The Montreal Canadiens have long been effective at drafting and developing players, but in the salary cap era have struggled on the UFA market in July, as you’re about to find out. Much like the New York Rangers, world class goaltending can really assist concealing mistakes. Bob Gainey held down the GM job for the first 5 years of the salary cap era, before retiring. Though if you analyzed some of the moves he made in his final 2 years, you’d be justified wondering why he didn’t get fired (which is not intended as slander against the man himself, just some curious transactions).
Gainey would be replaced by Pierre Gauthier, who did not survive long before being exchanged for Marc Bergevin, who was fired after a lengthy tenure. Bergevin made some shrewd moves, but was also responsible for some epic strikeouts, most especially Karl Alzner and Carey Price. Their best contracts list is dominated with shorter bridge deals, and here we’re seeing what was signed next, if the player was retained at all. This trend is shifting recently with Caufield and Suzuki. The Habs list ranked in the lower half for average badness, in part because Carey Price was stashed on LTIR and almost won the Cup, and PK Subban’s deal had good years but ended badly.
This was originally published in my 2020 book The Definitive Guide to Salary Mismanagement, and has now been updated with new contracts. I will continue to update each team’s list every summer going forward. The rule is that only active contracts can move up or down. Expired deals cannot pass each other (with a few exceptions). The book is still available on Amazon, though some of the stats on active contracts are now out of date. You may yet find it interesting because there were detailed stat graphics that you won't find here. One thing you won't find here are entry level contracts because they all come from the same cookie cutter and require less skill at the negotiating table.
1. Brendan Gallagher
Adjusted Cap Hit: $39.2M, $6.5M (avg)
Value Returned: $8.3M, $1.4M (avg)
% Earned: 21%
“I know nights that are a little tougher for him, but overall the effort's always there, the character is off the charts, and in the playoffs he's a guy that's always in the paint. He works hard, he gets loose pucks, he's not afraid of nothing, he just competes, night in, night out.”
Gallagher was very underpaid on his previous contract, so the only way Montreal could extend him was to offer a salary higher than what he’d likely get on the open market. There had already been a hometown discount, so Brendan wasn’t going to accept anything but a sweet deal to keep him off the market. The other option would have been to offer a lower cap hit but a full term. $39M over 8 years would have carried a $4.875M cap hit. More pain at the end, more manageable now.
Frankly the best option would have been to let him walk, as we’re talking about a very physical player with an injury history. There were some red flags, but the GM (who has since been fired) liked the player too much to see the forest through the trees. The maximum value of my E[FA$] algorithm in his career is $5.1M (in 2018/19), so at no point in his entire tenure has he even been close to a $6.5M player.
2. Karl Alzner
Adjusted Cap Hit: $24.2M, $4.8M (avg)
Value Returned: $5.7M, $1.1M (avg)
% Earned: 23%
“I’d love to go to the promised land with this team.”
Marc Bergevin knew he wasn’t buying offense when made this offer to Karl Alzner, and brought in a defensive defenseman to provide some relief for his goaltender. The plan backfired, as Price had the worst save percentage of his professional career with Alzner playing over 20 minutes per night for 82 games, scoring 12 PTS.
If you thought Karl’s first season in Montreal was a disaster, it only got worse in year two when he cleared waivers and was sent to the AHL. Karl was sent back to the minors in year three. Anytime you get this much money buried in the AHL, you messed up. The Washington Capitals won the Stanley Cup as soon as Alzner departed.
3. Carey Price
Adjusted Cap Hit: $85.5M, $10.7M (avg)
Value Returned: $19.4M, $2.4M (avg)
% Earned: 23%
“It's a great place for me. I have enough experience to deal with anything that being a goaltender for the Canadiens can throw at me. I never thought about putting on another uniform. I just thought it'd be too weird, I guess."
Carey Price signed this early extension prior to the 2017/18 season then proceeded to post the worst save percentage of his professional career. Had Marc Bergevin waited a little bit longer, the price would have dropped considerably (in theory). Instead, Carey became the highest paid goaltender in the league. The closest comparable is Henrik Lundqvist, who signed a similar deal 4 years earlier, that eventually turned sour in New York. This would also set the market for Sergei Bobrovsky 2 years later.
