As a Habs fan growing up in the 1990s, I was one of many that endured the dark era after the 1993 Stanley Cup victory. Over a span of just 2 years, gone were the likes of Patrick Roy, the trio of captains in Guy Carbonneau, Kirk Muller and Mike Keane, 1993 overtime legend John LeClair, Eric “hat-trick” Desjardins, amongst others. What many Canadiens’ fans witness after the last championship is an era in which many fans wished had never happened. The Rejean Houle years, as many would like to call it, however even during the latter end of Serge Savard’s and Bob Gainey’s tenure, there still remained trades where the Habs were clear losers. Here I look back at the top 10 worst trades that occurred after the 1993 Stanley Cup, a factor that has led to this Stanley Cup drought of over 2 decades.
10. Montreal Canadiens traded Guy Carbonneau to the St. Louis Blues for Jim Montgomery.
Okay, we all knew that Guy Carbonneau was past his prime and was no longer the shutdown forward the Canadiens had heavily relied upon in the 1993 Stanley Cup run. However, this trade was just the beginning of the end for the core players on that 1993 championship winning team. By trading their captain, just months after lifting the Stanley Cup, the Canadiens decided to go a different route that brought them to the promise land and demolished the leadership core of that cup winning team (Kirk Muller was traded months later). For a player nearing the end of his career, Carbo did play another 6 seasons, which included lifting another Stanley Cup in 2000 with the Dallas Stars. And the player the Habs got in return for their captain? Jim Montgomery, a player that only lasted 5 games with the Canadiens, posting up 0 points. In fact, Montgomery’s career lasted another 50 NHL games before retiring in 2003.
9. Montreal Canadiens traded Arron Asham and a 5th round selection (Markus Pahlsson) in 2002 to the New York Islanders for Mariusz Czerkawski.
Remember this? I sure did, I was probably one of many Habs fans jumping for joy on Draft Day 2002. We all thought we had ripped off the Islanders (hmm coincidence? we all thought we had ripped of the Islanders again acquiring Thomas Vanek this past trade deadline), acquiring a former back to back 30 goal scorer for a 4th line tough guy. In our defense, the Polish Prince was coming off 4 straight years where he had scored over 20 goals a season. Little did we know, Czerkawski was none existent in his 43 games as a Montreal Canadien. In the 43 games as a Hab, this former 30 goal scorer scored 5, yes that’s right 5 goals and 9 assists. Even though Asham has had his trouble with league suspension, he has been an ideal 4th line tough guy with some scoring capabilities for the Islanders, Flyers, Penguins, and more recently the Rangers. Do Habs fans still remember what Asham did to us in the 2010 Eastern Conference Finals while with the Flyers? Don’t underestimate the role of a grinder with some skill, Dale Weise anyone?
8. Montreal Canadiens traded Stephane Richer, Darcy Tucker and David Wilkie to the Tampa Bay Lightning for Patrick Poulin, Mick Vukota and Igor Ulanov.
Let’s just put it this way, I wouldn’t trade Darcy Tucker for all 3 of Poulin, Vukota, and Ulanov together. Tucker was a young, up and coming player who had only donned the Canadiens uniform for a combined 76 regular season games before being dealt. It was clear that GM Rejean Houle was building the Canadiens with size and the 5’10 Tucker was considered too small, but what he forgot was that you also need skill to win hockey games. Tucker went on to play another 12 effective seasons, with career highs of 61 points and 28 goals. Another blow to the Habs was that his best years were with arch rivals, the Toronto Maple Leafs. Richer had some average seasons in Tampa and St. Louis before retiring in 2002. Ulanov was a walking pylon on the backend for the Canadiens and was eventually dealt for Christian Laflamme. Poulin and Vukota, well let’s just say they were irrelevant for the Habs during their time.
7. Montreal Canadiens traded Trevor Linden, Dainius Zubrus and a 2nd round selection in 2001 to the Washington Capitals for Richard Zednik, Jan Bulis and a 1st round selection in 2001.
