The fatal flaws of 6 Canadian Cup losers and why they don’t apply to the 2024 Oilers

I think the Edmonton Oilers are going to do it.

I think they’re winning the Stanley Cup this year, for all the reasons I laid out in that debate with Sean Gentille last week. I’d obviously feel better about that prediction if they’d been able to win Game 1, but they dominated enough stretches in the loss that I still say they do it. And no, that has nothing to do with them being Canada’s team, because that’s not a thing. I just think this is their year.

But as much as we might want to hand-wave it away, the 31-year Canadian drought does hang over this series, especially with six of the country’s teams having made the Final since 1993 only to lose. So today, I’m going to try to reassure myself that I’ve made the right pick by looking back at those six Canadian near-misses. We’re going to identify the Canadian Final loser’s fatal flaw, and then make sure it doesn’t apply to this year’s Oilers.

We’ll do this in order of difficulty, starting with the easiest team to ignore and ending with the comparisons that worry me a bit. And that means we begin with our most recent loser …

The team: After an uninspiring regular season that saw them lose eight more games than they won and fire their coach on the way to a fourth-place finish in the Canadian Division, the Canadiens stunned us all with an unexpected playoff run all the way to the Final.

The Final: With a ton of momentum and the hockey world starting to believe in Carey Price playoff magic, the Habs ran into the defending champion Tampa Bay Lightning in the Final.

The result: The magic ran out against the Lightning, as Montreal dropped the series in five games.

The fatal flaw: They weren’t good.

OK, that’s a little harsh. The 2021 Habs had their strengths, led by veterans Price and Shea Weber. And they’d beaten some decent teams to get to the Final, including a Vegas Golden Knights team that had finished tied for first in the league. As surprise finalists go, these weren’t exactly the 1991 North Stars.

But the whole appeal of this run is how unexpected it was, as the Canadiens looked to become one of the greatest Cinderella stories of all time. You can’t weave that narrative without accepting that it only works when the team is punching above their weight class. And outside of a few weeks at exactly the right time, this Montreal team just wasn’t all that good.

Why it doesn’t apply to this year’s Oilers: They’re actually good.

That was easy. OK, enough with the warmup, let’s up the difficulty a bit.

The team: The Flames rode Jarome Iginla and Miikka Kiprusoff and not much else to a 94-point season, then pulled off a string of upsets to advance to the Final.

The Final: They faced the Lightning in what ended up being a sneaky good series, one memorably highlighted by Iginla dropping the gloves with Vincent Lecavalier. The Flames led the series at three separate points and had a chance to win the Cup on home ice in Game 6.

The result: It was in.

The fatal flaw: Other than being robbed by the replay booth, the Flames’ biggest problem was that they just couldn’t score. They had ranked third in goals against that year, but just 19th in goals for, and Iginla was the only player on the roster who even cracked 50 points. The team’s fifth-leading scorer was defensive defenseman Jordan Leopold. And during a Final where even one more goal at the right time would have tilted the result, tough guy Chris Simon was tied for second in team scoring. With three points.

Why it doesn’t apply to this year’s Oilers: I feel like they’re going to be OK when it comes to offense. The Flames managed to score just 14 times in the seven-game Final; there are nights when it feels like the Oilers are a threat to get that many in a game.

Queue up the Spiderman pointing meme for our next entry …

2006 Edmonton Oilers

The team: Maybe the best Cinderella story of the Cap era, the Oilers went from forgotten eight-seed to within a game of a championship, based on a motley crew of fun characters and the goaltending of deadline addition Dwayne Roloson.

The Final: The Oilers lost a tough one in the opener, blowing a 3-0 lead and giving up the winner on a mess of a play.

They trailed the series 3-1 before fighting back to force a Game 7 in Carolina.

The result: They just ran out of gas in that deciding game, as Cam Ward held them to just one goal in a heartbreaking 3-1 loss.

The fatal flaw: Their goalie got hurt in Game 1.

I’ll admit we’re oversimplifying here, and probably making a few Carolina fans furious in the process. The Hurricanes were an excellent team that year, maybe not underrated in the moment but certainly in hindsight. (They’d had 112 points, tied for third in the league, and had the third-best offense by goals scored.) Ward’s emergence was the Final piece, and the Hurricanes were worthy winners.

But all that said, I still think the Oilers win if Roloson is healthy. That’s Ty Conklin handing the Game 1 winner to Rod Brind’Amour up above, and it was the last we’d see of him in the series. Jussi Markkanen took over, and he was decent enough that you could argue he didn’t cost Edmonton a game — he got shelled in Game 2, but the Oilers were shut out, and he only gave up a combined four goals in the other two losses. Still, if a healthy Roloson wins Game 1, the whole series changes. We’ll never know how it plays out, but Edmonton lost its second-best player early in the series, and that has to have an impact.

Why it doesn’t apply to this year’s Oilers: Stuart Skinner made it out of Game 1 unscathed, so that’s progress. More importantly, this Edmonton team does not rely on its goaltending to be its best player. Skinner doesn’t have to be great to win this series. He just has to be good enough. That’s a much lower bar than the one Roloson didn’t get a chance to clear in 2006.

The team: This was the peak of the Senators’ contention era, as they finished second in 2005-06 and followed that up with 105 points and a 12-3 playoff run that made quick work of the Eastern Conference. This was the team that featured the Pizza Line, with Jason Spezza centering Daniel Alfredsson and 50-goal man Dany Heatley.

