SI Staff
Thursday August 13th, 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 8:

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Washington Capitals: May 8, 2015; Eastern Conference Semifinals, Game 5—Rangers 2, Capitals 1 (OT)

Pick the worst defeat in Capitals history? One? We’re talking about the franchise that has made gut-punch losses an art form. As a Caps fan I could write a book.

We could go with the obvious, easy choice: the nightmare created by the Islanders and Pat LaFontaine on April 18, 1987 when they beat the Caps 3–2 in four overtimes to complete a comeback from a 3-1 series deficit. A game that started at 7:30 p.m. on Easter eve ended just after 2 a.m. on Easter Sunday. That one helped set a tone of the Caps usually (but not always) falling short in Game 7s and often blowing 3-1 series leads.

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In the interest of saving space, we’ll skip over many of these types of games and get into more recent history. In 2009, the Caps lost three in a row in the second round of the playoffs against the Penguins, then actually toughened up and won Game 6 in OT. They followed that up by getting blown out 6–2 in Game 7. But that’s not my pick. In 2010, the Caps won the Presidents’ Trophy by amassing 121 regular-season points and earning the top seed in the playoffs. They then blew a 3-1 series lead (yep, again) against eighth-seeded Montreal, losing 2–1 at home in Game 7. They scored 17 goals in their three victories, then one in each of the three losses to close it. But that’s not my pick.

OK, how about 2013 when the Caps took a 3-2 series edge on the Rangers in the first round of the playoffs with a thrilling overtime victory in Game 5. Little did anyone know that Mike Ribeiro’s winning goal in that game would be Washington’s last of the season. They lost 1–0 on the road in Game 6 and then laid a massive Capitals egg in Game 7 at home with a 5–0 defeat.

But that isn’t my pick, either. Nope, the biggest gut-punch loss in Capitals’ history actually occurred this past season and it wasn’t even an elimination game. It was their 2-1 overtime loss in Game 5 against the Rangers on May 8 in the second round. Granted, that seems like a very odd choice for a franchise that has folded up its tent in big-time ways in many big-time games. The loss didn’t end the Caps’ season. In fact, they still had a 3-2 series lead (yes indeed, they were up 3-1 once again) and two more chances to send the Rangers into the off-season. So allow us to explain. That game proved that no matter how many positive changes this franchise makes, it can’t outrun its karma.

Against an excellent Rangers team, the Caps had earned their 3-1 advantage. Their edge was slight but legitimate. For much of Game 5 at New York’s Madison Square Garden, they were in control in another tense, low-scoring affair. After Curtis Glencross scored at 10:54 of the third period it seemed that maybe, just maybe, this team would get past the second round for the first time since 1998. Braden Holtby was stellar in goal again. The Caps were in control.

Then Chris Kreider scored for the Rangers with 1:41 to play and shoulders slumped all across Caps Nation. You knew, just knew, where this was headed. The Caps would go on to lose in overtime (they did). They would find a way to lose Game 6 at home (they did). And they would ultimately break their hearts of their fans with another Game 7 loss after having a 3-1 series lead.

And they did.

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Granted, this was a different Game 7. They weren’t blown out, weren’t embarrassed. It was as good a game as there was in the 2015 playoffs, with New York finally prevailing 2–1 at MSG on a Derek Stepan goal 11:24 into OT. No doubt the Rangers and their fans heaved a huge sigh to have the formidable Caps out of the way. But you know what an encouraging loss and an embarrassing loss have in common? They’re still losses.

That’s kind of the whole point of why that loss to the Rangers hurt much more than many of the others mentioned above. This was not the same ol' Caps. First-year general manager Brian MacLellan and first-year coach Barry Trotz did an excellent job remaking this team’s roster, approach and attitude. There was a different vibe to this team all season. The case in point during the regular season came on New Year’s Day when Washington ground out a 3–2 victory over the Chicago Blackhawks in the Winter Classic in D.C. The Caps didn’t play well for much of the game but they found a way to hang in until they found a way to win. Maybe, just maybe, this would be a different year.

In the first round of the playoffs, Washington beat the Islanders in Game 7 to set up the clash with the Rangers. For four games of that series and most of a fifth, Capitals fans were giddy. Things were definitely changing.

Then, 101 seconds away from closing out the series, Kreider scored and reality delivered that hard punch right smack in the gut. — Mike Harris

• Buffalo Sabres: June 19, 1999; Stanley Cup Final, Game 6—Stars 2, Sabres 1 (3 OT)

With all due respect to Washington, D.C. and Capitals fans, Buffalo has well-deserved reputation as hockey’s heartbreak hotel. During their 45 years of existence the Sabres have boasted some pretty talented teams and legendary players (Dominik Hasek, Gilbert Perreault, Rick Martin, René Robert), but getting a shot at the Stanley Cup has proved to be frustratingly elusive. They have had only two: their six-game loss to the Flyers in the 1975 Final and their six-game defeat by the Stars thanks to Brett Hull’s infamous foot-in-the crease play in 1999. That one was the hardest punch of all.

