Trades are hard. But they are not rare, and they do happen on occasion. The Montreal Canadiens have made several over their long history with every single team currently in the league at some point. What follows is a reverse chronological checklist of teams to come to a rather unsurprising conclusion as to which team the Canadiens have not traded with for the longest period of time.
Nashville Predators - June 29th, 2016
The Predators traded their captain Shea Weber to Montreal for P.K. Subban in a trade that has been widely analyzed, panned, critiqued, and explored in recent weeks. This wound is still fresh and stings every time it is brought up as Subban was an incredibly popular player in Montreal, which clouds unbiased judgment on this trade.
Chicago Blackhawks - June 24th, 2016
The Canadiens sent two second-round picks in the 2016 draft for Andrew Shaw to replace the freshly departed Lars Eller. It is certainly way too early to pass judgment on this trade, but definitely any Blackhawks fans who spoke about Shaw only spoke in glowing terms, so the Canadiens might have made a great trade to strengthen their immediate future at the expense of two highly viewed picks.
Washington Capitals - June 24th, 2016
The Canadiens acquired two second-round draft picks (one in 2017, one in 2018) for centre Lars Eller to bring a close to his tenure with the Canadiens. This trade obviously cannot be judged yet since the Canadiens haven't had a chance to use the picks they acquired, however Eller always felt like a black sheep on the team. Hopefully the Canadiens can use the picks to draft well for the future.
New Jersey Devils - February 29th, 2016
Devante Smith-Pelly was traded for Stefan Matteau. This was a trade of two disgruntled forwards who needed a new environment. In the weeks following the trade, Smith-Pelly was a top scorer for the Devils while Matteau continued to struggle in the NHL under different lights. The upcoming season will go to prove whether Smith-Pelly was a fluke in his end-of-season run with the Devils, and it will be a last chance season for Matteau in the NHL. This trade might end up being a wash, but currently leaning in the Devils favour.
Arizona Coyotes - January 15th, 2016
In a bizarre trade that still hasn't been fully explained, the Canadiens traded disappointing first-round pick Jarred Tinordi and minor-leaguer Stefan Fournier for Stefan Elliott and John Scott. Elliott was immediately flipped to Nashville for Victor Bartley, and both Bartley and Scott were promptly buried in the AHL.
Scott of course had heat with the league for winning a fan ballot for the All-Star Game, which some would point to as the reason for the trade. By the end of the season both Scott and Bartley left the Canadiens organization, while Tinordi was busted for PEDs. This entire trade remains a mess, and hard to pick a winner.
Anaheim Ducks - January 7th, 2016
The Canadiens traded third-string goalie Dustin Tokarski for forward Max Friberg after the acquisition of Ben Scrivens made Tokarski redundant. Friberg will be a veteran presence for the St. John's IceCaps this season while Tokarski hopes to recapture a backup spot in the Ducks organization. However with Bernier and Gibson ahead of him in the depth chart, he will probably find himself spending the season in the AHL.
Edmonton Oilers - December 28th 2015
Montreal traded troubled forward Zack Kassian for goaltender Ben Scrivens. Montreal was desperate to upgrade the backup goaltender position after Carey Price went down to injury and Tokarski was not up to the job to backup Mike Condon. Kassian made a few appearances in the NHL for the Oilers, but generally spent the year in the AHL. He will return with the Oilers next season. Scrivens left the Canadiens organization at the end of the year after failing in his task to boost the goaltending for the faltering team.
Vancouver Canucks - July 1st 2015
Canadiens traded popular forward Brandon Prust for Zack Kassian and a fifth-round pick in 2016 (which they used to draft Casey Staum). Neither team really was able to benefit from this trade as Kassian was suspended and went into a substance abuse program before the season even started, while Prust struggled to keep up with Canucks, and became a frequent scratch and injury recipient. He ended up being sent down to the AHL before being shut down for the rest of the season due to an injury.
Buffalo Sabres - March 2nd, 2015
Prospect Jack Nevins and a seventh-round pick in 2016 went to Buffalo for centre Torrey Mitchell, mere minutes after the Habs traded a fifth-round pick in 2016 for Brian Flynn. Buffalo was in full-on sell-off mode after an incredibly terrible season. Montreal was able to strengthen their fourth line quite substantially with the addition of these two players. Mitchell should continue as the pivot for the fourth line next season for the Canadiens.
Dallas Stars - November 11th, 2014
The Canadiens traded Travis Moen for veteran defenceman Sergei Gonchar. This was a shrewd trade by Marc Bergevin to unload Moen's two-year contract for an ageing veteran defenceman with one year remaining, who ended up playing a large role in mentoring Nathan Beaulieu.
Winnipeg Jets - October 5th, 2014
Backup goaltender Peter Budaj and Patrick Holland were traded for Eric Tangradi. