An introduction to the 25 Worst Trades in the modern history of the Montreal Canadiens
Earlier this year, I shared a list of the 25 Worst Trades in (modern) Toronto Maple Leafs history. It was a trip down memory lane; painful for Leafs fans, funny for Leafs haters. And I started thinking… what fans base would I most enjoy causing similar pain to? The Montreal Canadiens immediately sprang to mind. In all seriousness, my grandfather was a Habs fan, so I grew up liking them. But I switched to the Leafs when Grant Fuhr was traded to Toronto, and my choice of Toronto was solidified by Gilmour and Sundin. I had a blast doing the Leafs’ list, and the Canadiens were always #2 on my list thanks to the wealth of hockey history to work with.
While I was prepping this series, I was amazed the degree to which the Canadiens’ “dark” period of the late ‘90s and early ‘00s was directly associated with two waves of bad trades. The first wave robbed the team of its depth, and the second wave robbed the team of its stars. The Habs in the 80s were a powerhouse, making the Stanley Cup finals twice: they beat the Calgary Flames in 1986, and lost a rematch in 1989. Montreal was also consistently one of the best teams in the NHL during that decade. But they made some awful moves early in the 90s that started their downfall: four of the 10 Worst Trades occurred in an 18-month stretch between March 1990 and September 1991. After winning the Stanley Cup in 1993, the Habs began crumbling. This in turn led to a panic phase, resulting in three more deals from the “Top” 10 coming occurring during a 20-month period between February 1995 and October 1996. It speaks quite loudly to the Canadiens’ dynasty of the 1970s that just four of the 25 Worst Trades occurred during that decade (vs. 13 of them occurring during the 1990s). It is no wonder that the team fell from grace during the last half of the 90s.
As a Leafs fan, I freely acknowledge some jealousy of the Habs. Not just because of their success during the 70s and 80s, when the Leafs spiralled out of control: but because the Canadiens fans are fans. They aren’t corporate ticket holders who care more about being seen at the game than watching the action. They don’t tolerate losing and mismanagement, and they will stop going to games when their team doesn’t deserve their support. They also have no tolerance for players who fail to give a full effort on the ice, and they are far less guilty of falling in love with players who simply shouldn’t be part of the team’s core.
That being said, they have made some TRULY bone-headed moves, and this list is meant to “celebrate” some of their glorious missteps. But don’t worry; I also have plans to do a best-of list as well. In the meantime, this is the first in a series that will outline the 25 Worst Trades in Modern Montreal Canadiens history. I’ll quickly explain my methodology, and identifying a few trades that didn’t quite make the cut.
One core aspect of my list (compared to some others) is that I don’t put much stock in whomever the Canadiens’ trading partner chose with the draft pick(s) received. Fortunately for Canadiens fans, the Habs have traditionally been much more protective of their first-round picks than Toronto, avoiding a Tom-Kurvers-for-Scott-Niedermayer situation. But as an example, a Montreal trade with St. Louis in 1985 gave the Blues a third-round pick that they used on Nelson Emerson, who was a decent offensive forward during the 1990s. Now there is no guarantee that the Habs would have picked Emerson, so I would ignore him when determining whether the trade was bad or not. All that matters is the draft selection(s) made by the Canadiens’, because that is the only aspect of the deal they can control. So a deal can be a bust because the Canadiens squandered their draft choice, but a deal won’t necessarily be a bust simply because the other team hit a home run with their pick.
And with that, let’s get to a trade that surprisingly didn’t qualify for the Worst Of list, as well as a handful of honourable mentions.
Does Not Qualify: Montreal trades Sergio Momesso and Vincent Riendeau to the St. Louis Blues for Jocelyn Lemieux, Darrell May, and a 2nd Round Pick in 1989 (Patrice Brisebois) (August 9th, 1988)
This was a deal that I was absolutely certain would qualify as a terrible trade for Montreal. Darrell May was a minor-league goalie who never played for Montreal (or even again in the NHL after the trade). And Jocelyn Lemieux played just 35 games over two seasons for the Canadiens before being shipped to Chicago for a 3rd Round Pick (which became Charles Poulin, who never made the NHL).
Meanwhile, on the St. Louis side, things worked out fairly well. Sergio Momesso played 191 games over three seasons with the Blues, scoring 43 goals and 110 points to go along with 469 PIM. He was then shipped to Vancouver in one of the biggest trades in Canucks history: Momesso, Geoff Courtnall, Cliff Ronning, Robert Dirk and a fifth round pick (Brian Loney) for Dan Quinn and Garth Butcher. That trade almost single-handedly built up the core of the team that made the run to the finals in 1994. But despite how one-sided his departure was, Momesso still played well while he was in St. Louis and even chipped in 12 points in 22 playoff games. Vincent Riendeau played 122 games for the Blues in 3+ seasons, going 58-45-16 with four shutouts. He had a respectable 3.34 GAA, although his.883 save percentage was somewhat underwhelming. He was slightly better in the playoffs, but he lost more than he won (9-11, 3.27 GAA, .886 PCT). Riendeau was then dealt to Detroit for Rick Zombo. So the Blues got 313 regular season games from a pair of decent players, while the Habs didn’t get much in return. But I had forgotten that the Canadiens selected Patrice Brisebois with the 2nd round pick.
