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.
Alzner was the fifth overall pick in 2007 for the Washington Capitals. He was a sturdy defensive defenceman, but contributed little on the offensive end. He spent parts of nine seasons with the franchise before electing to go to free agency because he was upset with the Capitals' shortcomings in the playoffs. On the opening day of free agency, Alzner signed a five-year, $23.125 million contract with the Canadiens as the team was looking to shore up their defence.
The deal was one of the biggest ones on the opening day of free agency, and for a one-dimensional player, it should have been obvious from the start that it was not going to work. Alzner's role was to provide defensive stability, but he could no longer perform at a high level, which became abundantly clear in his first season in Montreal. As the NHL evolved into a faster, more skilled game, his lack of mobility became a major problem. He finished second on the team in giveaways (70) and total on-ice goals against (94) in his first season with the Canadiens.
Adding insult to injury, the very next season, the Capitals, whom Alzner left believing they could not win, went on to win the Stanley Cup in his first season in Montreal. The Canadiens finished the season 26 points away from the final playoff spot, and Alzner was nearing the end of his time with the Canadiens after just one season.
At the start of the 2018-19 season, Alzner was a healthy scratch for the team's opener and a month later was placed on waivers. He went unclaimed and was sent down to the Laval Rocket, the Canadiens' AHL affiliate. That is pretty much the end of Alzner's tenure in Montreal. After playing in all 82 games in his first season with the team, he only appeared in 13 more games with the Canadiens before they bought out the rest of his contract on October 6, 2020.
The Canadiens got a full season and 13 games out of Alzner's big contract, and then they felt it was best for the team to pay him to stay home. Desperation is a team's worst nightmare, and that is exactly what this signing was. The team needed help on the blueline and overpaid for an ageing defenceman whose best skills were getting fazed out of the league. It is easily the worst free agency signing in Canadiens history.