Price did rebound in year one of this deal, with 15 goals saved above average. His play came crashing back down to earth in year two, then helped make an unexpected run to the Stanley Cup final before suffering an injury. The goalie union may have celebrated when Price and Bobrovsky signed their massive contracts over the age of the 30, but the disasters that unfolded in the aftermath will undoubtedly decrease the likelihood of any goalie cashing in like this again. If the Habs can hide the rest on LTIR, then this is not as bad and needs to be lower on the list.
4. P.K Subban
Adjusted Cap Hit: $78.8M, $9.9M (avg)
Value Returned: $54.2M, $6.8M (avg)
% Earned: 69%
"A lot of people that know Marc Bergevin know the type of guy he is. He cares about his players, he cares a lot about his players, and I know he cares a lot about me. He would never put a player in a position that would hurt him or hurt this team and this organization. He's been great for this team moving forward, he's made some great decisions in the best interests of this team, and a lot of people have got to lay off of him now. I really don't want to hear those negative comments towards these guys because they've done a great job and they've worked so hard to try and get this deal done."
Marc Bergevin playing hardball to get PK onto a bridge deal backfired, as Subban won the Norris trophy and earned himself a preposterous pay raise. The GM probably never imagined that his 3rd contract would be this massive, but his hands were tied after Subban was named the best defenseman in the league. They made it all the way to arbitration, argued their sides, then came to this agreement while waiting for the arbitrator’s decision, making PK the highest paid defenseman in the NHL (which he remained until overtaken by Drew Doughty in 2019).
Subban was still among the league’s most prolific offensive defensemen early in this contract, but his output took a downward turn at age 29. He only lasted 2 seasons in Montreal on this deal before being traded to Nashville for Shea Weber, where he helped them advance to the Stanley Cup final in his first year in Tennessee. But once his output started to decline, the Preds dumped him on New Jersey, where PK hit rock bottom and helped Ray Shero get fired.
5. Jose Theodore
Adjusted Cap Hit: $30.3M, $10.1M (avg)
Value Returned: $7.2M, $2.4M (avg)
% Earned: 24%
"It sets a new standard for Group 2 goaltenders that are that young. But there are very few players that have won the Hart and Vezina at that age, so it will be very difficult for another player to get that same contract."
Jose Theodore was only 3 years removed from winning the Hart trophy as league MVP, so the big salary he was awarded by Bob Gainey made sense. If anything, the team dodged a bullet by only giving him 3 years term. Jose played only 38 games in Montreal on this contract with a 3.46 GAA and .881 SV%, before being dumped on the Colorado Avalanche for David Aebischer.
The trade came after it was revealed that he had failed a drug test, but being juiced up on hair loss medication certainly didn’t help him stop pucks. Theodore would later improve, providing league average goaltending for the Avalanche in year three, helping him get a new deal that you can read about on the Washington Capitals worst contracts list.
6. Jonathan Drouin
Adjusted Cap Hit: $34.4M, $5.7M (avg)
Value Returned: $16.8M, $2.8M (avg)
% Earned: 49%
"The chance to put your hands on a player like that, at that age, and a guy from here, I can't pass that up. We gave up a lot but I'm convinced we got back a big piece."
Jonathan Drouin scored at a 60-point pace with the Tampa Bay Lightning in the final year of his ELC, which prorated for 82 games, yielded an expected free agent value of $5.6M. Marc Bergevin saw him as the future number one centerman they desperately needed, so traded Mikhail Sergachev and a conditional second round pick to acquire Drouin. This contract was signed that same day, getting fair compensation based on the stat line. Unfortunately, a 60-point center is not what arrived at the Montreal airport.
Year one he scored 46 PTS in 77 GP and year two he scored 53 PTS in 82 GP. That’s as good as it got for Drouin as a Hab. In the next 3 seasons combined, Drouin scored 58 PTS, missing significant time with injury and illness while Mikhail Sergachev won a pair of Stanley Cups. That’s a loss.
7. Josh Anderson
Adjusted Cap Hit: $38.8M, $5.5M (avg)
Value Returned: $22.4M, $3.2M (avg)
% Earned: 58%
“It was a down year, and you never go into any year thinking that you’re going to get injured or things like that can happen. Obviously, in my contract year, it did. It started with Game 1, getting injured and me coming back early, which I said to myself I would never do again. And I got hurt again later on in the year and just decided that it was the best decision for myself to repair my labrum and make sure that I come back 100 per cent and have a long career.”