Including his a second two-year stint with the Habs to end his career, Brisebois played 896 games for the Montreal Canadiens (over sixteen seasons), which ranks him 11th all-time among Montreal players. He played more games than Doug Harvey, Steve Shutt, Jacques Lemaire and Saku Koivu. Those are some impressive names. He also ranks 28th all-time in assists and 35th all-time in points among Canadiens players. In his 14-year first stint (791 games) with the club, he had a positive +/- eight times, and was +10 or better three times. He was +10 overall despite a horrendous -31 in ’00-01 (a clear outlier for him). He scored 10+ goals four times, 20+ assists nine times, and 30+ points seven times. While not an overly physical player (typically getting 15-30 PIM), he had four seasons with 60+ PIM. He left for Colorado as a free agent, but two years later he was back and played a final 105 games as a Hab. Those are impressive numbers, and it’s a shame he wasn’t able to be a lifelong Canadiens player. But his long tenure and consistency (plus his 89 playoff games for the Habs) definitely makes this trade even at worst, and possibly even a modest win for the Canadiens.
Dis-Honourable Mention: Montreal trades Gilbert Delorme, Greg Paslawski and Doug Wickenheiser the St. Louis Blues for Perry Turnbull (December 21, 1983)
Perry Turnbull was a bust for the Habs. He lasted just half a season, scoring 13 points and posting a -12 rating in 40 games (along with 3 points in 9 playoff games). He was traded to the Winnipeg Jets for Lucien Deblois, who left for Quebec as a free agent after scoring 54 points in 112 games for Montreal. Not much of a return.
While the price paid wasn’t exactly astronomical, the Habs gave up a fairly useful player in Greg Paslawski. Paslawski had four seasons of 20+ goals and twice cleared 50 points, with a high of 29 goals and 64 points in ’86-87. He was also a hero in the Blues’ run to the Conference Finals in 1986, scoring 10 goals and 17 points in 17 games. After parts of six seasons with St. Louis he was flipped to the Winnipeg Jets in a deal for draft picks, one of which was sent to Boston for Steve Leach. Wickenheiser didn’t amount to much; his best output was 23 goals and 43 points in ’84-85. He played in parts of four seasons with the Blues before leaving via waivers. The last piece, Gilbert Delorme, played an uneventful year-and-a-half in St. Louis before being dealt to Quebec for Bruce Bell. The loss of the productive Paslawski makes this a bad trade, but not awful enough to make the worst-of list.
Dis-Honourable Mention: Montreal trades Dan Daoust to the Toronto Maple Leafs for a 3rd Round Pick in 1984 (later traded to the Minnesota North Stars, who selected Ken Hodge Jr.) (December 17, 1982)
Daoust was very productive for Toronto in his first three seasons, scoring 179 points in 205 games. He then settled into more of a defensive role, but he still played 518 games (of his 522 career total) as a Maple Leaf. He was a decent NHL forward on a bad team. The Habs flipped the draft pick to Montreal with Mark Napier and Keith Acton for Bobby Smith. Although a third-round pick itself isn’t worth 500+ games from a quality NHL player, this trade (similar to the Paslawski deal) was bad but not awful.
Dis-Honourable Mention: Montreal trades Donald Brashear to the Vancouver Canucks for Jassen Cullimore (November 13, 1996)
Donald Brashear was very early in his career when he was dealt to the Canucks, where he became something of a fan favourite. He played 388 games over six seasons. Not exactly an offensive dynamo, he only hit double-digits in goals once (11 in ’99-00), and only once cleared 20 points (28 in ’00-01). He only had one playoff appearance for the Canucks (four games in ’00-01), but he was a popular enforcer with an impressive 1,159 PIM. He cleared 200 PIM in each of his first three years in Vancouver, including a staggering 372 in ’97-98. Meanwhile, Jassen Cullimore was absolutely wasted in Montreal. After three appearances for the Canadiens in ’97-98, he was claimed by the Tampa Bay Lightning on waivers. He then played another 696 NHL games, with his final games coming in the 2010-11 season. He also won a Stanley Cup ring with Tampa Bay in 2004. To add insult to injury, Brashear played another 526 games post-Vancouver, meaning he played in 914 games after leaving Montreal. So the Canadiens lost out on both ends of the deal.
That’s all for now; click here to see the trades ranking #21-25 among the Worst Montreal Canadiens Trades in Modern History.