The Worst Montreal Canadiens Trades of All Time

This list of the Top Worst trades in Montreal Canadiens history is our third Worst Trades list, after the Worst 31 Trades in Maple Leafs history and the Worst 10 trades in Canucks history.

The trades on this list are ranked by Point Shares. For an explanation as to Point Shares and the rankings, see the Maple Leafs Best Trades list.

In Canadiens history, they have given up a whopping 1,222.67 more Point Shares than they’ve received back. So that’s a net of loss of nearly 4 Gretzkys worth of NHL players given up in trades over the years. That hurts.

For, the positive side, the Best 26 Trades in Canadiens History, see here.

So, without further ado, here are the worst Habs trades ever, ranked by Point Shares lost.

26. Reclamation Draft Deal – (25.1) PS

Canadiens get:

• Danny Geoffrion (in the reclamation draft) – (0.5) PS (6A for 6P, +1 in 32 GP)
• 1980 3rd Round Pick (John Newberry) – (0.1) PS (4A for 4P, +2 in 19 GP)
• 1981 2nd Round Pick (Lars Eriksson)

Nordiques get/keep:

• Alain Cote – 9.9 PS (103G, 190A for 293P, +22 in 696 GP)
• Richard David – (0.3) PS (4G, 4A for 8P, -7 in 31 GP)
• Mark Tardif – 14.9 PS (116G, 128A for 244P, -35 in 272 GP)

So this first one is a weird one. The Habs had the NHL rights to some Nordiques prior to the WHA-NHL merger and the Nordiques wanted the Habs to not take those players (especially 2-time WHA MVP Marc Tardif).

So on June 9, 1979 the Nordiques traded future NHL picks so that Habs wouldn’t draft Nordique LW Richard David or Nordique LW and former Hab Mark Tardif. Additionally, the Nordiques agreed to take LW Alain Cote, who was also a WHA Nordique, and the Habs agreed to take Boom Boom Geoffrion’s kid.

Both David and Geoffrion’s kid didn’t amount to much: David was an occasional role player for the Nordiques for a few seasons but soon found himself permanently in the AHL and Geoffrion was waived after just over 30 games.

Neither draft pick worked out. Newberry got a few cups of coffee but his contract was allowed to expire in 1985. And Eriksson never came over from Europe.

But Cote was a reliable bottom 6 played for the Nordiques for the entire decade. And though Tardif never remotely reached the heights he did in the WHA, he was a decent offensive player for the Nordiques for a few seasons, including 1981-82, when he scored 39 goals.

25. 3 Players for Perry Turnbull – (25.1) PS

Canadiens get: Perry Turnbull – 0.2 PS (6G, 7A for 13P, -11 in 40 Games)

Blues get:

• Gilbert Delorme – 5 PS (2G, 17A for 19P, -1 in 118 Games)
• Greg Paslawski – 14.3 PS (109G, 99A for 208P, -5 in 330 Games)
• Doug Wickenheiser – 11.2 PS (51G, 67A for 118P, +8 in 230 Games)

On December 21, 1983, the Canadiens decided to move on from one of the biggest draft busts in NHL history (and Haley’s cousin) by trading him, former 1st Rounder Delorme and Greg Paslawski for former 2nd overall pick Perry Turnbull.

The Habs drafted Doug Wickenheiser with the 1st overall pick in 1980. How did the best team of the 1970s have that pick? Through one of Sam Pollock’s numerous incredible heists.

However, Wickenheiser would become one of the great busts in the history of the draft, featuring on numerous Worst Draft Pick lists for years (though he has seemingly been forgotten as he’s not on as many lists as he used to be). In his first few years, Wickenheiser put up what would be decent numbers for a young prospect in the Dead Puck Era, but this was the 1980s and, after 200 games, the Habs were ready to move on.

Delorme had been drafted 18th overall in 1981, and had been fine so far. He might have been the real target of the deal for the Blues.

Paslawski was an amateur free agent signed before the 1981 season. He was probably put in the deal as an afterthought.

The 2nd overall pick in 1979, Turnbull, was off to a pretty good start to his career, having scored 139 goals prior to the trade. Now, he hadn’t done much else, but he was at least more of a scorer than Wickenheiser at this point.

But the trade didn’t make anything better for the Habs. Turnbull’s scoring plummeted on the Canadiens and they were done with him by the end of the season. Only six months later they traded him for Lucien DeBlois.

Delorme got off to a rough start with the Blues but then had a decent season the next year. But the Blues tired of him and traded him for Bruce Bell less than two years later.

Wickenheiser was not better on the Blues. The best season of his career was actually his final season in Montreal. But he was better than Turnbull, much better actually. He was waived in 1987.

Paslawski turned into a serviceable player for the Blues, scored 20 goals four times and coming within 1 goal of 30 in his best season. He was traded to the Jets in 1989.

24. Bourque for Cammalleri – (25.6) PS

Canadiens get:

• Rene Bourque – 2 PS (21G, 18A for 39P, -27 in 141 GP)
• Patrick Holland – (0.1) PS (0P in 5 GP, 0 in 5 GP)
• 2013 2nd Round Pick (Zachary Fucale) – 0 PS (0 GP

Flames get:

• Mike Cammalleri – 20.8 PS (89G, 89A for 178P, -34 in 216 GP)
• Karri Ramo – 16.5 GP (49-42-8, 5 SO, .911 SV%, 2.64 GAA)
• 2012 5th Round Pick (Ryan Culkin) – 0 PS (0 GP)

On January 12, 2012 the Canadiens traded 2010 playoffs hero Mike Cammalleri back to the Flames with goalie prospect Karri Ramo and a 5th Rounder, for Rene Bourque, prospect Patrick Holland and a 2nd Rounder in 2013.

Infamously, Cammalleri was traded mid-game. He had never played a full season for the Habs so it’s possible they were trying to get off of a player they assumed would not be healthy again.

Presumably, Bourque was the big asset coming back, coming off back-to-back 27-goal seasons. But he is actually older than Cammalleri and did not exactly have the same kind of career success as Cammalleri had. So it was a head-scratcher at the time. (Bourque was a College free agent so he entered the league in his age-24 season which might help explain why everyone thought Bourque was younger.)

Holland eventually made it into 5 games for the Habs but never scored. His AHL numbers were also middling.