You might think I’m crazy for listing this trade so high, but when you think about it, the Canadiens traded away the two key characteristics they have been missing for years, depth and size at the centre position. Sure, Zednik provided the Canadiens with some goal scoring, especially the two goals in Game 7 vs. the Bruins in the 2004 playoffs. And Bulis had his moments, like the 4 goal night in Philadelphia. However, Linden and Zubrus were the last two decent centres with considerable size that the Canadiens have had since. You can definitely argue that Linden’s best days were over, as he was plague with injuries in his 2 seasons with the Habs. But after leaving Montreal, Linden went on to play another 7 seasons, averaging around 40 points and bringing leadership intangibles to both the Capitals and Canucks. Zubrus, who is still playing as of today, has had a long and solid career with decent seasons in both Washington and New Jersey. Comparable to today, the Canadiens trading a 22- year old Dainius Zubrus at the time would be like trading away Lars Eller, whose career best will probably average at best 40-50 points, just like Zubrus.
6. Montreal Canadiens traded Vincent Damphousse to the San Jose Sharks for 5th round selection in 1999, 2nd round selection in 2001 and a 1st round selection in 2000.
On paper this looks like a decent trade for an impending Free-Agent, acquiring a first and a second round draft pick is crucial for any rebuilding team, as were the Canadiens at the turn of the century. However, it was known at the time that then captain Vincent Damphousse, the last of 2 players (Brunet) remaining from the 1993 Stanley Cup team wanted to resign and retire in a Habs uniform. What the Habs failed to realize and evaluate was what Vinny had left in the tank. Many in management and fans alike, all thought Damphousse best years were behind him. However, after being acquired by the Sharks, Damphousse went on to score 70 points in 82 games the following year. As a matter of fact, Damphousse went on to have another 6 successful seasons as a member of the San Jose Sharks, including playoff runs in 2001-02 and 2003-04. The second round pick the Habs received? They traded it away to Columbus for skipping on goaltender Mathieu Garon in the Expansion Draft. And the first round pick? Marcel Hossa, the brother of Marian, who was the epitome of first round draft bust during the Houle regime.
5. Montreal Canadiens traded Pierre Turgeon, Rory Fitzpatrick and Craig Conroy to the St. Louis Blues for Murray Baron, Shayne Corson and 5th round selection (Gennady Razin) in 1997.
Till this day, no one knows what more Pierre Turgeon could have done to avoid being the fifth straight Canadiens’ captain to be traded (Chelios, Carbonneau, Muller, Keane). Turgeon, who was recently acquired from the Islanders for Captain Kirk Muller, was the newly appointed captain of the Canadiens after Mike Keane was traded to Colorado. In his only full season with the Canadiens in 1995-96, Turgeon put up 38 goals and 58 assists for 96 points in 80 games. Can you remember the last Canadiens to score over 90 points? 10 games into the following season, GM Rejean Houle decided to trade his captain to St. Louis for former Canadiens’ fan favourite Shayne Corson. Corson was a rugged grinding forward that was love by the fans, however it was crystal clear his best seasons were behind him. His four seasons in Montreal were filled with injuries, with his best season scoring 55 points. One for one the trade already looks bad for the Canadiens, however when you factor in that the Habs also threw in Craig Conroy, a solid two-way centreman, with seasons of 75 and 66 points, this trade definitely enters the top 5 worst trade since the last Stanley Cup.
4. Montreal Canadiens traded Mike Ribeiro and a 6th round draft selection in 2008 to the Dallas Stars for Janne Niinimaa and a 5th round draft selection in 2007.
What were they thinking? For years, the Canadiens were looking for depth down the middle, a centreman that could carry them, let alone a French Canadian. They had one in Mike Ribeiro, a young playmaking centre from Montreal, Quebec, who in his first 2 full NHL seasons with the Habs put up 65 and 51 points. Then just before the start of the 2006-07 regular season, the Canadiens suddenly decided to deal Ribeiro and his off-ice antics to Dallas for Janne Niinimaa. That’s right, Janne Niinimaa, an over his prime, even if he had a prime, Janne Niinimaa. Niinimaa only lasted half a season with the Canadiens before ending his NHL career and leaving for the Swiss league. Meanwhile, Ribeiro had 6 great seasons with the Stars in which he netted years with 78, 83 and 71 points. The loss of Ribeiro left a hole down the middle for the Canadiens, in which they went searching for a replacement. Let me introduce, Scott Gomez…
3. Montreal Canadiens traded Christopher Higgins, Ryan McDonagh, Doug Janik and Pavel Valentenko to the New York Rangers traded Scott Gomez, Tom Pyatt and Mike Busto.
