The Montreal Canadiens have not won a Stanley Cup since 1993. That is a drought that is sure to reach 30 years following the upcoming season, a season in which they are more likely to finish last then first.
They did have some opportunities to end that Stanley Cup drought in the past three decades. They did still have a pretty good squad in 1994, backed by Hall of Fame goaltender Patrick Roy, but he was injured late in a series against the Boston Bruins and the Habs were eliminated early.
Many of their playoff successes since have come because of great goaltending. The team has been as far as the conference finals on three occasions since their last triumph. Each of those playoff runs was attributed to their goaltender playing at a ridiculous level for an extended period of time.
The first lengthy playoff run since 1993 was in 2010 when an unproven Jaroslav Halak carried the team past the Washington Capitals and Pittsburgh Penguins in thrilling seven game victories before bowing out in round three. The Habs were vastly outplayed in almost every game, but Halak was sensational, stealing the series from the Caps and Pens.
The Habs had another playoff run in 2014 when Carey Price was at the top of his game. He was lights out in series wins over the Ottawa Senators and Boston Bruins, before being injured in Game 1 against the New York Rangers in the Eastern Conference Final.
The Canadiens made it all the way to the Stanley Cup Final in 2020, with Price once again playing to an extremely high level. This time, the team in front of him played quite well too, but the Habs were no match for the Tampa Bay Lightning in the final round.
Goaltending is an essential component of an NHL team, and the Canadiens had a great one in Price for a decade. There were other chances for the Canadiens to make long playoff runs, but they never really pushed their chips into the middle of the table during Price’s entire career.
With Price sitting out this season, it looks like his playing career is over. Looking back at his time with the Canadiens, there are three instances that stand out as missed opportunities for the Canadiens who should have been more aggressive in trying to win when they had a stellar goaltender in their crease.