After he was drafted, Fucale bounced up and down between the AHL and ECHL and never played an NHL game for the Habs. He eventually made the Capitals in 2021-22.

Worst of all, Bourque’s PPG plummeted, never matching even his worst season in Calgary and even scoring at a lower rate than he did for most of his years on Chicago. The Canadiens traded him to the Ducks two and a half years later.

Ramo was a middling 1A for the Flames. And the draft pick didn’t work out.

But Cammalleri was just as productive for the Flames in his second go-round as he had been for the Habs. (He didn’t come close to his first season in Calgary, however.) He left as a free agent in 2014.

23. Picks for Damphousse – (26.5) PS

Canadiens get:

• 1999 5th round Pick (Marc-Andre Thinel) – 0 PS (0 GP)
• 2000 1st Round Pick (Marcel Hossa) – 1.8 PS (10G, 9A for 19P, +2 in 59 GP)
• 2000/2001 2nd Round Pick (Kiel McLeod) – 0 PS (0 GP)

Sharks get: Vincent Damphousse – 28.3 PS (92G, 197A for 289P, +14 in 385 GP)

Damphousse spent over six seasons with the Habs, and led them to a Cup in 1993. But by the 1998-99 season, he was in his age-31 season, and the Habs were looking to rebuild.

So, at the 1999 Trade Deadline, the Habs traded him for 2000 1st, a 1999 5th and a 2000 or 2001 2nd Rounder. It seemed like a bit of a haul.

But the picks just didn’t convert. The 5th Rounder didn’t play a game, which isn’t a surprise, because they rarely do. Due to the terms of deal, the 2nd converted in 2001, but the Habs traded it to Columbus before that draft. The 1st was 16th overall but the Habs used it on Marian Hossa’s brother. (Like every star’s brother, he was nowhere near as good.) Marcel Hossa ended up being a disastrous pick, as he’s 39th in Points in his draft class.

And Damphousse became an important player for the early aughts Sharks, scoring 20 goals multiple times and helping them out of the first round a few times.

22. Bob Berry – (28.5) PS

Canadiens get: cash

Kings get: Bob Berry – 28.5 PS (159G, 191A for 350P, -7 in 539 GP)

Future NHL head coach Bob Berry had been signed by the Habs as an amateur free agent 1968. However, he only played two NHL games before the Habs decided to move on. (Berry had pretty decent AHL numbers that season.)

Berry played 7 seasons for the Kings with a career year of 36 goals and 64 points in 1972-73. The trade is on this list simply because the Habs got nothing back (in hockey terms).

21. Crutchfield for Cain and Conacher – (28.6) PS

Canadiens get: Nels Crutchfield – 0.2 PS (5G, 5A for 10P in 41 GP)

Maroons:

• Herb Cain – 13.5 PS (53G, 61A for 114P in 211 GP)
• Lionel Conacher – 15.3 PS (15G, 32A for 47P in 131 GP)

On October 3, 1934, the Canadiens traded Herb Cain and Canada’s Top Athlete of the First Half of the Twentieth Century for Nels Crutchfield.

Crutchfield was captain of the McGill Redmen and had helped the Redmen win the Allan Cup back in 1930 (when Canadian universities could still play for it). He had played Junior in Shawinigan and was from the Eastern Townships.

Cain was also a prospect, and was actually playing with Hector “Toe” Blake in Windsor. The Maroons had acquired both their rights. (A year and a half later, the Habs would acquire Blake from the Maroons in a much better trade, which ranks as the 8th Best Canadiens Trade of All Time by our estimation.)

The incredible Lionel Conacher may never have been the hockey player his brothers were – it’s hard to judge D from the ’20s and ’30s and his brothers were truly great forwards – but he was one of the greatest athletes in Canadian history (excelling at and winning in multiple different sports). He had already had a fine NHL career with the Pirates, Americans and Maroons (where he had been a 2nd Team All Star). Now he was just coming off winning the Stanley Cup with the Black Hawks, where he had made the 1st All Star Team and finished 2nd in Hart Trophy voting.

Earlier in day, the Habs had acquired Conacher in the franchise-resetting Howie Morenz trade. That trade wasn’t a good one for the Habs (partly because of this trade) but it wasn’t quite bad enough to make this list. (The Canadiens lost 19.4 Point Shares due to it.)

So the Habs traded a legendary athlete and now borderline-MVP defenceman plus a prospect for a prospect. It’s weird. In the Habs’ defence (sorry), Conacher had only recently been waived by the Maroons before his championship season with the Hawks.

Things didn’t work out.

Crutchfield, the local hockey star, ended up playing only 41 NHL games. A car accident ended his career before the next season could start. (Weirdly, he died in another car accident 50 years later.)

Cain and Conacher helped the Maroons to their second and final Stanley Cup.

Cain played with the Maroons until 1938, when he was traded back to the Canadiens. The Canadiens traded him to the Bruins a year later in another losing trade (nowhere near bad enough to make this list) and he gained infamy by leading the NHL in points in his 30s during one of the watered-down WWII seasons.

Conacher remained on the Maroons for the rest of his career. He made another 2nd All Star Team in his final season and once again finished 2nd in Hart voting. (Yes, that voting doesn’t make sense. How can you be runner up MVP but not even one of the best 2 D in the league?)

20. Green and Walter for 4 Players – (31.8) PS

Canadiens get:

• Rick Green – 23.8 PS (10G, 79A for 89P, +40 in 399 GP)
• Ryan Walter – 20.5 PS (141G, 208A for 349P, +11 in 604 PS)

Capitals get:

• Brian Engblom – 4.7 PS (5G, 23A for 28P, -10 in 79 GP)
• Doug Jarvis – 3.8 PS (31G, 81A for 112P, +9 in 265 GP)
• Rod Langway – 49.8 PS (25G, 177A for 202P, +116 in 726 GP)
• Craig Laughlin – 17.8 PS (110G, 173A for 283P, +17 in 428 GP)

One of the big trades that blew up the Habs dynasty of the ’70s, this one swapped much of the Habs defence for a little bit more offence on September 9, 1982.

Between them, Engblom, Jarvis and Langway had played an important role in 1-4 of the Habs most recent Cups. Laughlin had joined the team more recently as a role player, though he had been drafted in 1977.