The Columbus Blue Jackets played hardball to force Josh Anderson to take a team friendly bridge deal, then in the final year, he battled injury and only produced 4 PTS in 26 GP. The team would have had the advantage in arbitration, but instead they opted to ship him to Montreal for Max Domi and a 3rd round pick. Shortly thereafter, Marc Bergevin signed him to a long-term extension at a cap hit that was about $900K higher than his career best stat line was worth.
Anderson is a high-volume hitter, and does provide a physical component that doesn’t show up on the scoreboard. For his first two seasons in Montreal, Anderson produced at around a $4M level, and if that was his cap hit, he would not be on this list. Not a catastrophic overpayment, but not good either.
8. Josh Gorges
Adjusted Cap Hit: $28.2M, $4.7M (avg)
Value Returned: $14.8M, $2.5M (avg)
% Earned: 52%
"I don’t think it’s Pierre Gauthier’s usual way to sign guys during the season but it’s more of an extension of negotiations from the summertime. I said right from the start this is where I want to be.”
Josh Gorges was set to become an unrestricted free agent at age 27 when Pierre Gauthier solicited his autograph on this extension before he could reach the open market. The offer needed to be substantial for Josh to punt on free agency, or at least decline listening to other offers.
He would go on to average 20 minutes per game over these 6 seasons, playing 337 games and scoring 49 PTS. That’s a bit pricey for a guy who specializes in hits and blocks. The Habs were able to dump him on Buffalo at age 30 for a 2nd round pick, and the Sabres were saddled with the brunt of his decline.
9. Michael Cammalleri
Adjusted Cap Hit: $40.6M, $8.1M (avg)
Value Returned: $30.5M, $6.1M (avg)
% Earned: 75%
“I can't accept that we will display a losing attitude as we're doing this year. We prepare for our games like losers. We play like losers. So it's no wonder why we lose.”
Mike Cammalleri landed on the UFA market following an 82-point season, cashed in, and never came close to that point total again. He suffered a knee injury in year one that cost him 6 weeks, but he managed to return and score 19 PTS in 19 playoff GP, helping the Habs advance to the Conference final.
His production would decline over the following 2 years and fans quickly forgot about that playoff success, as Mike became an unpopular and divisive player in Montreal. This led to him being traded in the middle of a game, going back to Calgary in exchange for a bad Rene Bourque contract and a 2nd round pick. He did manage to produce 215 PTS in 305 GP (58-point pace), the price was just too high.
10. Joel Armia
Adjusted Cap Hit: $13.7M, $3.4M (avg)
Value Returned: $4.8M, $1.2M (avg)
% Earned: 35%
Joel Armia reached peak production at age 26 in 2020, scoring at a rate of 42 PTS per 82 GP, averaging over 17 minutes of ice per game. Then in the 2021 pandemic shortened schedule, he regressed significantly down to 28 PTS per 82 GP and less than 15 minutes per night. Yet Bergevin in the summer of 2021 still decided to pay him at a rate proportionate to his 2020 numbers. Year one of this deal was even worse, producing just 19 PTS per 82 GP, which was worth substantially less than his salary. Year two was slightly better, but the production was still 1/3 of what you should expect from that pay grade.
11. Tomas Plekanec
Adjusted Cap Hit: $13.5M, $6.8M (avg)
Value Returned: $4.9M, $2.5M (avg)
% Earned: 36%
"The first thing you obviously ask yourself and talk about is, 'Do you want to stay in Montreal?' There was no question about that, so then they could start talking and make a deal."
Tomas Plekanec managed to sustain quality offensive production beyond his 30th birthday, prompting Bergevin to increase his salary on a 2-year extension. Lucky for Habs fans this was only a two-year contract, as Plekanec’s scoring output in year one dropped by almost half, down to 28 PTS in 78 GP, the lowest point total of his career at age 33.
While they may have paid approximately $6.7M (adjusted for cap inflation) for a player that was worth roughly $2.3M, the team was able to salvage some value by trading him to Toronto for a 2nd round draft pick, where he helped the Leafs lose to Boston in the first round. After this contract, Plekanec played 3 more games in the NHL before returning to Europe.
