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NHL worst gut-punch losses series: Chicago Blackhawks, Winnipeg Jets and Pittsburgh Penguins.

By The SI Staff
August 17, 2015

Every fan must endure bitter defeat from time to time, but when it comes to choosing the most painful loss ever suffered by a team there are many factors to consider: the expectations, the opponent, the stakes. Blowout losses hurt, but it’s the close ones—the ones that got away, or the ones that were decided by fickle fate—that are often the most memorable.

This series revisits each NHL franchise’s most bitter loss. Here is Part 9:

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Chicago Blackhawks: May 18, 1971; Eastern Conference Semifinals, Game 5—Canadiens 3, Blackhawks 2 

While the Blackhawks’ loss to the Kings in their epic Game 7 of the 2014 Western Conference Finals stands out as a tough one, Chicago’s 5–4 overtime defeat at home was sandwiched by three championships in six seasons, so it’s hard to pick it as the absolute worst gut-punch in the team’s long, storied history. It’s more likely that one was delivered back in 1971 when the Hawks and Canadiens met in an “Original Six” showdown for the Cup. Chicago was making its first appearance in the Final since 1965 and seeking its first championship since ’61. The Canadiens were on a run of six Cups in nine years.

NHL fan misery rankings 2015
 within one.

According to the Chicago Tribune game story, Canadiens captain Jean Béliveau said, “If we hadn't gotten this one, we would have been dead.”

Though that goal gave life to Montreal, there were plenty of missed opportunities by the Blackhawks. In the second period, Bobby Hull hit the crossbar and Jim Pappin missed a chance at the side of the net. Chicago just couldn’t put the Canadiens away.

Then with 1:20 left in the period, Lemaire sent a loose puck that caromed off the base of the net to Canadiens forward Henri Richard, who was set up in front of Esposito. Richard quickly tied the game at 2–2. The tide had turned in the Canadiens’ favor, and at 2:34 of the third period it was Richard who struck again. The Hall of Fame forward beat a diving Keith Magnuson to give the Canadiens the 3-2 lead. The tally ended up being the game-winning goal.

Chicago had quite a few chances in the third period, but the Hawks were stymied by young goaltender Ken Dryden, who’d had all of six games worth of NHL experience when the playoffs began. During one play Pappin was alone on the right side of Montreal’s net with a clear shot on goal but he couldn’t elevate the puck over Dryden’s right leg. The Hawks pulled Esposito with less than a minute remaining, but even with six attackers, they couldn’t get much pressure on Dryden. The Canadiens held on and became only the second road team in NHL history to win a Game 7 of the Stanley Cup Final. The Cup was Montreal’s 16th, and the rookie Dryden won the Conn Smythe Trophy as the MVP of the playoffs. The two teams would meet again in the Final two years later, but the Hawks fared no better, losing in six games. The squandered opportunity of ’71 would haunt the franchise until 2010 when Chicago finally won the Cup again. — Sarah Barshop

Winnipeg Jets: April 25, 2013—Canadiens 4, Jets 2

When it comes to the Jets, there are very few choices other than regular season games. The franchise (the former Atlanta Thrashers) has appeared in only eight playoff games during its history—all were losses—and none stand out as particularly traumatizing because the team just wasn’t very good and only the most pop-eyed optimist would have anticipated a victory. In 2007, the Thrashers’ postseason debut, they fell behind the Rangers early in the first period of Game 1 and didn’t hold a lead until Game 4 en route to being swept. Their second postseason appearance, after their relocation to Winnipeg, came in the spring of 2015 when the renamed Jets were swept by the Ducks. But Winnipeg's passionate, exuberant fans took the team’s swift exit as well as could be expected. They gave their team a standing ovation when the series was all over. There were no tears, no crinkly faces of utter despair. Honestly, they just seemed happy to be there.

Biggest gut-punch loss for every NFC franchise in the Super Bowl era
Biggest gut-punch loss for every AFC franchise in the Super Bowl era

To make matters even worse for the Penguins and their fans, the game left another legacy. Early in the game, Pittsburgh lost winger Kevin Stevens to a catastrophic hit in the face from defenseman Rich Pilon. By many measures, the two-time-50-goal scorer just wasn’t the same after. And neither were the Penguins, who would not win another Cup until after Sidney Crosby replaced Lemieux as the team’s superstar leader. — Sarah Kwak

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