Rick Green was the 1st overall pick in 1976 and had been providing steady D for the worst team in the league for six seasons. Walter was the 2nd overall pick a couple of years later, and he’d been a consistent 20-goal scorer since he came in the league. However, the season before this trade, he scored38 goals which is likely why the Habs thought his value was so high.

The trade wouldn’t have been a disaster for the Habs if they hadn’t given up so many players (well, if they hadn’t given up Rod Langway).

Green was a depth D for the Habs through the end of the decade, helping them to the 1986 Stanley Cup and the 1989 Finals. He was traded to the Red Wings in 1990.

Walter also contributed to those teams, though he was injured for most of the 1986 run. His best playoff run came the next season, when he scored 19 points in 17 games. But he never reached the heights of his best Capitals season and his first regular season for the Habs was his best in terms of offence. Despite scoring going up in the 1980s, Walter scored a substantially lower rate for the Habs. He left as a free agent in 1991.

The Capitals gave up on Engblom just over a year later, trading him to the Kings for Larry Murphy. (So, um, if we were doing a bigger trade tree, this transaction might look much worse.)

Jarvis may not have amassed a lot of Point Shares, but he won the Selke in 1984. The Capitals traded him after that Selke win..

Laughlin had some pretty good years for the Capitals, scoring 20 goals twice and scoring 30 in 1985-86.

But the reason this trade is such a lopsided victory for the Capitals, at least in terms of regular season wins, is Rod Langway, of course. In his first season after the trade he won the Norris. And then he won the Norris again the year after. And he finished 2nd in Hart voting. In total, with the Capitals, he won two Norris Trophies, finished Top 5 in Hart voting three times, and Top 5 in Norris voting an additional two times. He retired a Capital. Oops.

19. Bill “Red” Hay – (32.1) PS

Canadiens get: unknown players or cash

Black Hawks get: Bill “Red” Hay – 32.1 PS (113G, 273A for 386, +19 in 506 GP)

On April 27, 1959 the Habs traded centre prospect Bill Hay. Pro Sports Transactions says they got back some players but doesn’t specify who. Hockey Reference says it was cash. Either way, the Habs got no NHL players back in the trade.

And that’s bad because Hay immediately won the 1960 Calder. And he played eight seasons for the Hawks, helping them to a Stanley Cup in 1961. He retired a Black Hawk.

18. Ed Litzenberger – (34.4) PS

Canadiens get: cash

Black Hawks get: Ed Litzenberger – 34.4 PS (145G, 199A for 344P, -28 in 438 GP)

On December 10, 1954 the Canadiens gave Ed Litzenberger to the Chicago Black Hawks because they felt bad for them, or something. (Wikipedia says he was “donated” to the Hawks.)

Litzenberger was a wing prospect who had excelled for the Regina Pats in Junior. However, over his first two seasons with the Habs, he had only played in 5 games and had yet to break through. The Habs must have figured they wouldn’t miss him.

Litzenberger almost immediately excelled with the Hawks, winning the Calder and coming in second in scoring on the team, even though he only played 44 games for them. In 1956-57, he made the NHL 2nd Team behind Gordie Howe. And between 1954 and 1961, no other Black Hawk had more goals, assists or points and it’s not even close. (Litzenburger has 44 more goals, 55 more assists, and 110 more points than his teammates in 2nd.) He was literally the star of the team until Hull, Mikita and Pilote showed up.

However, by that time, Chicago had a new young core to build around and they traded him to Detroit during the 1961 off-season.

t-17. Zubrus and picks for Recchi – (34.8) PS

Canadiens get:

• Dainius Zubrus – 6.8 PS (29G, 45A for 74P, -11 in 139 GP)
• 1999/2000 2nd Round Pick Option (Matt Carkner) – 0 PS (0 GP)
• 2000 6th Round Pick (Scott Selig) – 0 PS (0 GP)

Flyers get: Mark Recchi – 51 PS (127G, 238A for 365P, +55 in 484 GP)

At the 1999 Trade Deadline, the Habs traded Mark Recchi for Dainius Zubrus, a 2nd Round option and a 6th Rounder.

Recchi had been acquired four years earlier in the infamous Desjardins trade (see below). But, though that traded didn’t work out, Recchi was still an extremely productive player. Between 1994 and 1999, Recchi led the Canadiens in points and goals.

Zubrus has been drafted by the Flyers in 1996 and was notably 10 years younger than Recchi. He had only had one good year for the Flyers but he was not yet 21 with 200 NHL games to his credit since the Flyers had brought him into the league immediately. The Canadiens clearly thought Zubrus would develop into something and the picks helped.

But things absolutely did not work out.

The 2nd Rounder, Matt Carkner, didn’t make the Habs and left as a free agent in 2001. The 6th Rounder, Scott Selig, only managed 33 games in the ECHL.

Zubrus, who was the highest Junior A player selected between the formation of the CJHL in 1993 and Kyle Turris in 2007, never amounted to whatever the Flyers thought they saw in him. But the Habs didn’t exactly wait to find out. Zubrus ended up playing fewer games with the Canadiens than he did with the Flyers. The Habs traded him almost exactly two years later, in the Richard Zednick deal.

Meanwhile, Recchi would go on to play for another decade. He would play with the Flyers until the lockout and during that time he would lead all Flyers in points and assists, and rank 2nd in goals. And the Flyers would make two Conference Finals, losing in Game 7 to the eventual Stanley Cup Champion both times. Recchi was far and away the best forward on the first of those two teams (the ’00 Flyers).

t-17. Phil Myre – (34.8) PS

Canadiens get nothing

Flames get: Phil Myre – 34.8 PS (76-95-32, 11 SO, .893 SV%, 3.21 GAA)

Phil Myre was the 5th overall pick in the 1966 Amateur Draft. Like many of the dearly drafts, there weren’t a ton of stars to emerge, partly because the process is very different than it is today. Brad Park, 2nd overall, is far and away the best player from this draft. At least by Point Shares, Phil Myre is second. (It’s worth pointing out that five skaters played in more games, but Hockey Reference values starting Goalies more than middle six forwards or 2nd or 3rd pair D.)

In the early ’70s, Myre was having trouble making the Habs full time. In his first season, he was behind Rogie Vachon, though he managed to play in more games than the ageing Gump Worsley. But in his second season, Ken Dryden showed up. And then the Canadiens drafted Michel Larocque, so that left Phil Myre as the odd man out.