12. Brandon Prust
Adjusted Cap Hit: $12.4M, $3.1M (avg)
Value Returned: $4.2M, $1.0M (avg)
% Earned: 33%
“I think having me there is important and will make our jobs easier moving forward. That’s something I got out of our conversations. They wanted to add a bit of grit.”
Marc Bergevin knew exactly what he was buying when he signed Brandon Prust, as the new GM wanted to infuse more toughness into the roster. That’s why he also signed Francis Bouillon and Colby Armstrong the same day. Bergevin’s mistake was paying Prust twice as much as a bottom 6 grinder is supposed to be worth.
This was not a case where a player’s ice time or production dropped after a deal was signed, the price was just too high from day one. After 3 years in Montreal, Prust was traded to Vancouver for an overpaid Zach Kassian, who got into a car accident and sent to rehab before ever playing a game for the Canadiens. Prust only played a partial season in Vancouver before being sent to the AHL.
13. Jaroslav Spacek
Adjusted Cap Hit: $16.0M, $5.3M (avg)
Value Returned: $8.0M, $2.7M (avg)
% Earned: 49%
"We’re going to have to play big and smart, but this was a day where you had to grab talent where you can. There are other teams that don’t have anyone to announce."
The year 2009 brought with it perhaps the worst 48-hour stretch in Bob Gainey’s managerial career, when he traded Ryan McDonagh for Scott Gomez, then signed Mike Cammalleri, Brian Gionta (who was also nominated for this list) and Jaroslav Spacek as UFAs. Gainey would be gone from the Habs GM job less than a year later. Bob gave a 3-year deal to a 35-year-old Spacek thinking he was buying a 45-point defenseman. They received much less.
The Czech blueliner scored 21 PTS in year one, 16 PTS in year two. The final campaign was derailed by a series of injuries and the Habs were terrible. He was eventually shipped out of town for a bad Tomas Kaberle contract (which made Carolina’s worst list) and afterwards complained about the dysfunctionality of Montreal Hockey Operations. This proved to be the last contract of Jaroslav’s NHL career.
14. Erik Cole
Adjusted Cap Hit: $23.0M, $5.7M (avg)
Value Returned: $16.5M, $4.1M (avg)
% Earned: 71%
"It's my favourite building to play in. The feeling you get going into Montreal, the passion, the city, it just has an aura about it.”
Erik Cole became an unrestricted free agent at age 32 following a 26-goal, 52-point campaign, earning himself a 4-year commitment from Pierre Gauthier. Cole had a good first season before the lockout with 35 goals and 61 PTS. He became a very vocal critic of the NHL during the work stoppage, and “phoned in” the remainder of his career. Granted he was also 33 years old when the NHL locked out the players for half a season, so the production decline may have been attributable to natural causes as much as reduced effort.
The Habs managed to salvage some value from this debacle, trading him to Dallas for Michael Ryder and a 3rd round pick. The Stars managed to recover some value of their own, flipping to Detroit as a rental with a 3rd round pick in exchange for Mattias Janmark and a 2nd round pick. This marked the end of Erik’s NHL career.
15. Roman Hamrlik
Adjusted Cap Hit: $33.0M, $8.3M (avg)
Value Returned: $22.3M, $5.6M (avg)
% Earned: 67%
"Roman Hamrlik established himself as a solid NHL veteran. The acquisition of Roman fills a very important need in our organization. He is a strong defenseman with a powerful shot and excellent hockey skills. He brings to our club a solid experience and an excellent reputation"
Roman Hamrlik hit the free agent market after scoring 38 PTS and playing 24.9 minutes per game at age 32, securing a 4-year term at a high price tag. Roman immediately declined down to 26 PTS in year one, but the Czech defenseman still logged big minutes.
The Habs did qualify for playoffs every season, with Hamrlik playing a big role. By that standard of measure, this pact could be labelled a success. He wasn’t exactly “bad”, but was absolutely overpaid for the contribution he was making, like paying $8.2M for a D-man worth $5.6M. Roman managed to pull another decent contract after this at age 37, albeit for a significantly smaller salary.