Still, 16 years later, the words “No goal” ruffle the feathers of Sabres fans, who suffered the grave injustice of the Stars winning the Cup in Buffalo on a bitterly disputed goal. After splitting the first four games, the Sabres were shut out, 2–0, in Dallas and returned home facing elimination and determined to stay alive. In Game 6 Hasek allowed a puck to bounce off his pad and into his net in the first period, but the Sabres tied it at 1–1 in the second when Stu Barnes’s shot went off a Dallas defenseman and past Stars goalie Ed Belfour. From there, the game was a total goaltending duel.

One overtime came and went. Then another. After two extra frames, the score remained tied, 1-1, thanks to the remarkable performances of Hasek and Belfour. But late in the third OT, Dallas winger Brett Hull, in close on Hasek, played a rebound, kicking it to his stick and shooting it over the scrambling goalie.

The goal immediately deflated Sabres fans, but replays made them seethe. The video and still photos revealed that Hull’s left skate was in the blue paint of Hasek’s crease as he kicked the puck, apparently violating a frequently enforced rule that read: “Unless the puck is in the goal crease area, a player of the attacking side may not stand in the goal crease. If a player has entered the crease prior to the puck, and subsequently the puck should enter the net while such conditions prevail, the apparent goal shall not be allowed.” However, few people knew that the league had quietly circulated a memo earlier that season explaining that an attacking player’s skate could be in the crease as long as he maintained control of the puck through the entire sequence.

The NHL’s official explanation: “A puck that rebounds off the goalie, the goal post or an opposing player is not deemed to be a change of possession, and therefore Hull would be deemed to be in possession or control of the puck, allowed to shoot and score a goal even though the one foot would be in the crease in advance of the puck. Hull had possession and control of the puck. The rebound off the goalie does not change anything. It is his puck then to shoot and score albeit a foot may or may not be in the crease prior to.

“Did he or did he not have possession and control? Our view was yes, he did. He played the puck from his foot to his stick, shot and scored.”

Of course that did not sit well with Buffalo’s players or fans. The Sabres remained in their dressing room for 20 minutes after the final horn expecting the goal to be overturned and they would be sent back out to keep playing. Fans chanted "No goal!" but the Stars ended up skating the Cup. Sports Illustrated’s story about the game referred to the controversial outcome as “the NHL’s worst nightmare.”

“I believe everybody will remember this as the Stanley Cup that was never won in 1999,” Sabres forward Joe Juneau said after the game. “It was given away to a good team, but the goal was not a legal goal.”

In triple overtime and on a questionable goal, losing like that is sheer heartbreak. — Sarah Kwak

• Philadelphia Flyers: May 26, 2000; Eastern Conference Finals, Game 7—Devils 2, Flyers 1

Sometimes the biggest punch to the gut is actually a gargantuan check to the head.

So it was in Philadelphia when Devils defenseman Scott Stevens knocked out Flyers captain Eric Lindros with a thundering hit early in the first period of the Eastern final’s decisive game. Lindros was playing in only his second game after sitting out 10 weeks with a concussion and now off he was off to the hospital, sidelined for the fourth time that season and taking Philadelphia’s hopes with him. The Flyers still managed to fight back after New Jersey took an early 1–0 lead. Winger Rick Tocchet tied the game, 1–1, on a second-period power play and sudden-death overtime looked imminent as the third period wore on. But with just 2:32 left in the regulation, Devils forward Patrik Elias snuck behind Flyers defenseman Dan McGillis, took a pass from Jason Arnott, and knocked the puck past goalie Brian Boucher. The Devils’ defense held and Philly’s 20,037 faithful in attendance suffered the further indignity of watching Stevens accept the Prince of Wales Trophy awarded to the Eastern champions. (No surprise that he was showered with boos.) 

To add insult to injury, the NHL fined the Flyers $10,000 for not divulging information about Lindros’s injury. It was a bitter end to a campaign that included coach Roger Neilson being stricken with cancer and the team rallying around interim bench boss Craig Ramsay. 

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For Flyers fans, the devastation of this particular defeat was three-fold: Losing such a high-stakes game in the final minute always stings a little more, but the Flyers, the East’s top-seeded team, shouldn’t have even been playing a Game 7 in the first place. They had squandered a 3-1 series lead, which back in those days was considered a stranglehold. Only 15 teams had ever overcome such a deficit. But the Flyers hadn’t played with urgency or a killer instinct in Games 5 or 6, even when Lindros returned, and they let the series slip away.

As much as losing Lindros stung, the pain only got worse. Game 7 proved to be his last as a Flyer. The star center sat out the next season with serious concussion issues and was traded to the Rangers in August 2001 after a bitter dispute with GM Bobby Clarke over his treatment by the team.

Once the great hope of a franchise seeking to recall its former glory, Lindros never fully delivered on his potential after he arrived in Philadelphia in 1992 as the celebrated “Next One”, a generational talent who would take his place alongside Mario Lemieux and Wayne Gretzky as a true superstar and champion. Though he led the Flyers to the 1997 Cup Final, they were swept by Detroit and that was as close as they would get to the chalice during his time wearing the orange and black. Sarah Kwak

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