Now, we’re cheating, because this was an expansion draft (the 1972 expansion draft to be precise), and he was just left unprotected, not traded. But Myre went on to be the Atlanta Flames’ starting goalie for six years. In 1973, he was one of the 10 most valuable goalies in the league by Goalie Point Shares (GPS) and in 1975 he was one of the 10 best goalies in the league by save percentage, GAA, shutouts and Goals Saved Above Average. He was traded to the Blues in late 1977.

Considering the Habs got absolutely no compensation for giving up a starter, even one who only had two good years, we have to view the decision to leave him unprotected as a mistake.

16. Thibault for Roy – (35.9) PS

Canadiens get:

• Andrei Kovalenko – 3.4 PS (17G, 17A for 34P, +9 in 51 GP)
• Martin Rucinsky – 30.4 PS (134G, 163A for 297P, -8 in 432 GP)
• Jocelyn Thibault – 26.6 PS (67-56-24, 7 SO, .908 SV%, 2.73 GAA)

Avalanche gets:

• Mike Keane – 2.8 PS (27G, 37A for 64P, +1 in 223 GP)
• Patrick Roy – 93.5 PS (262-140-65, 37 SO, .918 SV%, 2.27 GAA)

We thought this would be higher too.

And it would be higher – maybe even #1 – if Cups and playoffs wins were counted in our calculations. But since we’re going by regular season Point Shares, perhaps the most infamous trade in Canadiens history is only 16th on our list.

Everyone knows the story: Mario Tremblay was hired as the new coach even though he and Patrick Roy had never, um, gotten along. He left Roy in during a game in which he was getting shelled and, once pulled, Roy told management he was done.

So, on December 6, 1995, Rejean Houle, the man responsible for a number of trades on this list, traded Patrick Roy with fan favourite Mike Keane for young forwards Andrei Kovalenko Martin Rucinsky and goalie Jocelyn Thibault.

Kovalenko had put up okay numbers for the Nordiques and he continued at a similar pace for Montreal. But that was apparently not good enough and he was traded 9 months later to the Oilers for Scott Thornton.

Thibault would have had to set the world on fire to be popular in Montreal. But he was better than some fans probably remember, finishing 5th in GAA and 3rd in Save Percentage the season of the trade, and 10th Goals Saved Above Average and GPS in 1997. But he would never be Roy, and he was never, ever as good. He was traded to the Blackhawks three years after the deal.

Rucinsky had the most success for the Canadiens, scoring over half his career goals for the franchise. (All his 20 goal seasons were for the Habs.) After his trade to the Stars six years later, he would continue to have a reasonably productive NHL career for most of the next decade.

Mike Keane was briefly a valued role player for the Avs, helping them to the Cup in 1996. Winning two Cups on two different teams before he was 30 turned him into one of those “guys who could help you win” and the Rangers signed him as a free agent in 1997. (Later the Stars would target him at the trade deadline for that very reason.)

But the real story is Roy. He had nearly as many regular season wins in 8 years with Colorado as he did in Montreal. He made 1st Team All Star and won the Jennings. But, mostly importantly, he won two Cups, a Conn Smythe, and helped the Avalanche be one of the best teams of the subsequent decade.

15. 4 Players for Vachon – (36) PS

Canadiens get:

• Denis DeJordy – 0.1 PS (3-2-1, .860 SV%, 4.52 GAA)
• Dale Hoganson – (0.8) PS (2A for 2P, +9 in 46 GP)
• Doug Robinson – 0 PS (0 GP)
• Noel Price – 0 PS (0 GP)
• 1975 1st Round Pick Option (Pierre Mondou) – 38.5 PS (194G, 262A for 456P, +213 in 548 GP)

Kings get:

• Rogie Vachon – 75.5 PS (171-148-66, 32 SO, .901 SV%, 2.86 GAA)
• 1975 1st Round Pick (Tim Young) – 0 PS (0 GP)

On November 4, 1971, the Canadiens traded their former goalie of the future and a distant 1st round pick for four players and a pick in that same draft.

Vachon had been the Habs’ up-and-coming goalie, destined to replace Hodge and Worsley. He won a Vezina in 1968 (when it was still the Jennings) and he set the single-playoff record for save percentage in 1969.

But, by the time of this trade Ken Dryden had shown up, in the 1971 playoffs. So Vachon was rendered expendable. And so they tried to get something back for him, since he was good.

But Hoganson never scored a goal for the Canadiens, so Point Shares actually see him as a net negative player. He left for the WHA in 1973.

Price was returning to the Habs but never played for them this time. He was traded to the Flames less than a year later. And Robinson never played a game either. He was already 30 and finished his career in the AHL.

DeJordy was unable to secure a position as Dryden’s backup and was traded in the off-season to the Islanders.

But the pick…the pick turned into something. And had Vachon not had his Hall of Fame career or been traded to another team sooner, the Habs might have won the deal due to the pick. With it they drafted Pierre Mondou, who contributed to 3 of their 4 late ’70s Cups and scored 456 points.

Tim Young, the Kings’ pick from the trade, was, for a very brief period, a star, scoring 95 points in the 1976-77 season. But not for the Kings. The Kings traded him, inexplicably, straight-up for a 2nd Rounder in the next draft.

But Vachon cemented his Hall of Fame career while on the Kings. He made two 2nd Teams and finished 2nd and 3rd in Hart voting in those years. (Yeah, the voting doesn’t make sense. 2nb best goalie but 2nd best player???) By Goals Saved Above Average, his 1975 season, when he finished 2nd in Hart voting, is the 4th best season by a goalie ever. He signed as a free agent with Detroit in 1978.

14. Ted Green – (38.8) PS

Canadiens get nothing

Bruins get: Ted Green – 38.8 PS (48G, 206A for 254P, -47 in 621 GP)

Another cheater: on June 8, 1960, a day after reacquiring Green through the Intra-League Draft (i.e. waivers), the Canadiens lost Ted Green to the Bruins in the Intra-League Draft (i.e. waivers). You could argue we’re cheating extra hard here given that he was in Habs possession for a single day.

Green went on to a pretty successful career for the Bruins. He made the 2nd All Star Team in 1969 and somehow finished 3rd in Norris voting. (Behind Orr and Horton, in case you are wondering.) He made two All Star Games. He also helped the Bruins to the Cup in 1972. (If you’re wondering why he didn’t contribute to the Cup run in 1970, you can read about that here.) He then went on to success in the WHA, where he won three Avco Cups.

