Montreal beat writer isolates Patrick Roy's 1995 trade away from Canadiens that caused a major setback, as a deal Habs fans would overturn

Patrick Roy's jersey #33 is retired by both the Montreal Canadiens and the Colorado Avalanche. After his first eleven seasons with the Habs, the future Hockey Hall of Famer was expected to become a one-team legend, but a shocking trade in 1995 altered the course of both franchises.

In October 1995, then Canadiens president of hockey operations, Ronald Corey, fired incumbent general manager Serge Savard and head coach Jacques Demers after a 0-4-0 start to the season when the team earned 20 goals against. Roy's relationship with the new head coach, Mario Tremblay, was rocky from the beginning.

It reached a tipping point when, during a game against the Detroit Red Wings on Dec. 2, 1995, Roy was kept in goal against a rampant offense that scored nine against him. When he was pulled, on the way to the dressing room, ignoring Tremblay, he told Corey that he had "played [his] last game in Montreal."

On Dec. 6, general manager Rejean Houle traded Roy to the Avalanche along with captain Mike Keane for goalie Jocelyn Thibault and forwards Martin Rucinsky and Andrei Kovalenko.

According to The Athletic's Apron Basu, in their column on Nov. 22, the Canadiens trading Roy was their most regrettable trade, one that they would want to undo the most.

"This is not a particularly hard choice. The Roy trade set the franchise back for at least a decade, and perhaps even more," he wrote. "This was always seen as a side effect of then-team president Ronald Corey’s decision to fire coach Jacques Demers and general manager Serge Savard and replace them with Mario Tremblay and Réjean Houle, but the reality is that Savard was already contemplating trading Roy. The Canadiens simply had to get a higher-quality return."

Looking at Canadiens and Avalanche's history during Patrick Roy's years

When he played his first season as the primary goaltender for the Canadiens, in 1985-86, Roy led them to an unexpected Stanley Cup win. He repeated the feat in 1993. He finished with a 289-175-66 regular season record and 70 wins in the playoffs.

The Habs went through a period of irrelevance immediately after the trade. They made it to two conference semifinals and one quarterfinal while missing the playoffs altogether in four seasons in the following eight years.

Meanwhile, Roy found immediate success in Colorado, winning the Stanley Cup in 1996. From 1998 to 2002, they made at least the conference finals in every season while winning the Cup in 2001. Roy retired in 2003 after a first-round exit to the Minnesota Wild.

Patrick Roy won the Conn Smythe trophy a record three times as he remains the only player to do so for two different teams.

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Edited by R. Nikhil Parshy