Habs Hits and Misses: Montreal’s Most Painful Contracts Since the ’90s

The middle of summer is here, and yes folks, it’s that time of year when the hockey world drifts into its sleepy season. The last remaining UFAs are left wondering if their next stop will be the Buffalo Sabres… or the Hamburg Crocodiles (yes, that’s a real team—Sens legend Christoph Schubert ended his career there). Or maybe somewhere far-flung with an ä in the name, like Jyväskylä umm …that’s an a-umlaut, by the way, the letter, not the team.

But enough Euro-linguistics. What got me going was the freshly released list of the NHL’s worst contracts, ya know, every team’s got one. Those David Clarkson-esque blunders that make GMs look like they believed they were one free agent away from hoisting Lord Stanley, or one Marc Bergevin teary Gallagher presser away from solving it all.

So here’s my little thought experiment: what’s the worst Canadiens contract of each era, starting from the ’90s? Why not earlier? Because I’m not about to dunk on a guy who drove a Chevrolet Caprice to the Forum, made $100K, and chipped in 10 goals. Sorry, Bob Gainey circa 1989—you may have been ‘Guy Lafleur’ overpaid and on your last legs, but you’ll always be my guy.

1990s – Trevor Linden

Ah, the late ’90s. Baggy jerseys, tiny logos, getting Habs autographs at Zellers, Saku Koivu’s refusing to speak French, Brian Savage scoring 29 goals in October and zero the rest of the year, and a new millennium just around the corner. In 1999, the Habs brought in Trevor Linden from the Isles on a four-year deal worth $14 million. Linden was a class act; unfortunately, the class was mainly about not making the playoffs, but in Montreal, he was more “solid citizen” than “Vancouver franchise saviour Linden,” putting up 30–49 points a season before being shipped out in 2001 for Richard Zednik and future Canucks legend Jan Bulis. For that kind of money back then, you wanted a 70-point guy, not a polite 3rd-line centre who blended in like beige paint.

2000s – Sergei Samsonov (with a side of Scott Gomez)

In 2006, Montreal rolled out the red carpet for Samsonov: two years, $7.05M for a player whose best years in Boston were already in the rearview mirror … In this case, more like running over a deer and staring at it in the rearview mirror. He rewarded the Canadiens with nine goals in 63 games before being waived, then traded. It was the free agent equivalent of buying a flashy used sports car that immediately needs a new transmission.

And then, 2009 gave us The Gomez Contract Era. To be fair, the Habs didn’t sign it, they traded for it,  but that $7.37M cap hit was a millstone. Gomez famously went a full year without scoring a goal, which in Montreal is like being a poutine chef who forgets the cheese curds.

2010s – Karl Alzner

July 1, 2017. Five years, $23.125M. Bergevin wanted stability on the blue line, so he signed Karl Alzner, a shot-blocking iron man from Washington. Within months, Alzner was a healthy scratch, then riding buses in Laval. By 2020, the Habs bought him out, leaving a neat little dead-cap souvenir. It was like ordering a steak dinner and getting served a corn cob with no corn on it — still technically food, but not what you paid for.

2020s – Brendan Gallagher and Josh Anderson

Gallagher’s six-year, $6.5M AAV extension (signed in 2020) was meant as a reward for years of heart-and-soul play. But his body has taken a beating (do not Google Gallagher fingers) and injuries have turned that contract into a warm, fuzzy albatross. We all still love him, though, right??? He’s my new 1989 Bob Gainey.

Ok … but what’s the takeaway … Well …The Habs’ history books are filled with glorious trades, shrewd signings… and the kind of contracts that make you stare at CapFriendly at 2 a.m. wondering, “Does the SQDC have edibles?”

For the Canadiens, the culprits change from decade to decade, but the theme stays the same: a mix of wishful thinking, bad timing, and the eternal GM belief that this will be the guy who changes everything. Sometimes it works. Sometimes you get Karl Alzner in the AHL with 12 points in 54 games.

And who knows? Maybe the deals we’re side-eyeing today — Gallagher, Anderson — will look better in hindsight. Or maybe, five years from now, we’ll be adding a new name to this list, shaking our heads and laughing.

Because if there’s one thing more certain than bad contracts, it’s that Habs fans never forget them.