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.
The Blackhawks, who had home ice advantage in the series, jumped out to a 2-0 series lead, but the home team held serve and both squads found themselves in Game 7 at Chicago Stadium. Thanks to second period goals by Dennis Hull and Danny O’Shea, the Blackhawks took a 2-0 lead. But with just over five minutes remaining in the period, Canadiens forward Jacques Lemaire fired a shot from center ice that seemed to surprise everyone including Blackhawks goalie Tony Esposito. The puck flew over the netminder’s right shoulder and pulled Montreal within one.
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.
Which brings us to a loss that did wrench hearts in Winnipeg. After losing the Original Jets to Phoenix in 1996, the Canadian city had yearned for an NHL team to return. In 2011, Winnipeggers finally got their wish. So what if the new team in Manitoba had to play in the Southeast Division with ridiculous travel demands? But in 2012-13, with the regular season shortened to 48 games by the lockout, the schedule was a bit kinder, and though the Jets (24-21-3) were far from stellar, they remained in the playoff mix during the final weeks of the season. In April, they won five-straight games to put themselves into a berth with only four games left, but a 1-1-1 skid in the final week, including a costly loss to Capitals, set up their last game, which was played at home against Montreal in front of a sell-out crowd of 15,004. When the puck dropped, the Jets’ postseason hopes were still alive, albeit barely. They needed the Rangers or Senators to falter in their season finales, but neither did. By the end of the second period, the out-of-town scores were in and the Jets and their fans knew their season was over.
What really hurt was the third period. The Jets had built a 2-1 lead going into it, but the news of their elimination drained all energy in the MTS Centre. A team known for fighting hard to the bitter end went out with a whimper as Montreal scored three unanswered goals in the last frame, a final kick when Winnipeg was already down.
“I’m going to have a hard time drawing on any positives, when you’re going home and watching the important hockey being played from your couch again,” said winger Blake Wheeler. “That’s going to be tough to swallow.” — Sarah Kwak
• Pittsburgh Penguins: May 14, 1993; Patrick Division Finals, Game 7—Islanders 4, Penguins 3 (OT)
In the spring of 1993, Mario Lemieux’s Penguins were a powerhouse, a bona fide dynasty in the making. After capturing consecutive Stanley Cups in 1991 and ’92, Pittsburgh entered the ’93 postseason as the most fearsome team in the NHL with a league-high 119 points and four players who’d scored more than 100 points that season. Amazingly, Jaromir Jagr wasn’t even one of them (he finished with 94). This was also the year that Lemieux was diagnosed with Hodgkin’s lymphoma and sat out two months while undergoing radiation treatment. When he returned in March, he was trailing the league scoring leader by 12 points; by season’s end, he'd won the scoring title by 12.
With Lemieux back on the ice, the Penguins finished the season with a record 17-0-1 run, outscoring opponents by an almost 2-to-1 margin. Against the Devils in the first round, Pittsburgh quickly raced out to a 3-0 series lead, extending their postseason win streak to 14. Though New Jersey managed to win Game 4, the Devils were overmatched. On paper, so did the Penguins’ next opponents, the Islanders. But the Isles held an infamous place in Pittsburgh sports lore. In 1975, they became the second team in NHL history to win a series after trailing three games to none, and they did it against the Pens. In 1992-93, the Isles were the only team that had managed to be the dominant Penguins three times. And there was at least one ominous sign: Lemieux’s back was bothering him, he had to spend time in traction, and his play was affected.
After taking a three games to two lead the Penguins, feeling the pressure of being heavy favorites against a loosey-goosey underdog, were unable to bury their pesky foes and lost Game 6 on Long Island, 7–5. What transpired next in Pittsburgh still haunts Pens fans. Despite overwhelming the Islanders and outshooting them 26-11 through the first two periods, the Pens found themselves in a 3-1 hole with just five minutes left in the game. Pittsburgh center Ron Francis cut the lead in half, and then with an extra attacker, the Pens tied the game on a goal by Rick Tocchet with a minute left. Going into overtime, their confidence was high. But at 5:16 of the extra session, the Islanders took advantage of a 3-on-1 break and little-used winger David Volek beat Pittsburgh goalie Tom Barrasso for the second time that night, reducing the Civic Center to stunned silence. The headline in The New York Times the next day read: “Improbable. Impossible. Incredible. Islanders.”
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