Sidney Crosby and Henrik Zetterberg shake hands after Game 7 of the 2009 Stanley Cup Final.
Not every Detroit Red Wings fan has experienced all of the most heartbreaking moments, but that does not mean they didn’t happen—or hurt.
The Red Wings have missed the playoffs only twice in this writer’s lifetime, but there are still distressing moments that live in the darkest regions of Red Wings lore.
Detroit has shown the ability in recent decades to reload rather than rebuild.
When fans get accustomed to the success Hockeytown has enjoyed, they tend to take losses much harder. It’s like the cliche gods say, “the bigger they are, the harder they fall.”
This list has been measured by the significance of the stage, the manner in which it occurred and the level of devastation surrounding the loss. With that in mind, here are the five most heartbreaking losses in Detroit Red Wings history.
Vladimir Konstantinov was severely injured in a limousine accident following Detroit's championship in 1997.
While they do not translate into the criteria of this list, the loss of two key players off the ice still holds a spot in the heart of Hockeytown. They deserve recognition and fans everywhere will remember them how they were and love them as they are.
After Detroit’s Stanley Cup title in 1997, a limousine accident ended the career of Vladimir Konstantinov. It changed his life, the lives of his family, the organization and greatly affected the community.
Ansar Khan of mlive.com quoted former Red Wing forward Kris Draper:
You're on top of the hockey world, you're Stanley Cup champion, then the accident happened. It literally rocked our world. As excited as we were to win the Cup, it put everything in perspective, just how valuable life is.
Konstantinov spent weeks in a coma before recovering.
He still lives in Metro Detroit, and although his movement and speech are limited, he is conscious of his environment and still frequents Joe Louis Arena and the team.
On Nov. 21, 2005, Jiri Fischer collapsed on the Detroit bench and went into full cardiac arrest during a game against the Nashville Predators.
Team doctors applied CPR and used an automated external defibrillator to save Fischer’s life.
Fischer told Art Regner of foxsportsdetroit.com, “I don’t remember anything that happened on the bench that night against Nashville. I don’t remember any ambulance ride or doctors working on me.”
Fischer would not play for Detroit again, but remains with the team in his seventh season as the director of player development.
Fischer has never received a definitive diagnosis of a condition, but he is now healthy and happy with his role in the organization.
Detroit lost to Pittsburgh in Game 7 of the 2008-09 Stanley Cup Final.
Coming off their 2008 championship, the Red Wings returned to the Final against the same foe from a year before—the Pittsburgh Penguins.
Marian Hossa, a member of the 2008 Penguins, joined the Red Wings during the offseason in hopes to win a Stanley Cup and help Detroit be the first team to repeat since they themselves did it in 1997 and 1998.
With the series tied 2-2, Detroit won Game 5 at Joe Louis Arena 5-0 when Pavel Datsyuk returned from injury to play his first game of the series. With a 3-2 lead and all the momentum, it appeared Hockeytown would retain hockey's Holy Grail.
Pittsburgh won Game 6, forcing a pivotal Game 7 in Detroit. The Red Wings trailed 2-1, and with the goaltender pulled for the extra attacker, Penguins goalie Marc-Andre Fleury robbed Nicklas Lidstrom in the waning seconds to clinch the Stanley Cup for Pittsburgh.
Hossa recorded just three assists in the seven-game series and would sign with the Chicago Blackhawks in the offseason. The loss on the biggest stage stung Hockeytown, and they haven’t advanced beyond the second round since.
The New Jersey Devils' neutral-zone trap stymied Detroit on their way to a title.
The Devils were able to shut down Detroit’s formidable offense on their way to a Stanley Cup title—without ever having home-ice advantage in the playoffs.
The Red Wings were a heavy favorite over the fifth-seeded Devils and were outscored 16-7 during the four-game sweep. They were particularly over-matched in the final three games.
The series was over before the Red Wings ever knew what hit them.
Detroit had made the finals for the first time in 29 years, but the loss extended their championship drought to four decades.
Detroit trailed 3-0, but forced a Game 7 before falling short of making history.
The Detroit Red Wings met the San Jose Sharks in the playoffs for the fifth time, and second in as many seasons. The San Jose Sharks took a commanding 3-0 series lead winning all three games by one goal—two in overtime.
The Red Wings would storm back with three consecutive wins to force a decisive Game 7 in San Jose.
Detroit would come up short in Game 7, 3-2. Antti Niemi made 38 saves and Devin Setoguchi added a goal and an assist to eliminate Detroit for the second straight season.
Pavel Datsyuk scored another highlight-reel goal from an impossible angle to mount a comeback attempt, but it was too little too late for the Wings.
Detroit was on the cusp of history, but instead just another footnote and heartbreak in Hockeytown.
Jamie Baker scored the game-winning goal in Game 7 to eliminate the top-seeded Red Wings.
The San Jose Sharks were in their third year of existence and had finished an abysmal 11-71-2 the season before.
The Sharks finished the 1993-94 regular season 33-35-16, an NHL record 58-point turnaround, and earned the eighth seed in the Western Conference.
The Detroit Red Wings finished 46-30-8, were the top seed in the Western Conference, and were looking forward to cruising through the first round when they drew the lowly Sharks.
San Jose led the series 3-2 when Detroit won Game 6 at Joe Louis Arena in a 7-1 rout. With all the momentum and home ice for Game 7, the series was all but over.
With the game tied 2-2 in the third period Chris Osgood came out of his net to play the puck up the boards. The puck caromed off the wall directly to Sharks forward Jamie Baker who fired the puck into the gaping net before Osgood could recover.
The goal stood as the game winner and San Jose won 3-2, defeating Detroit in seven games to earn their first playoff series win in franchise history.
For Detroit, their 100-point season became a gut-wrenching loss, and the No. 1 team in the Western Conference suffered a historic first-round exit.
Jack Adams was suspended the final three games of the series, costing Detroit the title.
The Detroit Red Wings met the Toronto Maple Leafs to battle for Lord Stanley’s Cup.
The Toronto Maple Leafs had their first round bye, then defeated the top-seeded New York Rangers in six games.
Detroit took a commanding 3-0 series lead and was prepared to win the Cup at home in Game 4.
Trailing 4-3 late, referee Mel Harwood called successive penalties on Detroit’s Eddie Wares and Don Grosso, triggering an outburst from coach Jack Adams. Adams took a swing at Harwood on the ice and was suspended for the remainder of the Final.
Without their head coach, Detroit lost their composure and the final three games, marking one of the greatest comebacks in the history of sports.
To this day, only three other teams in the four major sports have come back from a 3-0 deficit to win a best-of-seven series.
Not only was it an epic comeback, but it is the biggest collapse and most heartbreaking loss in Detroit Red Wings history.