Top 10 Most Painful Chokes in NHL History

To have something within grasp but not able to reach it that is one of the most frustrating things in sports. Here are some examples of such pain from the ice rink.
The Top Ten
Tampa Bay Lightning, 2018-19

For non-hockey fans, imagine if the 2007 Patriots that went 16-0 lost in their first playoff game to the Jaguars by 30+ points. That is the equivalent to this.

There are three types of chokes in sports: a great regular season team folding in the playoffs, blowing a series lead, and blowing a lead in an individual game. The Falcons in Super Bowl LI are the biggest blown game lead choke. The Yankees in the 2004 ALCS are the biggest blown series lead choke. In my eyes, the 2019 Lightning are the biggest playoff underachieving choke.

This team tied the league record for regular season wins and got swept in the first round by a team that had never won a playoff series in its existence. That level of choking seems impossible, but Tampa Bay sure pulled it off.

San Jose Sharks, 2013-14

The 2013-14 San Jose Sharks dominated the Los Angeles Kings early in the series, outscoring them 13-5 through the first two games. They then went to LA and stole a game in overtime to go up 3-0 in the series. The Kings regrouped and dominated for the next four games, outscoring the Sharks 18-5, and won the series in seven games. The Kings went on to win the Stanley Cup that year, and it all started with the Sharks choking in round one. You thought 2009 was bad. This was even worse. It was like two completely different teams.

Detroit Red Wings, 2005-06

The amount of talent this Red Wings team could boast was insane. During the 2005-06 regular season, the Wings had one of the most dominant seasons in NHL history. They won the Presidents' Trophy with 124 points and had only a single regulation loss in their final 20 games. Everything seemed to be lining up for them. This was their moment - or not.

The Wings' lineup included four future Hall of Famers and four players with at least 80 points. The Oilers were outshot 238-155, but none of that mattered as Edmonton won this series in six games and outscored the Red Wings 19-17. Led by trade deadline acquisition Dwayne Roloson, the Oilers rode his hot play all the way to the Stanley Cup Final, losing to the Hurricanes in seven games.

Toronto Maple Leafs, 2012-13

This series was a total roller coaster. When the Bruins took a 3-1 series lead in this first-round matchup, you'd think it was over. However, in typical Maple Leafs fashion, the team stormed back to tie the series only to lose in historically miserable fashion in Game 7. The Leafs took a 4-1 lead with ten minutes remaining. They seemed to be advancing to the next round, but against all odds, the Bruins won the game in overtime.

When I think of playoff chokes, I think of this one. Leading 4-1 with ten minutes to play - they had this one in the bag. There were plenty of Bruins fans that left the game before the Bruins came back and won it.

San Jose Sharks, 2008-09

The San Jose Sharks are a franchise known for playoff failure in recent memory, and this loss to the eighth-seeded Ducks was perhaps one of their biggest. The Sharks were coming off a Presidents' Trophy win during the regular season and were expected to roll throughout the playoffs. The stars had seemed to align perfectly until they ran into a hot Jonas Hiller and a team led by NHL superstars Corey Perry, Ryan Getzlaf, and Hall of Famer Scott Niedermayer.

They were shut out twice by Hiller during the series and lost this first-round match in six games. This one has to sting for San Jose.

Washington Capitals, 2009-10

The 2009-10 Washington Capitals won the Presidents' Trophy and boasted two 100-point scorers, Ovechkin and his partner in crime Nicklas Backstrom. The team also had two 40-goal scorers in Ovechkin and Alexander Semin, and five other 20-goal scorers. For comparison, the Habs' leading point scorer was Brian Gionta, who only managed 46 points. But the team had Jaroslav Halak, who slammed the door shut on the mighty Capitals and led his team to victory in seven games, with the Capitals blowing a 3-1 series lead.

Boston Bruins, 2009-10

The Bruins had the series under control, but Philadelphia had other plans. For only the third time in NHL history, and first time since 1975, a team came back from being down 3-0 in a series to win. Not only did the Flyers complete the unlikely comeback, but they also overcame a 3-0 deficit in the series-deciding seventh game. The Flyers were led by little-known goalie Michael Leighton, who was their backup, and he actually led them to the Stanley Cup Final, which the Flyers lost to the Chicago Blackhawks in seven games.

Detroit Red Wings, 2002-03

The Red Wings were blessed with four 30-goal scorers in a very low-scoring era. They were also stacked with seven future Hall of Famers and five multi-time All-Star game participants. None of this mattered whatsoever. All of that talent was wasted as the Ducks rode Giguere to a series sweep and all the way to the Stanley Cup Final, which they lost to the New Jersey Devils in a seven-game series. Giguere, however, was one of only five winners of the Conn Smythe Trophy as a member of the losing team.

The Ducks would win a Stanley Cup four years later. These Red Wings were defending champions, and to see them go down in just four games with all that talent is a major disappointment.

Toronto Maple Leafs, 2020-21

Toronto, you guys blew this series. It's that simple. Don't give me the excuse that your captain was hurt and you lost games 5 and 6. Great teams overcome all that. You guys didn't.

You won the worst division in the NHL - congratulations, I guess. It's been 54 years since you won, which ties the existing record in the NHL. You guys are failures. Imagine losing to the Montreal Canadiens, who were mediocre. They had all the heart and energy and outplayed y'all hands down.

Oh, and also, I don't want to hear another word ever again about how insert year is different or this is the Leafs' year. Y'all lost that right. Get humbled and silenced.

Edmonton Oilers, 1981-82

The Oilers were in the early stages of their dynasty, but still, with the talent they had, this was a bit disappointing. It was really the third game that summarizes this series in a nutshell: the "Miracle On Manchester," as it's called, for the amazing comeback that the Kings pulled off in Game 3. The Kings were down 5-0 at the end of the second period, but they ended up winning the game 6-5 in overtime. That victory put the Kings ahead 2-1 in the series, and they wound up defeating a heavily favored Oilers team that featured some of the best players in NHL history in five games.

The Newcomers

? Ottawa Senators, 2000-01

This may be more of an upset than a choke, but really this was like a walk in the park for the Toronto Maple Leafs. Led by an inspired performance by goalie Curtis Joseph, the Leafs were able to sweep the 109-point regular season Ottawa Senators - who had swept the regular season series - in four straight games. Joseph's game was so on point during this series that the Senators did not score their first goal until the final four minutes of Game 3. This was a pattern for the Sens of the early 2000s, who would always come up short when it mattered most.

? Boston Bruins, 2022-23
The Contenders
Edmonton Oilers, 2020-21

That was painful. The Oilers had a good regular season, and then they got swept by the Jets in round 1. It was quite painful.

Calgary Flames, 2018-19

This was pretty painful. The Flames had the best record in the West and won Game 1. Then the Avalanche won four straight. In Games 2 and 4, the Flames were winning, but then the Avalanche tied it late in the third period and won in overtime. It was super painful.

St. Louis Blues, 2020-21

That was painful to see. The Blues got swept by the Avalanche. It sucked.

Montreal Canadiens, 2020-21
Chicago Blackhawks, 2016-17
Calgary Flames, 2016-17
Vegas Golden Knights, 2018-19
Detroit Red Wings, 1993-94
New Jersey Devils, 1997-98
St. Louis Blues, 1999-00
Detroit Red Wings, 1994-95
Detroit Red Wings, 1941-42

They literally blew a 3-0 lead in the Stanley Cup finals. That's worse than anything.

Edmonton Oilers, 2019-20
Montreal Canadiens, 2015-16

That was pretty painful. They started the season 9-0-0 and then missed the playoffs.

Edmonton Oilers, 2016-17
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