Karl Alzner signed a monster five-year, $23.125 million contract on the opening day of free agency in 2017, and it quickly became the worst signing in the team's history.
The Montreal Canadiens do not have a long history of being a free agent hotbed. Big-name free-agent signings have always been rare for the Canadiens, who prefer to build through the draft and make timely trades. There have not been many egregious signings, but one signing in particular, Karl Alzner, stands out as the worst in team history.