The Final: Ottawa seemed to match up reasonably well with the Anaheim Ducks team built around three Hall of Famers in Teemu Selanne, Chris Pronger and Scott Niedermayer, plus youngsters Ryan Getzlaf and Corey Perry.

The result: The Senators picked a bad time to unravel, with their most memorable moments being Chris Phillips scoring into his own net and Alfredsson shooting a puck at Niedermayer.

The fatal flaw: Aside from being in their own heads, the Senators ran into a team featuring two of the best defensemen of their era. With one of Pronger or Niedermayer on the ice for virtually the entire series, the Senators just couldn’t get their second-ranked offense going. One skater can’t singlehandedly win his team the Cup, as every fan knows. But it turns out two skaters can come pretty close.

Why it doesn’t apply to this year’s Oilers: The Florida Panthers’ blue line is good, so we’re getting into some concerning territory here. But the Florida defense is more about a team buy-in than elite talent on the back end, so the comparison doesn’t really hold. Gustav Forsling is having a fantastic season as a breakout story, and guys like Aaron Ekblad and Brandon Montour are very good. But there’s no Pronger lurking here, and that means the Oilers’ offense will get on track eventually.

(Probably. We’ll get to that in a minute. For now, we’ve got two losses left to go, and they’re both from the same team.)

The team: This was back in an innocent time when the Canadian Cup drought wasn’t even a thing, as Montreal had just won the country’s eighth championship in 10 years. Along came a scrappy band of Canucks underdogs the whole country could get behind — not out of a sense of duty, but just because they were so easy to root for.

The Final: The matchup with the 1994 New York Rangers felt more like a coronation than a contest, as just about everyone had apparently decided Mark Messier’s quest to end the 54-year New York drought was destiny. The Canucks missed that memo, giving the Rangers everything they could handle while coming back from down 3-1 in the series to force a Game 7.

The result: Nathan LaFayette hit the crossbar, and the Canucks quest fell just one goal short.

The fatal flaw: They were playing the best team in the league.

The Rangers had won the Presidents’ Trophy and had the MVP and a 50-goal scorer, plus great goaltending and a blue line featuring youngsters Brian Leetch and Sergei Zubov. They’d rolled through the first two rounds, then backed up Messier’s infamous guarantee to beat the New Jersey Devils in the conference final. The Canucks felt like massive underdogs heading into the Final, and even though they exceeded all expectations, it still wasn’t enough because there was just no margin for error.

Why it doesn’t apply to this year’s Oilers: The massive underdog part certainly doesn’t, although the odds shifted decisively toward the Panthers in the days before Game 1. The question is just how good Florida really is — there’s a good case to be made that the Panthers are the best team in the league, even without a Presidents’ Trophy or an MVP-caliber start.

2011 Vancouver Canucks

The team: With apologies to the 2007 Senators, you could make the case that the 2011 Canucks were the only Canadian team to go into the Final as favorites. And rightly so, as they’d just won the first of two straight Presidents’ Trophies. With the scoring champion, the previous year’s MVP, that year’s Selke winner, a Hall of Fame goaltender and all the right supporting pieces, they looked like the prototype of a modern Cup team.

The Final: The Canucks faced the Boston Bruins, a 103-point team featuring Patrice Bergeron and Zdeno Chara. They were tough to score on, had a balanced offense and had Tim Thomas in goal. It was a tough matchup, sure, but a winnable one, especially after the Canucks took a 2-0 series lead.

The result: I’m not sure Canucks fans are ready to talk about it.

Basically, they fell apart. Whether you want to say that was mentally or just on the ice is up to you, but it was ugly. They lost Games 3 and 4 in Boston by a combined score of 12-1. They earned a 1-0 win on home ice in Game 5, but no-showed Game 6, falling behind 4-0 after one period on the way to a 5-2 loss. That set up a winner-take-all Game 7 back in Vancouver, and … it didn’t go great.

The fatal flaw: They got goalied.

It wasn’t just that. The Bruins were a good team, and nobody’s saying they didn’t deserve their Cup. The goalie is a part of the team, so having the best one isn’t a knock.

But man, did the Bruins ever have the best goalie here. Thomas was absolutely unreal all year long, winning his second Vezina, and he upped his game in the Final to the tune of a ridiculous .967 save percentage. From the moment they took a 2-0 series lead, the Canucks managed just four goals in five games. And it’s not like they couldn’t generate chances; they had 37 shots in that Game 7 shutout. They just couldn’t beat Thomas, and that meant nothing else mattered.

Why it doesn’t apply to this year’s Oilers: This is the one that scares you if you’re picking Edmonton.

Thomas was a 36-year-old two-time Vezina winner. The Oilers are facing Sergei Bobrovsky, a 35-year-old two-time Vezina winner. And on Saturday night, it’s fair to say he looked especially Thomas-esque. That has to be terrifying for Oilers fans.

As the 2011 Canucks proved, sometimes a goalie really can make all the difference. That’s not to say the Bruins weren’t worthy, or that the Canucks didn’t have some self-inflicted wounds. But none of that really mattered once Thomas decided he just wasn’t going to allow any goals. If Bobrovsky is going to pull the same trick, this series is already decided.

So does this one apply to the Oilers? I’m not sure. It might. If McDavid and friends want to reassure us on this one, tonight would be a good time to start.

(Photos of Dwayne Roloson and Stuart Skinner: Dave Sandford, Joel Auerbach / Getty Images)