Puck Daddy's Summer of Disappointment: Montreal Canadiens Edition

(Ed. Note: There’s entirely too much sunshine in the summer. So your friends at Puck Daddy are offering a month of thrown shade and perpetual gloom. Behold, our Summer of Disappointment series, in which we ask fans of all 30 teams to recall the biggest bummer moments, teams and players in franchise history! Please wade into their misery like a freezing resort pool, and add your own choices in the comments!)

Written by Ian Hermelin of The Breakdown

Most Disappointing Team: 1969-1970 Montreal Canadiens

The NHL doubled in size leading up to the 1967-1968 season.

The Canadiens, fresh after falling to the Toronto Maple Leafs in the previous seasons' Stanley Cup Final, looked to re-assert their dominance on the new league. They did just that, capturing their 15th and 16th Stanley Cups in 1968 and 1969.

Riding high on that success and with a roster proliferated by future hall of famers, the Habs looked to continue their command as the league's preeminent franchise.

What happened instead was a failure to make the playoffs for the first time in 22 years.

In Montreal, missing the playoffs was unacceptable - let alone for a team coming off of two consecutive Stanley Cups. In the final game of the season, the Blackhawks came to the Montreal Forum. With the Habs trailing 5-2, Coach Claude Ruel needed to think outside the box.

Unlike Patrick Roy and Dallas Eakins in 2013-2014, Ruel pulled his goalie with 9 minutes and 30 seconds left to play.

Chicago would score five empty net goals and win the game by a score of 10–2. Ruel would step down 23 games into the following season, and the Habs would go on to win their 17th Stanley Cup.

Most Disappointing Canadien: Doug Wickenheiser

You might be asking, how can a player who played over 500 games in the NHL and scored over 100 goals be a disappointment.

While those numbers are certainly not the least respectable career stats in the history of NHL resumes, much more was expected when the Canadiens drafted the Major Junior star out of Regina with the first overall selection in the 1980 NHL entry draft.

Wickenheiser was a superstar in Major Junior hockey with the Regina Pats, leading the WHL in goals with 89 in 1979–80. He was the CHL Player of the Year, and captained his team to the Memorial Cup before being rated as the top draft prospect by The Hockey News.

With the draft being held at the Montreal Forum, many Hab fans were clamoring for the Canadiens brain trust to land local Junior standout Denis Savard. The Canadiens would try to rectify this blunder by drafting Louis Leblanc with their first selection at the 2009 draft in Montreal, that pick seems to have worked out about as well as Wickenheiser.

Years later, the Canadiens would finally land Denis Savard towards the end of his career. Savard would put up 179 points in 210 games with Montreal - 54 points and 8 games better than Wickenheiser's short-lived stint, further cementing the legacy of Doug Wickenheiser as the biggest letdown to ever play for les Glorieux.

Most Disappointing Moment in Canadiens History: April 13th 2004 - Mike Ribeiro's "Pinched Nerve"

Something about the local boy always rubbed me the wrong way, but it wasn't until he flopped around like he had just been hit by a bullet from an assassin's rifle that I really took a strong disliking to Mike Ribeiro.

Longtime Journal de Montreal Columnist Bertrand Raymond at the time said that what Ribeiro did was "embarrassing for the (Canadiens') organization and for the sport. He showed a lack of respect for all who practise the same profession."

Ribeiro for his part said it was a pinched nerve. Whatever the case may be, a wink and a smile at the opposing bench after only made matters worse. Any fan of the Habs at that time was beyond disappointed, they were embarrassed by a display usually reserved for the soccer pitch.

Most Disappointing Canadiens Transaction: Chris Chelios for Denis Savard

So much ink has been spilled on this trade and the 1995 trade of Patrick Roy that nothing new can be added to the subject.

While the trading of Chris Chelios did not set back the franchise the same way the trading of Roy would five years later, the general manager orchestrating this deal (Serge Savard) should have known better.

Chelios was a 28 year old defenseman with a reputation for partying. Canadiens brass didn't like the way that image represented their brand and decided to divest themselves of an asset. They felt that they could use Chelios to right a previous wrong and pry Denis Savard out of Chicago.

Denis Savard had a relatively productive, albeit short, stint in Montreal producing slightly under a point per game in three seasons. He would also be a part of the Canadiens 24th Stanley Cup in 1993.

Chris Chelios, would play twenty more seasons in the NHL, winning two Stanley Cups, an Olympic silver medal, and two Norris Trophies. He would also be a nine-time all-star (4x First Team, 1x Second Team).

While those honours would mark a sterling career for most players, Chelios had already been a two-time all-star en route to winning a Stanley Cup and a Norris Trophy in Montreal; feigning ignorance on a player entering his prime at 28 years of age makes the trading of Chris Chelios the most disappointing transaction in the history of the Canadiens.

Most Disappointing Canadiens Coach/Executive: Bob Gainey

In 2003, Habs brass felt it was time to bring the luster back to the CH. Their answer was to push Andre Savard aside for a repatriated Bob Gainey.

Before returning to Montreal, Gainey had molded the Dallas Stars into a well-coached, competitive team, culminating in a Stanley Cup in 1999. The Stars of Bob Gainey and post-Gainey would dominate the NHL's central division for over a decade. Who better than this shrewd hockey mind and former captain to lead our team to glory?

Gainey spoke of a five-year plan back to the Stanley Cup when he was hired. Hopes were high. The team never delivered. In year six of the five-year plan, the Canadiens would finish atop the Eastern Conference, only to fizzle out in the second round of the playoffs.

The following season, a rash of injuries and a room divided led Gainey to let much of the core of his team walk in free agency. Gone were the likes of Alexei Kovalev, Mike Komisarek and beloved captain Saku Koivu. The five-year plan had failed. Gainey's answer was to throw money at every available free-agent on the market and see what happened.

While the 09-10 Canadiens "Science Experiment" (as-so coined by Pierre McGuire) turned out to be a success with the team reaching the Eastern Conference final, this was more a lucky accident than a genius masterstroke.

Shortly after that Gainey resigned his post, failing to deliver on his promise and the excitement his hiring had created all those years prior.

Most Disappointing Canadiens Fashion Choice: The 1912-1913 Barber Shop Jerseys

Just no.

The bad luck aside, these things were an eyesore that belonged buried in the past. The Canadiens jersey and logo are both iconic and bringing in this eye-sore for a cash grab was just awful.

They did serve their barber shop purpose and SHAVE Robert Lang's Achilles tendon, effectively ending his Canadiens' tenure.

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Other disappointments (in order of appearance): New York Rangers • Calgary Flames • St. Louis Blues • New York Islanders • Dallas Stars • Boston Bruins • Colorado Avalanche • Washington Capitals • Ottawa Senators • Arizona Coyotes • Minnesota Wild • Edmonton Oilers • San Jose Sharks • Winnipeg Jets • New Jersey Devils • Los Angeles Kings • Florida Panthers • Carolina Hurricanes • Buffalo Sabres • Tampa Bay Lightning • Chicago Blackhawks • Columbus Blue Jackets • Nashville Predators • Detroit Red Wings • Anaheim Ducks • Philadelphia Flyers • Pittsburgh Penguins • Vancouver Canucks • Toronto Maple Leafs