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Top-3 Worst Free Agent Signings In Montreal Canadiens History



Montreal Canadiens buyout Karl Alzner

Current Montreal Canadiens general manager Kent Hughes has wisely avoided spending big money in free agency, especially when we consider that historically speaking, very few free agents end up providing long-term value to their teams.

Oftentimes, the situations in which the free agents played the previous season cannot be recreated with the new clubs, which was the case with former Canadiens players such as Mike Komisarek, Sheldon Souray, and Mark Streit.

Call it the Andrei Markov effect, if you will.

In retrospect, the aforementioned players owe Markov a gift for the rich contracts they signed with their new teams, but in this case, the usual thank-you gift, a Rolex, wouldn’t do.

Perhaps a helicopter built from Rolexs would be fitting.

With that in mind, let’s take a look at some of the worst free-agent signings in Canadiens history.

Honourable Mentions

One of the current members of the team, Mike Hoffman, ranks as one of the worst free-agent signings in team history.

Former general manager Marc Bergevin signed the winger to a three-year, $4.5 million annual average value contract, in a desperate attempt to re-tool his team for one last kick at the can.

Some may suggest Hoffman should be listed in the top-3, but despite his inability to identify his own goaltender in a police lineup, Hoffman has still provided the team with an average of 15 goals per season since his arrival.

You could also argue that former enforcer Georges Laraque ranks among the worst players the Canadiens signed, but given that he was only paid $500,000 per season in his two years with the team, you’d be hard-pressed to argue he should be in the top-3.

The same can be said about Alex Semin. He only spent 15 games with the team before they decided to terminate his contract.

When it comes to Daniel Briere, his short time with the Habs was definitely far from a success, though he did manage to score 13 goals in 65 games, which is reasonable production when you consider he was not receiving first-line minutes.

Unfortunately, Briere was offered a two-year contract which cost the team $4 million before they quickly traded him in the offseason for Colorado Avalanche forward P-A Parenteau.

3 – Brandon Prust

Bergevin wanted the Canadiens to become a more difficult team to play against.

But he didn’t want to sign any tough guy, he wanted a player that could also chip in offensively.

To do so, he turned to Brandon Prust, the rough-and-tumble forward who had spent the previous two seasons with the New York Rangers.

Prust was offered a four-year contract that came with a $2.5 million annual average value, which may not seem terrible on the surface, but when we consider that Prust had managed to score just five goals and 12 assists in 82 games the previous season, it’s rather clear that Bergevin overpaid to secure Prust’s services.

Not only did he give Prust too much money, but Bergevin also gave him too much term.

I’ll surely get some pushback by nominating Prust because he quickly became a fan favourite due to his style of play, but we also have to consider he his contract accounted for over 4 percent of the salary cap at the time, which is more than Kirby Dach’s deal accounts for in the current roster.

In today’s salary cap world, Prust’s contract would be worth almost $3.5 million per season.

The 28-year-old ended up scoring a grand total of 15 goals over three injury-filled seasons before he was traded to the Vancouver Canucks for Zack Kassian.

2 – Sergei Samsanov

Desperate for offensive talent, the Montreal Canadiens decided to sign a player who had spent the majority of his career with their greatest rivals, the Boston Bruins.

Forward Sergei Samsonov had recently been traded from the Bruins to the Edmonton Oilers in exchange for Marty Reasoner, Yan Stastny, and a second-round pick (Milan Lucic, 50th overall, 2006), entering the free agent market shortly thereafter.

And while it’s true that Samsonov was extremely talented, he ended up being one of the most disappointing signings in team history, not only because it came with a two-year, $7 million contract, but also due to Samsonov’s inability to generate any matter of sustainable offence in the offence-starved Canadiens lineup.

In 63 games with the Habs, Samsonov scored just nine goals and 17 assists.

Thankfully, the Canadiens did not dwell on their mistake, trading Samsonov to the Chicago Blackhawks in exchange for Jassen Cullimore and Tony Salmelainen.

1 – Karl Alzner

The Montreal Canadiens had a lot of big decisions to make in the summer of 2017.

There was the whole Andrei Markov and Alex Radulov fiasco, which led to the infamous line from Bergevin, “If you want loyalty, buy a dog.”

Things were further complicated when the team decided to offer Karl Alzner the type of contract that should be used in sports management courses as the perfect example of what not to do in professional sports.

Not only was he given a five-year contract, but the incredibly affable blueliner was also offered $4.625 million per season.

It was too much term and too much money for a defenceman who most analysts had already established as an overhyped player.

To make matters worse, the Canadiens put on a full-court press, wooing Alzner with a helicopter tour of the city in a desperate bid to convince him to sign with the team.

In retrospect, Alzner was an awful defenceman for $4.625 per season, but if he had signed for half that amount, he’d likely still be playing in the NHL.

At the very least, his reputation would not have been ruined to the point that it was following his assignment to the AHL.

We can’t blame Alzner for signing the rich contract, most players would have followed suit, but he did admit to me in later years that it was a mistake.

The type of mistake the Montreal Canadiens can no longer afford to make.

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Sean C.

Hoffman has been unimpressive, but the idea that is anywhere near one of the worst free agent signings in team history is ridiculous. A mediocre three-year contract isn’t anything of the sort.


I’d remove Prust and replace him with Laracque. At least Prust stuck up for his teammates. He didn’t ask the opposition for permission to fight.


I wouldn’t put  Brandon Prust at No 3, I think Mike Hoffman deserves that honour . we need a tough guy cuz the previous management didn’t adress it. I was ok with money part but he got one year too much. He got trade to Vancouver Canucks on his last year of that contract but spent most of the year in their farm club.


Prust wasn’t signed for his scoring. Your explanation doesn’t make hockey sense. Agree with the other two. Unfortunately, you left out about 90 years of Habs history. The headline is misleading.


Man, where is Scott Gomez? He should be number 1 by far. He got 7 mil per season and scored a grand total of 2 (two) goals in his last season

Robin Belinda

I agree that Mike Hoffman was a bad free agent signing, but only 3 players on the team had more goals than him and only 4 players on the team had more assists than him and he is still capable of scoring 20 goals. But I still agree that it was not a good signing.