Montreal Canadiens: 10 Worst Transactions Since Patrick Roy Trade

Nov 3, 2015; Denver, CO, USA; Colorado Avalanche head coach Patrick Roy reacts on the bench during a video goal review in the second period against the Calgary Flames at Pepsi Center. Mandatory Credit: Ron Chenoy-USA TODAY Sports
Nov 3, 2015; Denver, CO, USA; Colorado Avalanche head coach Patrick Roy reacts on the bench during a video goal review in the second period against the Calgary Flames at Pepsi Center. Mandatory Credit: Ron Chenoy-USA TODAY Sports /
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The Montreal Canadiens are a proud franchise with a rich history of stars and wins. They also have made some blunders along the way. Let’s take a look at some of the more recent head-scratchers.

The Montreal Canadiens have a long, storied history of success. They have the most Stanley Cups won, the most Hall of Fame players, the most wins in the history of the game. The most consecutive Cup seasons were five by the Habs from 1956-60.

The list of achievements goes on and on. However, every team has some skeletons in their closet. 21 years ago yesterday, the Habs made perhaps the biggest blunder in hockey history. Rejean Houle was the general manager of the team and overreacted to a spat between his coach, Mario Tremblay and his superstar goaltender Patrick Roy.

Roy was sent to he Colorado Avalanche, all but guaranteeing they would win the 1996 Stanley Cup. In return, the Canadiens got an underwhelming package of Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault.

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The trade put the Avs over the top and put the Habs into their darkest period in the team’s 107 year history. The Habs would not get past the second round of the playoffs for the next 14 years, and missed the postseason in four of five between 1999-2003.

The Roy trade set a new bar for terrible trades in the NHL. No one has matched it since, but not for lack of effort if you take a look at some of the head-scratching decisions made by those in charge of the Habs over the past 21 years.

Let’s take a look at the ten worst moves by the organization in the last 21 years.