Montreal Canadiens 15 Worst Contracts (2005-2022)

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. Next summer it may even be expanded to top 20. The book is still available on Amazon, though some of the stats on active contracts are now out of date.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.

My latest book The Hockey Economist’s Betting Prospectus is now available. It's a comprehensive commentary on the last 3 years of hockey betting, broken down by team, by category, by strategy, by season. There is plenty of useful information for bettors of all skill levels. It covers pre-pandemic, peak-pandemic, post-pandemic. What worked, what failed. Lessons learned, market trends, team-by-team analysis. What impact did the pandemic have on hockey betting? The market differences between these 3 seasons are discussed at length, and there's a lot to talk about. To read more, visit the Amazon store.

If you’d like to browse my other best/worst contract lists, click here. Enjoy! 

Please note: The formatting on the graphics got scrambled being copied from Excel into Google Blogger. It's among the reasons my blog is looking for a new home.

 
----------------

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 for personal reasons. Though if you analyzed some of the moves he made in his final 2 years, you’d be justified in wondering why he didn’t get fired.
 
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.
 
 
1. Carey Price
 

Signed By:	Marc Bergevin		Position:	G
Date:	2017-07-02		Age July 1st:	30
Term:	8 years		Playoff Wins:	13
Total Money:	$84M		Playoff SV%:	0.924
Cap Hit:	$10.5M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	10.6	154	75	2.66	0.911

“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

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.
 
 
2. Karl Alzner
 

Signed By:	Marc Bergevin		Position:	D
Date:	2017-07-01		Age July 1st:	28
Term:	5 years		Playoff GP:	0
Total Money:	$23.1M		Playoff PTS:	0
Cap Hit:	$4.6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	23.9	95	13	96
Per 82 GP	4.8	82	11	83	19.6

“I’d love to go to the promised land with this team.”

– Karl Alzner

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. Brendan Gallagher
 

Signed By:	Marc Bergevin		Position:	F
Date:	2020-10-14		Age July 1st:	29
Term:	6 years		Playoff GP:	0
Total Money:	$39.5M		Playoff PTS:	0
Cap Hit:	$6.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	39.5	56	24	142
Per 82 GP	6.5	82	35	208	15.0

“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.”

– Marc Bergevin

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.
 
 
4. P.K Subban
 

Signed By:	Marc Bergevin		Position:	D
Date:	2014-08-02		Age July 1st:	25
Term:	8 years		Playoff GP:	53
Total Money:	$72M		Playoff PTS:	32
Cap Hit:	$9M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	77.9	550	300	1227
Per 82 GP	9.7	82	45	183	23.4

"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."

– PK Subban

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
 

Signed By:	Bob Gainey		Position:	G
Date:	2005-09-02		Age July 1st:	28
Term:	3 years		Playoff Wins:	8
Total Money:	$16M		Playoff SV%:	0.904
Cap Hit:	$5.3M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	10.0	129	59	2.96	0.895

"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."

– Agent Don Meahan

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. Josh Gorges
 

Signed By:	Pierre Gauthier		Position:	D
Date:	2012-01-01		Age July 1st:	27
Term:	6 years		Playoff GP:	22
Total Money:	$23.4M		Playoff PTS:	2
Cap Hit:	$3.9M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	27.9	337	49	215
Per 82 GP	4.6	82	12	52	20.0

"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

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.
 
 
7. Tomas Plekanec
 

Signed By:	Marc Bergevin		Position:	F
Date:	2015-10-16		Age July 1st:	33
Term:	2 years		Playoff GP:	13
Total Money:	$12M		Playoff PTS:	7
Cap Hit:	$6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	13.4	155	54	283
Per 82 GP	6.7	82	29	150	16.0

"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

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.
 
 
8. Jonathan Drouin
 

Signed By:	Marc Bergevin		Position:	F
Date:	2017-06-15		Age July 1st:	22
Term:	6 years		Playoff GP:	6
Total Money:	$33M		Playoff PTS:	6
Cap Hit:	$5.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	34.0	263	157	543
Per 82 GP	5.7	82	49	169	16.9

"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."

– Marc Bergevin

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.
 
 
9. Josh Anderson
 

Signed By:	Marc Bergevin		Position:	F
Date:	2020-10-08		Age July 1st:	26
Term:	7 years		Playoff GP:	22
Total Money:	$38.5M		Playoff PTS:	6
Cap Hit:	$5.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	38.6	121	56	276
Per 82 GP	5.5	82	38	187	16.9

“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.”

– Josh Anderson

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.
 
 
10. Michael Cammalleri
 

Signed By:	Bob Gainey		Position:	F
Date:	2009-07-01		Age July 1st:	27
Term:	5 years		Playoff GP:	26
Total Money:	$30M		Playoff PTS:	29
Cap Hit:	$6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	40.1	305	215	879
Per 82 GP	8.0	82	58	236	18.8

“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

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.
 
 
11. Brandon Prust
 

Signed By:	Marc Bergevin		Position:	F
Date:	2012-07-01		Age July 1st:	28
Term:	4 years		Playoff GP:	29
Total Money:	$10M		Playoff PTS:	7
Cap Hit:	$2.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.3	207	52	185
Per 82 GP	3.1	82	21	73	13.0

“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.”

– Brandon Prust

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.
 
 
12. Jaroslav Spacek
 

Signed By:	Bob Gainey		Position:	D
Date:	2009-07-01		Age July 1st:	35
Term:	3 years		Playoff GP:	17
Total Money:	$11.5M		Playoff PTS:	4
Cap Hit:	$3.8M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	15.8	179	52	206
Per 82 GP	5.3	82	24	94	19.5

"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."

– Bob Gainey

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.
 
 
13. Erik Cole
 

Signed By:	Pierre Gauthier		Position:	F
Date:	2011-07-01		Age July 1st:	32
Term:	4 years		Playoff GP:	3
Total Money:	$18M		Playoff PTS:	0
Cap Hit:	$4.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	22.7	272	142	588
Per 82 GP	5.7	82	43	177	16.2

"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

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.
 
 
14. Roman Hamrlik
 

Signed By:	Bob Gainey		Position:	D
Date:	2007-07-02		Age July 1st:	33
Term:	4 years		Playoff GP:	42
Total Money:	$22M		Playoff PTS:	15
Cap Hit:	$5.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	32.7	312	119	501
Per 82 GP	8.2	82	31	132	22.7

"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"

– Bob Gainey

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.
 
 
15. Daniel Briere
 

Signed By:	Marc Bergevin		Position:	F
Date:	2013-07-04		Age July 1st:	35
Term:	2 years		Playoff GP:	16
Total Money:	$8M		Playoff PTS:	7
Cap Hit:	$4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	9.9	126	37	187
Per 82 GP	5.0	82	24	122	12.5

“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

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.

*

*

*

*