another pick later in the draft when he shut them out on December 2, 2025. Holland wanted Xavier Bourgault rather than an elite goaltending prospect because goalies take too long to develop. Well, here we are five years later, and Wallstedt was the starting goalie on a Wild team that advanced further in the playoffs than the Oilers did, and Bourgault has become a bust. Surely the Oilers would LOVE to have Wallstedt as their starting goalie for the remainder of the McDavid and Draisaitl contracts rather than their current goaltending reality.

Related: Wallstedt blunder haunts the Oilers

All I’ve heard from Oilers fans all through the McDavid era is that draft picks don’t matter because they don’t help you win right now and that nothing matters three years down the road. Well, the “win now” decisions that were made early in the McDavid era matter a whole hell of a lot right now. They matter when you see young contributors that were in their hands like Holloway, Broberg, and Wallstedt doing what they’re doing now for other teams.

Did you know that the pick the Wild used to select Brock Faber was originally the Oilers’ pick? Holland traded that (2020 2nd round pick) and the 2021 second round pick for nine regular season games and four playoff games of Andreas Athanasiou at the 2020 trade deadline. There’s no guarantee that the Oilers would’ve taken Faber with that pick or that they would’ve taken Matthew Knies or J.J. Moser with the 2021 second round pick; but we are squarely in McDavid and Draisaitl’s primes and those second round picks would either have been spent differently or would be helping them now if a little bit of patience and future planning would’ve been used in 2020 instead of the “win now” philosophy.

I fully understand that teams that feel they’re in a championship window will spend picks for immediate help, but there’s something to be said for a little bit of restraint and calculated spending once in a while. There has to be more consideration than “the future doesn’t matter” and “draft picks won’t help us win now”. I’m fully convinced that the Oilers would’ve won at least one Stanley Cup by now if their ownership and management had been more patient during the early stages of the McDavid era.

That brings us to now. Those subscribing to the idea that this is the most important offseason in the history of the franchise are all screaming for the same things. 

They want Bruce Cassidy, the biggest and most experienced brand name coach available, to be the team’s next head coach. As soon as the 2023 Stanley Cup winner became available, Oilers fans were calling for him to be hired. 

Well, only six coaches in the history of the NHL have won Stanley Cups with multiple teams and none have done so since Scotty Bowman did it. Look at the Toronto Maple Leafs recently. Three of their last four head coaches came to them after having won a Stanley Cup, and look how that has turned out for them. Having won a Stanley Cup should not be the reason a team hires a coach.

Having said that, it shouldn’t be the reason they don’t hire someone either. I have shared opinions essentially stating that I wouldn’t hire a coach or a GM that has won a Stanley Cup because I want someone whose greatest success lies in front of them, not behind them. That’s the opposite extreme view. 

The coach needs to be the right person for the team. Is Cassidy that?

He has a reputation for having a shelf life due to his sometimes abrasive style. The panicked Oilers fans are thinking that’s perfect because they only need him for two years since McDavid will leave if they don’t win anyway. I hate that way of thinking to be honest. Maybe the Oilers need a bit of abrasion, friction, and honesty from their coach; but I wouldn’t intentionally hire someone thinking they would only be around for two years. Draisaitl will be around for six years after McDavid’s contract expires. Even if McDavid does leave, Draisaitl will want a contender built around him. It would be great to have a coach that the team can be a consistent contender with for many years to come. I’m not saying Cassidy can’t be that. If I was to hire Cassidy, I would hope it would be a long-term arrangement.

Cassidy has a reputation for being a great defensive coach. His Boston Bruins teams never ranked outside the top five in the league in expected five-on-five goals against in his six seasons at the helm according to Moneypuck. Cassidy’s Vegas Golden Knights weren’t as good defensively as those Bruins teams. They were never higher than thirteenth in the league in his first three seasons with Vegas. Them finishing second in that metric in 2025-26 feels like an outlier. 

As for Bruce Cassidy, sources indicate that was not part of the conversation and his status is unchanged as of this morning

Vegas is not inclined to give permission to Edmonton or LA. We will see about Toronto

— Elliotte Friedman (@FriedgeHNIC) May 19, 2026

Knoblauch’s Oilers teams in 2023-24 and 2024-25 finished in the top ten in that metric, which was better than Cassidy’s teams those seasons; but Knoblauch’s Oilers struggled to keep the puck out of their net in 2025-26. A lot of people would only look at last season’s stats and decide that Cassidy is a better defensive coach than Knoblauch. I contend that no coach would’ve made a big difference with the roster the Oilers had in 2025-26, and Cassidy’s Golden Knights finishing outside the top ten in three out of his four seasons there after being in the top five for six straight years with the Bruins tells me that the roster available to the coach has a lot to do with those results, but I digress.

Cassidy’s zone defence system beat the Oilers in the 2023 playoffs and forced Woodcroft to deploy his own zone defence the next season. However, Knoblauch and his zone defence beat Cassidy’s Golden Knights in five games in the 2025 playoffs. Does this sequence of events tell us that Cassidy would give the Oilers an upgrade defensively? I can’t say so conclusively.