16. Daniel Briere
Adjusted Cap Hit: $10.0M, $5.0M (avg)
Value Returned: $2.5M, $1.2M (avg)
% Earned: 24%
“Daniel showed a great desire to pursue his career in Montreal and we are very happy that he committed to playing in Montreal for the next two seasons”
Marc Bergevin inked Daniel Briere as an unrestricted free agent after he was bought out by the Flyers, following a disastrous 2013 season where he scored 16 PTS in 34 GP. The excitement of landing a French-Canadian sniper proved to be fleeting, as fans soon found out that Danny boy was no longer the player they thought he was, scoring only 25 PTS with 12.8 minutes of ice time per game in year one.
We later found out that Danny clashed with head coach Michel Therien, which may have contributed to his reduced deployment. The Habs managed to trade him to Colorado after just one season for a 5th round draft pick, and Briere was even worse for the Avs, so perhaps Therien was justified. 126 GP and 37 PTS (24-point pace) is certainly not what they paid for.
17. Sergei Samsonov
Adjusted Cap Hit: $12.5M, $6.3M (avg)
Value Returned: $5.0M, $2.5M (avg)
% Earned: 40%
"What Sergei lacks in size he more than makes up for in speed and tenacity. He definitely adds an important dimension to our lineup."
Sergei Samsonov scored 53 PTS in 74 GP coming out of the lockout (with an additional 15 playoff PTS during the Oilers run to the final) before reaching the UFA market at age 27. Injury issues in 2003 and 2004 may have made teams reluctant to offer him significant term, but he still managed to pull a big salary on a 2-year ticket.
The Russian winger’s scoring output and ice time tumbled immediately upon arrival in Montreal and the team put him on waivers in February of year one where Sergei went unclaimed. After the season they dumped him on Chicago for 2 players who would never play for the Habs. The Blackhawks would eventually send him to the AHL, where he was later claimed by Carolina on re-entry waivers. The Hurricanes re-signed him to a 3-year deal that produced mixed results.
18. Mathieu Dandenault
Adjusted Cap Hit: $12.4M, $3.1M (avg)
Value Returned: $5.1M, $1.3M (avg)
% Earned: 41%
“I’m not saying I want out, I’m just saying I don’t want to be sat out”
Mathieu Dandenault won a Stanley Cup with Detroit in 2002, and came to Montreal as an unrestricted free agent after the 2005 lockout. He produced one quasi useful season in 4 years and saw his ice time plummet in the 2nd half of his tenure as they moved him to the wing and started making him a healthy scratch.
In Jan 2008 he complained about being scratched and said “I’m not old. I’m not at the end of my career”. As it turned out, he was at the end of his career, and did not play any more NHL games after this expired.
19. Georges Laraque
Adjusted Cap Hit: $6.5M, $2.2M (avg)
Value Returned: $2.3M, $0.78M (avg)
% Earned: 35%
“A 10-year veteran, Georges is the kind of player who made his mark in the NHL. With his physical play and determination, we are convinced that he will add valuable energy to our group of players”
Georges Laraque was a Montreal born enforcer who went to the Stanley Cup final in 2008 with Pittsburgh, but did find himself as an occasional healthy scratch in the playoffs. Bob Gainey bestowed Georges with a generous 3-year ticket at age 31. This expenditure might have made sense off the ice from a marketing perspective with Laraque being a popular figure in Montreal, but on the ice it is not a sum that you should be paying for a “grocery stick”.
Laraque played 61 games before being bought out. Yes, he did have issues with herniated discs in his back, but it still would have been an overpayment had he been healthy. This was the last contract Georges signed in the NHL, retiring to join the Green Party, becoming their Deputy leader. He retired from that role before actually running for elected office.
20. Alexei Emelin
Adjusted Cap Hit: $19.0M, $4.8M (avg)
Value Returned: $9.9M, $2.5M (avg)
% Earned: 51%
Alexei Emelin was a hard-hitting defenseman with moderate offensive upside, at least for the two seasons preceding this contract. That’ also when the downward trajectory began, and the offense began to dry up, despite increases in ice time. The hitting continued at a high rate throughout these 4 years, but by year three Emelin contributed just 10 PTS in 76 GP, but it was good enough that Vegas was willing to take him in the expansion draft then flip him to Nashville for a 3rd round pick. Bad contract, but still in demand until the end.