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The 4 Longest-Shot Underdogs Ever to Win the Stanley Cup

Hockey Player and NHL logo
Many American sports handicappers still live in Las Vegas out of habit. The phenomenon creates a nice loophole for bloggers like myself.

We tend to use “Vegas” as a shorthand for an entire community of oddsmakers. “What does Vegas think?” Obviously, Las Vegas is a city, not a person…it can’t “think” anything. The internet gives people the ability to handicap and set lines for sports betting sites from any location in the world. “The Vegas odds” and similar phrases are becoming mere figures of speech.

That’s why the Vegas Golden Knights were such a refreshing story in 2017-18. Here was a tale about an NHL expansion team from Las Vegas, who nearly caused a windfall for gamblers in Las Vegas by winning a Stanley Cup Finals series that alternated between Washington D.C. and Sin City.

Alas, the Capitals won the series, potentially helping to keep a number of small-time bookies in business. Preseason odds on the nascent franchise to win Lord Stanley’s Cup were in the (+50000) range. Nobody even expected Vegas to make the playoffs.

Back in the day before the Original Six began shaping the modern NHL landscape, the Cup was often held by barnstorming clubs who defended the trophy in challenge matches.

There were plenty of surprises and “major upsets” in that era. After all, nobody could go to YouTube and check out the competition.

But the NHL is still the “National Hockey League,” and the sport of pro hockey remains unpredictable. The Golden Knights couldn’t finish a miraculous Cup run in spring of 2018 – but plenty of heavy underdogs have turned the trick.

Here are just 4 long-shot sleepers who have prevailed with the grail.

2011-12 Los Angeles Kings

The L.A. Kings made history by becoming the first #8 conference seed to hoist the Stanley Cup since the NHL expanded to a 16-team playoff format in 1994.

After sneaking into the playoffs, the Kings rocked the Western Conference by ousting the top 3 regular-season finishers in succession. What’s more, the club only lost 2 games in the 3 series.

A lackluster offense had ranked 29th in scoring throughout an 82-game campaign that made skeptics out of loyal fans who had come to love the club during the Wayne Gretzky era. Even The Great One had failed to bring a Stanley Cup to SoCal, and it sure didn’t seem like 2012 would be the watershed.

Soon, though, the Kings’ work ethic began to pay off under coach Darryl Sutter. Conn Smythe winner Jonathan Quick was a brick wall in the postseason, allowing a GAA of 1.41 and posting 3 shutouts. Sutter had arrived in midseason, leading the Kings to an outstanding 12-4-3 record and giving the club momentum for the playoffs.

The Kings coasted to a convincing 6-1 win in Game 6 of the Stanley Cup Finals against the New Jersey Devils. Sutter would go on to win another title with L.A. in 2014.

1937-38 Chicago Blackhawks

Odds were long on the Chicago Blackhawks snagging a Cup victory away from the juggernaut Toronto Maple Leafs. Chicago had struggled to a 14-25-9 record during the regular season.

Of course, 80 years ago, the W-L-OTW-OTL format hadn’t yet been designed to make the average NHL record appear to be over .500. But the meager 14 wins were just part of the story. The Depression-era ‘Hawks were struggling with the puck, recording the least amount of goals in the NHL in ’37-‘38.

The Blackhawks righted the ship by ousting the Montreal Canadiens 2-1 and the New York Americans 2-1 before facing the Maple Leafs. Bookies still favored Toronto, a team led by Hall of Fame coach Conn Smythe. In a famous story, the Hawks were so banged-up between the posts that Toronto’s minor league goalie Alfie Moore was allowed to play for Chicago as a replacement.

It might have been a practical joke, since Toronto’s front office knew something that many in the Blackhawks organization didn’t – Moore was a lush. The loaner GK was found drunk shortly before the puck was scheduled to drop in Game 1.

But to everyone’s amazement the wobbly goaltender just needed a stiff shot of coffee. He “toasted” a 3-1 win over the shocked Maple Leafs.

Legend of Drunken Netminder wouldn’t be a double feature, as Smythe hilariously barred Moore from playing in the rest of the series. But formerly-injured goaltender Mike Karakas made an improbable return to lead the Hawks, who won the series in 5 games.

Chicago coach Bill Stewart became the first American skipper to hoist Lord Stanley’s grail.

1986 Montreal Canadiens

The Canadiens were not expected to amount to anything special going into the 1985-1986 season. The 1980s had been littered with mind-numbing early Montreal exits from the NHL playoffs.

Habs’ fans felt like potential golden years had been wasted, with much of the team’s core unit inching closer to retirement.

GM Serge Savard brilliantly navigated the NHL Draft, identifying future superstars like Claude Lemieux and goaltender Patrick Roy. A trade for former #1 draft pick Bobby Smith, formerly of the Minnesota North Stars, made a monumental impact for a club that qualified for the ’86 postseason as a steep underdog.

Gretzky and the Edmonton Oilers were favorites to win the Stanley Cup, but the Oilers lost in a major upset to the Calgary Flames. Meanwhile, the Canadians swept the Boston Bruins behind Patrick Roy’s brilliant .923 save percentage.

A magical overtime goal from Lemieux in Game 7 against the Hartford Whalers would lift the Habs to a 4-3 series win, followed by a 5-game romp over the New York Rangers in the conference finals.

After a feeble Game 1 performance against the red-hot Flames, the Canadiens exploded with 4 straight victories to capture the Stanley Cup.

Patrick Roy would go on to accumulate a more bling throughout a championship career, something that he hasn’t been shy to remind journalists and fellow players about.

1967 Toronto Maple Leafs

Imagine if the 2018-19 Red Devils of Manchester United had stuck with unpopular coach Jose Mourinho…and won the English Premier League anyway.

The 1967 Toronto Maple Leafs had an aging roster. But making these worse was what seemed like a total lack of cohesion with Hall of Fame head coach and GM Punch Imlach. Punch would part ways with the club in 1969, and some say his reign still hangs like a cloud over the franchise.

But in ’67 the skipper and the team managed to get along just long enough to claim an upset Stanley Cup win.

Goalie Johnny Bower had struggled to get through the regular season thanks to multiple injuries, but he somehow managed an outstanding postseason performance alongside veteran Terry Sawchuk. The duo led the Leafs to a shocking 4-2 series upset of the Chicago Blackhawks, a team that Las Vegas bookmakers expected to win Lord’s Stanley Cup.

The Leafs then faced a Montreal squad which had gone 15 straight games without a loss and had swept Toronto in the previous year’s playoffs. The underdogs would over-achieve once again, besting Montreal 4-2 behind crafty goal-scorer Jim Pappin.

Toronto had slayed a 2-headed dragon to win the most special prize in hockey. Did Punch curse the team when he left it 2 years later? The Maple Leafs have yet to win another league title.