13. Niinimaa for Ribeiro – (42.7) PS

Canadiens get:

• Janne Niinimaa – 0 PS (3A for 3P, -13 in 41 GP)
• 2007 5th Round Pick (Andrew Conboy) – 0 PS (GP)

Stars get:

• Mike Ribeiro – 42.7 PS (123G, 284A for 407P, +16 in 461 GP)
• 2008 6th Round Pick (Matthew Tassone) – 0 PS (0 GP)

On September 30, 2006 the Canadiens traded Mike Rebeiro, who led the 2004 Habs in points, for D Janne Niinimaa. Ribeiro hadn’t scored as efficiently in 2005-06 as he had the season before, but Niinimaa was 31, coming off playing 14 minutes a game in the playoffs for Dallas, so it was a bit of a weird trade.

Neither pick amounted to any NHL games played, so they’re a wash.

After a very middling season for the Habs, in which he made it into only half the games averaging less than 15 minutes a game, Niinimaa signed with Davos in the off-season.

Meanwhile, Ribeiro became the #1 centre for the Stars. From 2006 to 2012, Ribeiro was 1st in Assists and Points and 2nd in Goals on the Stars. (He had 94 more assists and 79 more points than his next teammates.)

The Habs traded a #1 Centre (ish) for a third pair D (who essentially immediately retired).

12. Picks for Danny Grant – (44) PS

Canadiens:

• 1972 1st Round Pick (Jerry Byers) – 0 PS (0 GP)
• 1973 1st Round Pick (Bob Dailey) – 0 PS (0 GP)
• Player to be named later (Andre Pronovost) – 0 PS (0 GP)

North Stars get:

• Danny Grant – 34.2 PS (176G, 177A for 353P, +3 in 463 GP)
• Claude Larose – 9.8 PS (49G, 60A for 109P, -29 in 142 GP)
• Future Considerations (Bob Murdoch) – o PS (0 GP)

Note: There is a version of this trade with Marshall Johnston instead of Pronovost.

On June 10, 1968, the Canadiens traded long-time Hab and 3-time Stanley Cup Champion Claude Larose, and prospect Danny Grant, for some draft picks from a new franchise. This was a strategy that served the Canadiens extremely well many times throughout the 1970s but, in this case, it didn’t work out.

The picks didn’t work out: The Habs traded the 1972 1st Rounder back to the North Stars in 1971. And they traded the 1973 1st Rounder to the Canucks prior to that draft.

Pronovost didn’t work out either. He had won four Cups with the Habs in the late ’50s but he was done now, and his stint with with the North Stars had actually been an attempt at a comeback. (In the other version of this trade, Marshall Johnston wasn’t acquired until 1971, but then promptly sent to the Golden Seals. Either way, 0 PS acquired.)

The Canadiens sent Murdoch to the Stars to complete the trade in 1971 (at the same time they got either Pronovost or Johnston) but then promptly reacquired him from the North Stars in the Intra-League Draft.

Larose has the two best offensive years of his career for the North Stars, which makes sense due to the Canadiens’ legendary depth. The Habs reacquired Larose in 1970 (in a trade they actually won!) and he would go on to win two more Cups with the franchise.

Grant would become one of the first stars in North Stars history. In his first season with the team, he scored 34 goals and won the Calder. In his six seasons with the team, he only scored fewer than 29 goals once. Between 1968 and 1974, he was 1st in Points, and 2nd in Goals and Assists among all North Stars players. The Stars traded him in the 1974 off-season for Henry Boucha and Grant promptly scored 50 goals playing on Dionne’s wing (oof).

But just because the Stars didn’t get full value for Grant doesn’t mean they somehow lost this trade. The Habs gave up Grant and two players they later reacquired for literally zero NHL players.

11. Corson for Turgeon – (44.1) PS

Canadiens get:

• Murray Baron – 0.5 PS (1G, 5A for 6P, -16 in 60 GP)
• Shayne Corson – 13.3 PS (47G, 89A for 136P, -15 in 242 GP)
• 1997 5th Round Pick (Gennady Razin) – 0 PS (0 GP)

Blues get:

• Craig Conroy – 13.7 PS (57G, 94A for 151P, +41 in 359 GP)
• Rory Fitzpatrick – (0.3) PS (0P, -5 in 3 GP)
• Pierre Turgeon – 42.6 PS (134G, 221A for 355P, +65 in 327 GP)

On October 29, 1996 the Habs reacquired fan-favourite Shayne Corson for point-per-game player Pierre Turgeon. It didn’t go well.

Corson was drafted by the Canadiens in 1984. (Note that this trade occurred in 1996.) They traded Corson and a couple other players for Damphousse in what is our 13th Best Trade in Canadiens History. Now they wanted him back, apparently.

Baron was a long-time NHL D for the Blues, and previously for the Flyers. But he was a career minus player.

Fitzpatrick was a 2nd Round Pick in 1993. Conroy was a 6th Round Pick in 1990. Both had yet to make the NHL full-time.

Turgeon, on the other hand, was an NHL star. Now, he was a star known to be soft, but he was still a star, finishing Top 5 in Hart voting in 1993, and having scored 96 points the season before this trade. To make this trade more confusing, Turgeon had been made the team’s Captain the previous season, and, in the games right before this trade, had scored 11 points in 9 games.

Predictably, trading your Captain and best offensive payer for an older, middle-six winger who used to play for your team in the previous decade is a bad idea.

The pick didn’t turn into anything – Razin never made it out of the AHL and eventually returned to Russia.

Baron didn’t have a great start for the Habs and was traded at the very next deadline for Dave Manson.

Corson would score 20 goals for the Canadiens in his first full season back with the team (his best season since 1993-93) but after that his production fell off a cliff. (Though his PIM didn’t.) He signed with the Leafs as a free agent in 2000.

Fitzpatrick didn’t make the Blues either, and was waived in 1998. He was then reclaimed by the Bues two days later, but still didn’t make the team and was traded to the Predators in 2000.

But Conroy became a regular player on the Blues and finished Top 5 in Selke voting two seasons in a row. He was traded to the Flames at the 2001 Trade Deadline.

Turgeon was still a star on the Blues, leading the team in Goals, Assists and Points while he was there. (He has nearly 50 more assists than his next teammate and over 90 points.) The Blues made the Conference Finals in his final season with the team.

