A brief history of underdog runs ending badly in the final (and whether that should worry Habs fans)

While it didn’t end the way they’d hoped, the Montreal Canadiens just pulled off one of the great underdog runs in NHL history. They went from finishing 18th and going into the playoffs as an afterthought all the way to the final, and finished just four wins short of doing the unthinkable. It was pretty amazing.

It also wasn’t especially rare in the modern era, and that’s where this gets a bit tricky if you’re a Habs fan looking toward the future. For reasons I’m not quite clear on, the NHL tends to serve up one of these underdog runs to the Stanley Cup final every few years, including some featuring teams that were bigger longshots than the Canadiens. But they all seem to end the same way – with the underdog losing in the final, sometimes decisively. And it’s the part that comes next that should worry Montreal fans: A lot of these teams never came close to contending again.

History can teach us some things, but it doesn’t necessarily predict the future. So today, let’s look back on ten underdog teams from modern NHL history that had a similar run to what the Canadiens just pulled off, and how the rest of their story unfolded once the final was over. We’ll look for any similarities or key differences when it comes to this year’s Canadiens.

I’ve picked ten of the biggest underdog runs from the last 30 years. We could probably argue over some of these, or try to cram in a couple more. I didn’t include a few teams you might be expecting to see, like the 2002 Hurricanes (who won their division and had home ice through the first three rounds), the 2012 Devils (who had 102 points despite being the six-seed), the 2016 Sharks (who had a respectable 98 points and had been to two recent conference finals), or the 2018 Golden Knights (who were certainly shocking as an expansion team, but had a dominant 109-point regular season).

Maybe we’ll learn something. Or maybe we’ll just remembers some underdogs. Either way, we’ll start 30 years ago and work our way forward, meaning we get to kick things off with what might still stand as the most shocking underdog run in modern NHL history.

1991 Minnesota North Stars

The underdog: The North Stars were a legitimately bad team, finishing the year with just 68 points to finish 16th in a league that only had 21 teams. And to make matters worse, this was the one year that the Norris Division was actually good, with Chicago and St. Louis finishing as the NHL’s top two teams to set up an inevitable battle for the ages we all assumed we’d get in round two.

The unexpected run: The North Stars shocked the Blackhawks in six and then did it again against the Blues. For their trouble, they earned a conference final meeting with the defending champions, an Oilers team that hadn’t been very good during the season but still had plenty of remnants of the dynasty years, including Mark Messier and Grant Fuhr. Minnesota beat them in five.

The final: The North Stars faced the powerhouse Penguins in the final, and actually led that series 2-1 after three games. But Mario and friends were too much, and Minnesota’s miracle run fell two wins shorts of the most unlikely championship in NHL history.

But then: The North Stars didn’t get any sort of boost from their run, finishing 1991-92 with just 70 points. Worse, they never won another playoff round in Minnesota, moving to Dallas in 1993.

Why they might worry Habs fans: A huge factor in the downfall of the North Stars was who they lost in the expansion process that welcomed a new team to a West Coast market.

Why they might not: Who they lost in expansion was “literally half the roster”. Yeah, it gets complicated, but let’s just say I don’t see the Canadiens having the same problem with Seattle.

1993 Los Angeles Kings

The underdog: Los Angeles finished the season with just 88 points in a conference where five teams had 97 or more. They also had a franchise player who was injured for half the season (Wayne Gretzky) and a new and largely unknown coach with cool hair (Barry Melrose). Hey wait a second…

The unexpected run: The Kings upset the Flames and Canucks, both in six games, to take the Smythe crown. Then they pulled off a memorable seven-game win over the Maple Leafs that you may have heard about.

The final: The Kings went into the Forum and took Game 1 over the favored Habs, and were on the verge of taking a 2-0 series lead when Marty McSorley taught us all about the NHL’s illegal stick rules. Montreal swept the rest of the series, winning in five.

But then: It all collapsed shockingly quickly. Melrose only lasted one more full season, Gretzky was traded in 1996, and L.A. wouldn’t make the playoffs again for five years or win so much as a round until 2001.

Why they might worry Habs fans: There are a lot of similarities here, including the Melrose/Dominique Ducharme comparison and the injured superstar. There’s even the all-Canada angle; Montreal played in the North Division, while the Kings only faced Canadian teams on their run.

Why they might not: Unlike the 2021 Habs, this miracle run actually ended in a Montreal win. (Sorry, sorry, I’m trying to delete it.)

1994 Vancouver Canucks

The underdog: The Canucks finished the season with 85 points, making them the seven-seed under the league’s new conference-based playoff format. Nobody gave them much of a chance, especially when they fell behind 3-1 in the opening series.

The unexpected run: It took three overtime games, but the Canucks clawed back win that opening round against Calgary, finishing it with one of greatest OT goals ever. They went on to beat the Stars and Leafs, both in five games.

The final: The Canucks faced the Presidents’ Trophy winning Rangers, a 112-point powerhouse riding high off of Mark Messier’s guarantee and a memorable conference final win over the Devils. The Canucks fell behind 3-1, then fought back to delay the coronation before finally dropping a heart-breaking Game 7.

But then: The Canucks did win a round in 1995, but it would be the last one they’d win until 2003, including a four-year span with no playoff appearances at all.

Why they might worry Habs fans: I mean, they fell behind 3-1 to a Canadian rival in round one, came back to win that series based on overtime magic, won the next two rounds in just ten total games, then faced the best team in the league.

Why they might not: The Canadiens aren’t dumb enough to sign Steven Stamkos as a free agent in three years and watch him wreck the team from the inside… are they?

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