The trade the marked the end of the Bob Gainey era. It is still a mystery to Habs fans, as to why Gainey decided to target the overpaid 7.3 million Scott Gomez instead of just resigning team captain and fan favourite, Saku Koivu. It was evidently clear across the league that Gomez was overpaid and was on the downhill of his NHL career. There were even rumblings that the Rangers were willing to give up draft picks to any team willing to take on Scott Gomez’ atrocious contract. In comes, Santa Claus, I mean Bob Gainey. Not only did the Canadiens’ give up then assistant captain Chris Higgins, who two years before put up 27 goals, but they also gave up future NHL stud defensemen Ryan McDonagh, a top 10 draft pick in the 2007 NHL Entry Draft. McDonagh has since become a top 10 defensemen in the NHL and a crucial part to the Rangers’ Stanley Cup run in 2012 and 2014. McDonagh was also a top pair defenseman for the USA at the 2014 Olympic Games. What made matters worse was that McDonagh played an important role in eliminating the Canadiens in the 2014 Eastern Conference Finals, scoring 2 goals and 8 assists as the Rangers knocked off the Habs in 6. Fans to this day still ponder what if McDonagh and Subban had played together. Oh and I almost forgot, Scott Gomez went 60 games without a goal and was eventually bought out by the Canadiens just before the 2013 season.
2. Montreal Canadiens traded Eric Desjardins, Gilbert Dionne and John LeClair to the Philadelphia Flyers for Mark Recchi and 3rd round selection in 1995.
Following the disaster of the shortened season of 1995, where the Canadiens failed to make the playoffs for the first time in 25 years, GM Serge Savard was in dire need to shake things up. When the Flyers’ made then-star winger Mark Recchi available, Savard pulled the trigger. Yes, Recchi did have some decent years in a Canadiens’ uniform, notching back to back 30 goals. However, the Habs gave up perennial 50 goal scorer and future All-Star John LeClair, who with Eric Lindros, became the deadliest duo in the NHL at the time. Not only that, but they also managed to trade defenseman Eric Desjardins, who became the Flyers’ top defenseman for a decade, while also making the Canadian Olympic Team at the 1998 Nagano Games. In a blink of an eye, the Canadiens traded away 2 heroes from the 1993 Stanley Cup run, John LeClair, who scored 2 overtime goals in Games 3 and 4 against the Kings and Eric Desjardins, who scored a hat-trick including the game winning goal in Game 2.
1. Montreal Canadiens traded Patrick Roy and Mike Keane to the Colorado Avalanche for Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault.
Oh yes, the trade of Saint Patrick. How can any Montreal Canadiens’ fan forget the eventful night of December 2, 1995. In a game against the Detroit Red Wings, Roy allowed 9 goals in just 26 shots and was rudely mocked by both recently hired Coach Mario Tremblay and the fans at the forum. After finally getting pulled midway through the 2nd period, Roy walked passed Tremblay, straight to team president Ronald Corey, and declared “It’s my last game in Montreal.” Four days later, newly appointed GM Rejean Houle traded future Hall of Famer Patrick Roy, along with then team captain Mike Keane to the Colorado Avalanche for young netminder Jocelyn Thibault and forwards Martin Rucinsky and Andrei Kovalenko. Roy and Keane played crucial roles in the Avalanche’ Stanley Cup victory just mere 6 months later. Kovalenko only lasted a season in Montreal before being traded to Dallas for grinder Scott Thornton. Rucinsky provided the Habs with some quality years as a 20-goal scorer, however was invisible in the playoffs. And Thibault, after some rocky years with the Habs, never reached his potential as the next great French Canadian goaltender, and was eventually dealt to Chicago with Dave Manson for Jeff Hackett and Eric Weinrich. Oh yeah, Patrick also led the Avalanche to another cup in 2001 and became the winningest goalie in the playoffs.