Another stellar trade by Rejean Houle.

10. A pick for Lumme – (46.8) PS

Canadiens get: 1991 2nd Round Pick (Craig Darby) – 2 PS (19G, 28A for 47P, -36 in 166 GP)

Canucks get: Jyrki Lumme – 48.8 PS (83G, 238A for 321P, +21 in 579 GP)

The Canadiens drafted Finnish D Jyrki Lumme 57th overall in the 1986 NHL Entry Draft.

After excelling in the World Juniors and in his post-draft seasons in Finland, he came over and played 21 games in the 1988-89 season, as well 26 games. The season of the trade, his numbers for the Habs were 1G, 19A for 20P, +17 in 54 games, in his age 23. season. The team decided they’d rather have a 2nd Round Pick. They wanted the bird in the bush, not the one in the hand.

With their 2nd Rounder, the Habs drafted Craig Darby in 1991. Darby made it into 10 games in the Lockout season before being lumped into the Muller-Turgeon trade, our 15th Best Canadiens Trade of All Time. So that outcome was positive at least.

Lumme played nearly 600 games for the Canucks. While he was with the Canucks, he led all Canucks D in Goals, Assists and Points. (He had more than 3 time as many goals as the next Canucks D in that era. And double as many points.) In their run to the 1994 Stanley Cup Finals, he had 13 points in 24 games. He was still playing Top 4 minutes into his 30s.

9. Gomez and Pyatt for Higgins and McDonagh – (47.2) PS

Canadiens get:

• Michael Busto – 0 PS (0 GP)
• Scott Gomez – 7.4 PS (21G, 87A for 108P, -23 in 196 GP)
• Tom Pyatt – (0.3) PS (4G, 8A for 12P, -6 in 101 GP)

Rangers get:

• Chris Higgins – 0.2 PS (6G, 8A for 14P, -9 in 55 GP)
• Ryan McDonagh – 54.1 PS (51G, 187A for 238P, +141 in 516 GP)
• Pavel Valentenko – 0 PS (0 GP)

One June 30, 2009, on the even of free agency, the Canadiens traded three-time 20-goal scorer Chris Higgins for former Calder-winner and New Jersey Devils #1 Centre Scott Gomez.

Higgins was coming off his worst full season as a pro. Gomez’s two seasons in New York were his worst, from an offensive production standpoint, since 2002-03. However, he still scored more than Higgins.

Busto was an amateur free agent who had yet to play with the Rangers and never played for the Canadiens.

Tom Pyatt was the 107th pick in the 2005 draft. He also had yet to play with the Rangers. He played fourth-line minutes for two seasons with the Habs and then signed with the Lightning in the 2011 off-season.

Gomez’s first season for the Canadiens was fine, offensively, producing at a clip similar to his last few seasons. But Gomez’s next two seasons were disasters, seeing the lowest production of his career. He was became a test case for the new CBA in 2013 and he was bought-out following a tweak to the new agreement.

Pavel Valenko was the Habs’ 5th Rounder in 2006. He never played in the NHL.

Higgins didn’t last long in New York. He was traded to the Flames for Olli Jokinen in early February of the subsequent season.

But Ryan McDonagh, the Canadiens’ 12th overall pick in 2007, became the franchise D for the Rangers. While there, he led all Rangers D in Goals, Assists, Points and, especially, Plus/Minus. (He had nearly double the goals of his next teammate. And more than 60 assists more than the next guy. His Plus/Minus over this stretch is over double that of the next Rangers D.) In 2014, he led the team to their first Stanley Cup Finals in 20 years, leading all skaters in ice-time and leading his team in points. He was traded the Lightning in 2018.

8. 1973 Pick Swap – (49.1) PS

Canadiens get:

• 1973 1st Round Pick (John Davidson) – o PS (0 GP)
• 1977 1st Round Pick (Mark Napier) – 25.2 PS (145G, 159A for 304P, +129 in 367 GPP
• 1978 2nd Round Pick (Dale Yakiwchuk) – 0 PS (0 GP)

Flames get:

• 1973 1st Round Pick (Tom Lysiak) – 36.4 PS (155G, 276A for 431P, +27 in 445 GP)
• 1973 1st Round Pick (Vic Mercredi) – (0.1) PS – (0P in 2 GP)
• 1973 2nd Round Pick (Eric Vail) – 38.4 PS (206G, 246A for 452P, +58 in 539 GP)

At the 1973 Amateur Draft, the Canadiens swapped a 1st Rounder they’d acquired from the Seals and their 1st Rounder, plus a 2nd Rounder, for the Atlanta Flames’ 1973 and 1977 1st Round picks, and a 1978 2nd Rounder. Like many other Habs trades of the 1970s, this was a bet that a new franchise would remain bad in the future.

The problem with this trade was that the Flames had a really good draft.

The 1973 1st the Habs immediately traded to move down in the draft to take Bob Gainey. That trade is very close to a win-win in terms of regular Point Shares, with the Habs just narrowly coming out on top. (Of course they actually won that one, as they got the one of the greatest defensive forwards of all time out of it.)

In the 1977 Draft, the Canadiens took Mark Napier, who had already been playing pro in the WHA but was eligible for some reason. Napier was excellent for the Canadiens in his six seasons, ranking 3rd in Goals (behind two Hall of Famers) over that span. He also contributed to their last Stanley Cup of the ’70s. They traded him to the North Stars in the Bobby Smith trade.

But the player they picked with the 1978 2nd never played in the NHL (and only even managed 4 games in the WHA).

The Seals pick was 2nd overall. (What does it say about the perceived quality of the 1973 Amateur Draft – the Denis Potvin Draft – that the Habs traded out of 2nd and then traded out of 5th?) With it, the Flames didn’t select the 2nd best player in the draft (that’s either Lanny McDonald or Rick Middleton) but they did select the 5th best player in the draft, Tom Lysiak. From the draft to 1979, Lysiak led all Flames in Goals, Assists and Points. (He has over 100 goals, over 90 assists and over 100 points more than his next teammate.) He also finished 2nd in Calder voting in his rookie year. He was traded to the Black Hawks at the 1979 Trade Deadline.

The other player the Flames took in the first round, at 16, was a bust. Vic Mercredi played two games for the Flames in 1974-75 and then headed to the WHA where he was just as successful.