I’m not saying that Cassidy is the wrong choice, but I’m also not fully convinced that he’s the right choice based on the evidence I have and the arguments that are being made in daily discourse online. I’d be more apt to go with an up and coming candidate like Misha Donskov than a coach like Cassidy or Peter Laviolette (who has a long history of mediocre results after winning the Stanley Cup in 2006).

The panic stricken “win now” and “Cup or bust” fans are also balking at the idea of trading for Sebastian Cossa, the other top goaltending prospect that went in the first round of the 2021 draft, because he will be an NHL rookie next season. The 23-year old had a .915 save percentage (6th in AHL) and a 2.33 GAA (5th in the AHL) this past season. Cossa now has three seasons of consistent results in the AHL. He has proven what he needs to prove down there. The Detroit Red Wings are higher on Trey Augustine than they are on Cossa, which is why Cossa is available. 

He could be the young long-term solution to the Oilers goaltending issue that Wallstedt should’ve been; but nope, that would go against the “win now” mentality of this offseason. It shows me that nobody has learned a damn thing from the last decade of watching the Oilers trip over their own feet in the pursuit of instant gratification during the McDavid era. My strategy wouldn’t be to get Cossa to be the guy right away though. The right decision is to trade for Cossa and to find a way to get rid of Tristan Jarry and bring in a different capable starter. Insulate Cossa the way they should’ve insulated Stuart Skinner when he was a rookie.

If you don’t think a rookie goalie can win a Stanley Cup, Cam Ward (who Oilers fans watched beat their team in 2006), Matt Murray, and Jordan Binnington all say hi. I get that you can’t plan on a rookie being the answer because a few others won Cups multiple years ago, but don’t rule anything out.

If the Oilers really want McDavid to sign a long-term extension with them sometime in the next two years, then there needs to be evidence that the team will be competitive long-term. That’s part of the reason why there was an emphasis on developing some younger players this past season.

If you think that evidence must be shown this summer, do you really think signing and/or trading for a bunch of players in their early thirties to overpriced deals with no-move clauses is what will show McDavid that there’s a path to long-term competitive viability in Edmonton? I certainly don’t. I would argue that would show McDavid that you think he’s going to leave and you’re not planning for a future with him, which is the ABSOLUTE WRONG MESSAGE TO SEND.

Careful, calculated decisions need to rule this offseason for the Oilers, not panic or desperation. There needs to be a focus on immediate success, but there absolutely must be a focus on life after the next two seasons if you want McDavid to be a part of that life. Players that are early in their primes or that are about to enter their primes should be the targets for Bowman and the Oilers this summer.

I personally don’t think that McDavid’s future with the Oilers is contingent upon whether or not they win a Stanley Cup next season. McDavid has been clear about his desire to win a Stanley Cup, but he has also been clear about his desire to win in Edmonton. I believe that his loyalty and the satisfaction that would come with having been a part of building a winner from the ground up in Edmonton are meaningful for McDavid. The only way that I could see him leaving is if Bowman screws things up so badly this summer that they miss the playoffs and are stuck with a collection of bad long-term contracts signed out of panic and desperation. I see some bad contracts getting signed or acquired this summer, but I don’t see any way the Oilers miss the playoffs.

I can’t be totally naive here either though. I’ll be devastated if McDavid decides to leave; but if he does, the reality is the Oilers will have Draisaitl under contract for six more years after McDavid’s contract expires and he will want a winner built around him for all of those years. The decisions made now will impact the teams in the middle of and at the end of Draisaitl’s contract. If we’ve learned anything from the first decade of the McDavid era, it should be that picks matter and the future matters. I’m not saying the Oilers shouldn’t add immediate help, but they need to do so more carefully and less aggressively than they have in the past.

The McDavid factor can’t be what dictates decision making this summer. Bowman and the Oilers need to make decisions that will keep the Oilers’ championship window open for the length of Draisaitl’s contract. The result of those moves is more likely to entice McDavid to stay rather than desperately trying to build a winning team with panic moves in a last ditch effort to keep McDavid right now.

I also fully believe that the Oilers have two summers to get this right. McDavid will be eligible to sign an extension next summer, and I understand not wanting to be in a position where the Oilers would be forced to let him walk away in free agency. However, he signed his latest extension last September after watching a summer of roster decisions unfold. If I was him, I would absolutely wait until after next summer to make a decision on my future. I would want as much information as possible before making that decision.

The cap is expected to spike to $113 million in 2027-28. They will be able to make more additions to bolster the roster in the summer of 2027 than they will be able to make this summer. If I was McDavid, I would wait to see what that roster looks like before making a decision one way or the other.

I know I’m in the minority on this, and that’s fine. I know the cries of “Cup or bust”, “win now”, and “all in” won’t be silenced. I know that ownership will dictate that management makes desperate panic moves this summer. I expect that. Good decisions are rarely fuelled by panic or made from positions of desperation though.