Typically, in the Sunday Scramble, I take a ripped-from-the-headlines approach to the hot topics across the hockey world. But this week I’ve been thinking about history and how it applies to this version of the Edmonton Oilers.

Can we really expect this team to start well? They never seem to do so anyway, but what about the context of back-to-back trips to the Stanley Cup Final? How does that go for teams?

I was thinking about this while watching the Oilers get shelled by the Avalanche earlier this month, and wondered out loud if we were expecting too much. This led me down the rabbit hole of looking at teams in similar positions. I wanted to calibrate my expectations compared to great teams of the past.

Ken Dryden’s book The Game describes a problem he referred to as the “strange monotony of success at the highest level.”

The chalice-winning success of those 1970s Montréal Canadiens created an environment where the joy of victories became ever more fleeting, and every loss seemed like a failure.

Now, many things have changed in the game since the 1970s, stylistically, expansion, parity, etc, that make Stanley Cups more difficult to win in the Year of Our Lord 2025.

And this edition of the Edmonton Oilers seems bitten by this same bug of monotony through the quarter point, where the trials and tribulations of the early season don’t hold your attention, knowing greater challenges lie ahead. It’s even more frustrating for these players because they’ve come so close.

After back-to-back Stanley Cup Final losses, how do they rev up emotionally so they can come together as a hockey team? They can’t win the Stanley Cup next week, month, or even six months — they can only dig themselves into a hole that will make it harder later.

There’s more to it

I’m not saying this is the team’s only issue — far from it.

Past the usual sluggish starts, there are systematic and personnel problems that are glaring, which make this 2025-26 start a real cause of concern. Poor, poor goaltending, blinding defensive gaffes, and a shockingly uneventful offensive side of their game have Oil Country uneasy.

It’s not just the fatigue, either. It’s the collective trauma and frustration of seeing the finish line and falling short.

In the second part of this series, we will look deeper at the nine teams since 1990 that were in this same spot.

Since Florida (and just before them Tampa Bay) have just achieved three straight Wales Championship trophies, you could be misled into thinking that this is common. That winning a Stanley Cup in your third straight trip wasn’t such a big deal.

It was a very big deal, in fact. Florida is the only team in the modern NHL to win the Stanley Cup in their third consecutive trip to the Final. They were the first to do so since the 1984-85 Oilers, who similarly lost on their first trip, then won back-to-back.

Even in the days of a six-team, 12-team, 21-team, or even 24-team NHL, it was very difficult to return a third straight time.

Florida is the outlier.

Just so we know

A couple of other historical notes…

Every team in the past 30 years in the same position the Oilers are in had won a Cup in their previous two attempts.
Most of the time, they got bounced in the second round or sooner, but each team made the playoffs.
The last time a team lost back-to-back Stanley Cup Finals and then won the following year was the 1955-56 Montréal Canadiens.

Historically, these Oilers feel like the 1978-79 Boston Bruins, who had lost twice in a row to Montréal, and would again, a third time in the semi-finals. That was the infamous Too Many Men on the Ice Game 7 call that became Don Cherry’s most famous moment (outside of broadcasting). But that team didn’t have Lafleur, and Edmonton has theirs in McDavid.

The St. Louis Blues of 1969-70 were the last team to make the SCF in their third straight try after losing the past two seasons (but that had a lot to do with expansion and division alignment). They were soundly swept by the Boston Bruins and posterized in the most famous hockey picture of all time, Bobby Orr flying through the air while scoring the clinching goal.

But as I say, this was a long time ago, and much has changed. How have teams in more recent memory fared?

Let’s stress this first: this isn’t meant to be doom porn. This is an exercise in understanding how other championship-level teams dealt with the same slings and arrows, and perhaps help us understand how hard it all is to achieve – even after you’ve been there.

It’s not about saying punt the season because of long-gone history. This edition of the Edmonton Oilers could win the Stanley Cup. It’s within the range of outcomes with the talent they have on their team. A little bit of understanding goes a long way.

Let’s take a look at one team on the list before we go, perhaps the best one in the lot…

1992-93 Pittsburgh Penguins (lost second round)

EDM record after 20 games: 9-7-4
PIT record after 20 games: 13-4-3
Finish: 56-21-7, 119 points, first in East (Presidents’ Trophy)

No team was more equipped in the past 30 years to win a three-peat. This team was a wagon: Mario Lemieux, Jaromir Jagr, Kevin Stevens, Rick Tocchet, Larry Murphy, Ron Francis, and Tom Barrasso.

Smarter and more alive people than I have said the 1992-93 Penguins were the best Pittsburgh team out of the bunch. It’s the only team on this list that won the Presidents’ Trophy, and PIT went unbeaten in their first ten games. Six players reached the 85-point plateau, and eight reached the 22-goal plateau. They scored a franchise high 367 goals and seemed unbeatable.

Mario Lemieux had 160 points in 60 games after literally coming back from cancer, and upon his return, Pittsburgh went on an NHL record 17-game winning streak, which ended on the last game of the year in a tie. The only consequential loss from the team was the retirement of Bryan Trottier, who stepped in beside the bench as an assistant for the legendary Scotty Bowman.

The New York Islanders’ seven-game upset in the Patrick Division Final is one of the biggest in NHL history. In a series of hooking, holding, and Glenn Healy standing on his head, David Volek was the Game 7 OT hero as the Isles played like their lives depended on it.

The upset isn’t so remembered because they would be soundly beaten by the Canadiens in five games, but this series was a brutal battle, a true Classic Series on NHL Network. It’s still a shock to Penguins fans of that age.

In Part 2, we’ll take a similar view at each team in this same position, comparing the start and peaking at their finish…

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There’s more to it

Just so we know

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