But: What about the player who is 2nd on that list of Atlanta Flames scorers between 1973 and 1979? That’s Eric Vail, whom the Flames drafted in the 2nd round with the third of the picks in the trade. Vail lasted one more season, through the move to Calgary, and if you add that season, he’s first on the franchise in Goals, though he never caught Lysiak in points or assists. Vail also won the Calder a season after Lysiak finished 2nd. Vail was traded to the Red Wings in 1981.

Atlanta drafted their two best forwards of the first era of their existence with this trade.

7. Gary Bergman – (51.4) PS

Canadiens get nothing

Red Wings get: Gary Bergman – 55.4 PS (60G, 243A for 303P, +20 in 706 PS)

This is another cheat: Gary Bergman was waived in June 1963 and claimed by the Wings after bouncing around the Chicago and Montreal farm systems.

Bergman had hardly as impressive a career as some of the players on this list, but he played over 700 games for the Red Wings over more than a decade and helped the team to the 1966 Stanley Cup Finals, their last appearance for nearly 30 years. We don’t have ATOI to find out how much he played, but he did finish 6th in Norris voting one season. Bergman was traded to Minnesota in 1973.

6. Eddolls for Kennedy – (53) PS

Canadiens get: Frank Eddolls – 6.4 PS (5G, 9A for 14P in 57 GP)

Leafs get: Ted “Teeder” Kennedy – 59.4 PS (230G, 330A for 560P in 696 GP)

Teeder Kennedy was a junior hockey star in Port Colborne, Ontario. Even though he dreamed of playing for the Leafs, it was the Canadiens that first signed him, in 1942. However, the Habs bungled how they handled the teenager, failing to meet him when he arrived in Montreal, and didn’t seem to be fulfilling their promises to help him with his education, so he went home. You can read the full story about how the Canadiens alienated Kennedy and how Nels Stewart got the Leafs to acquire in September 1943 him, here.

The D the Leafs sent back, Frank Eddols, only played one full season with the Habs and then found himself too far down the depth chart once WWII ended. So he spent time in the AHL until he was traded to the Rangers in 1947. Eddols did help the Canadiens to the Stanley Cup in 1946 but he only ever played 57 regular season games for them.

Kennedy was an instant success in Toronto. In his age-17 season, he scored 25 goals. From 1943 until his retirement in 1957, he led all Leafs in Goals, Assists and Points, significantly outscoring his teammates. In 1951 he led the NHL in Assists. He made three All Star 2nd Teams and finished Top 5 in Hart voting three times through 1953. Controversially, in 1955, he was awarded the Hart. (We gave it to Beliveau.)

He and Leafs goalie Turk Broda were the first NHL players to win 5 Stanley Cups. He was part of the legendary Leafs four-peat in the late ’40s and Captain for the last of those. Despite rarely being among the top offensive players in the regular season, Kennedy led the 1945 playoffs in Goals, the 1949 playoffs in Assists, and the 1948 playoffs in Goals and Points. He is one of the best players in Leafs’ history.

The Eddols for Kennedy trade is also our 6th Best Maple Leafs Trade of All Time.

5. Savard for Chelios and a Pick – (65.7) PS

Canadiens get: Denis Savard – 14.5 PS (72G, 107A for 179P, +6 in 210 GP)

Blackhawks get:

• Chris Chelios – 80.2 PS (92G, 395A for 487P, +120 in 664 GP)
• 1991 2nd Round Pick (Mike Pomichter) – 0 PS (0 GP)

On June 29, 1990, the Habs traded franchise D Chris Chelios for Blackhawks star Denis Savard. Infamously, the Canadiens had chosen Regina’s Doug Wickenheiser over the homegrown Savard in the 1980 draft. Wickenheiser did not work out (see above) and some have viewed this trade as a belated attempt to correct the mistake.

Savard became the Blackhawks’ franchise player, scoring over 1000 points for them during the 1980s (4th most in the decade).

But, in the meantime the Canadiens had drafted and developed Chris Chelios, the 1989 Norris winner.

So, on its face, the trade was a star for a star, with Chelios only a year younger.

If you judge this trade solely by Cups, the Habs won, as Savard contributed to their 1993 Stanley Cup. However, Savard missed 6 playoff games, scored only 5 points, and was a -3. Could they have won it without him? Probably.

Judging the trade by regular season Point Shares, on the other had, turns the trade into a disaster.

Savard’s PPG plummeted immediately. For the Canadiens, Savard scored at nearly 40% less than the rate he scored for the Blackhawks. And management deemed him so valuable to the Stanley Cup-winning team they let him walk as a free agent in the off-season after he won his Cup.

The 2nd Rounder the Habs included in the deal to get Savard didn’t turn into an NHL player.

But Chris Chelios went on to win two more Norris trophies, both with the Blackhawks. In addition, he finished Top 5 in Norris voting a further three times, coming in 2nd to Paul Coffey in 1995 as well. While he was there, he led all Blackhawks skaters in Assists, and was 2nd in Points. In his final season for the Blackhawks, he was still playing over 26 minutes a game, despite being in his late 30s.

Though the Blackhawks never won a Cup, Chelios led the team to the Stanley Cup Finals in 1992, leading the playoffs in Plus/Minus, leading the team in assists and coming in 2nd on the team in points. (We have no idea how many minutes he played, but he likely played a lot.)

At the 1999 Trade Deadline, the Blackhawks traded Chelios the Red Wings, where he had more success and won two more Cups.

4. A pick and cash for 5 players – (68.4) PS

Canadiens get:

• 1973 2nd Round Pick (Glenn Goldup) – (0.6) PS (1A for 1P, -3 in 18 GP)
• Cash

Islanders get:

• Alex Campbell – 0 PS (0 GP)
• Denis DeJordy – 0 PS (0 GP)
• Tony Featherstone – 0 PS (0 GP)
• Glenn “Chico” Resch – 64.2 PS (157-69-47, 25 SO, .911 SV%, 2.56)
• Future Considerations (Germain Gagnon) – 3.6 Ps (20G, 43A for 63P, -15 in 125 GP)

Note: There is also a version of this trade which is just Resch for cash, which would make it slightly less bad than the Chelios deal, if that information is more accurate.

At least in this version, on June 6, 1972, the Canadiens traded a whole lot of stuff for a 2nd Rounder and cash. Hopefully it was a lot of money.

With that pick, the Habs drafted Glenn Goldup. He struggled to make the team and they traded him to the Kings in June 1976.

Alex Campbell was a teammate of Resch’s in the IHL, he would never play pro again after his 1972 season.

DeJordy had been a backup for the Habs the previous season, and he was traded by the Islanders to the Red Wings four months later.

Featherstone had been the Seals’ 1st Rounder in 1969 but had not been able to make the Habs. The Canadiens would reacquire him in December and trade him to Minnesota in 1973.

The player who the Islanders received as future considerations actually went on to play with them for a little bit. They traded him to the Black Hawks at the 1974 Trade Deadline.

But the reason this trade is on this list is due to Chico Resch. Resch had already excelled for his IHL team, winning two awards and making their All Star team. This wasn’t enough for the Canadiens, who already had goaltending. (After all, they sent out two goalies in this one transaction.)

He became the Islanders’ starter in 1974, after excelling in the Central Hockey League (winning their MVP). He finished 2nd in Calder voting that season, leading the league in Save Percentage and making the 2nd All Star Team. He led the league in Save Percentage a second time and again made a 2nd All Star Team. In his final season for the Islanders, he led the league in Shutouts.

Resch led the playoffs in Save Percentage for the 1974-75 Islanders, the first time the franchise made the Confederal Finals, losing in 7. (Resch out-played Parent this series, even though Parent was in the midst of a run as the best goalie in the world.) He won a Cup as a backup in 1980.

The Islanders traded Resch to the Rockies at the 1981 Trade Deadline.

3. Tomas Vokoun – (71.7 PS)

Canadiens get nothing

Nashville gets: Tomas Vokoun – 71.7 PS (161-159-46, 21 SO, .913 SV%, 2.55 GAA)

Cheating again, as Vokoun was left unprotected in the Predators expansion draft in 1998. But the Canadiens had drafted him, back in 1994. He had only ever played one game for the Habs in the 1996-97 season and had given up 4 goals. To be fair to the Canadiens, Vokoun’s AHL numbers were hardly specatular.

Vokoun became the Predators’ 1A immediately and became their starter in 2002. He made the All Star Game in 2004 and became one of the better goalies in the league for a crappy team. While with the Predators, Vokoun was Top 5 in Wins and Goalie Point Shares once and Top 5 in Shots Against, Saves and Save Percentage twice. In 2004, he led the playoffs in Save Percentage. The Predators traded Vokoun to Florida in 2007.

2. Recchi for Desjardins and LeClair – (132.9) Point Shares

Canadiens get: Mark Recchi – 33.2 PS (120G, 202A for 322P, +23 in 346 GP)

Flyers get:

• Eric Desjardins – 80.3 PS (93G, 303A for 396P, +143 in 738 GP)
• Gilbert Dionne – 0 PS (0G, 7A for 7P, -1 in 22 GP)
• John LeClair – 85.8 PS (333G, 310A for 643P, +197 in 649 GP)

On February 9, 1995, Rejean Houle made the worst trade of his tenure as Canadiens GM, when he traded Eric Esjardins and John LeClair and another player for Mark Recchi.

In fairness to the Habs, Mark Recchi was a star. He had already made three 2nd All Star Teams, and in the 1992-93 season, Recchi set the Flyers single-season record in points. There is a world in which this trade makes sense, in which Recchi puts up similar numbers to what he did on the Penguins and the Flyers, and the young D and the prospect don’t work out as well. But that is not the world we live in.

Recchi worked out well enough. From this trade until the trade that sent him back to the Flyers (see above), Recchi was 1st in Goals and Points, 2nd in Assists on the Canadiens. So it’s not like he was a bust.

Marcel Dionne’s brother Gilbert had put together some decent seasons for the Canadiens but was a disaster for the Flyers. He was released in the middle of the 1995-96 season.

Desjardins was only in his age-25 season and he had played a big role in the 1993 Cup run. He became the Flyers’ franchise D. He made the 2nd All Star team twice and finished Top 5 in Norris voting twice. In 1997 he helped the Flyers to the Stanley Cup Finals and, during the Flyers’ Conference Final run in 2000, he played 28 minutes per game. For his playoff career since the NHL tracked ice time, Desjardins averaged nearly 27 minutes per game.

LeClair hadn’t played as big a role in the 1993 Cup but is the same age as Desjardins. LeClair had even more acclaim on the Flyers, making four – count’em, four – 1st All Star Teams, including in the season of the trade, and three 2nd Teams. He scored 50 goals three seasons in a row and had at least 40 goals five seasons in a row.

In the Flyers 1997 run, LeClair was second on the Flyers in Points.

Desjardins retired as a Flyer. LeClair left as a free agent after the Lockout.

1. Tony Esposito – (176.5) Point Shares

Canadiens get: $25,000

Black Hawks get: Tony Esposito – 176.5 PS (418-302-148, 74 SO, .906 SV%, 2.93 GAA)

On June 11, 1969, the Black Hawks claimed Phil Esposito in the Intra-League draft.

So, we’re cheating yet again, as Esposito was waived and the Habs were awarded compensation. But Esposito played 13 games for the Canadiens so it’s not like they never had a chance to stick with him.

Of course, the Canadiens had too many goalies, including the rights to a certain young goalie attending US college at the time they waived Esposito.

But it’s still shocking that the Habs got nothing for a Hall of Fame goaltender who is, arguably, one of the top couple regular season goalies of all time.

Esposito has so many regular season accolades it’s hard to list them all. After he was claimed, Esposito

• Won the Calder
• Won three Vezinas (while it still the Jennings)
• Made three 1st All Star Teams
• Made two 2nd All Star Teams
• Led the league in Wins twice
• Led the league in Ties twice
• Led the league in Shots and Saves five times
• Led the league in Save Percentage twice
• Led the league in GAA once
• Set the single-season record in Shutouts
• Led the league in Shutouts three times
• Led the league in Minutes six times
• Led the league in Goals Saved Above Average three times
• Led the league in Goalie Point Shares twice.

Additionally, despite his reputation for being a playoff choker, Esposito led the 1971 playoffs in Save Percentage, GAA and Shutouts as he led the Black Hawks to within one win of the Cup. And he led the playoffs in shutouts two further times.

It’s worth remembering that the Canadiens received literally nothing in return for giving up Esposito.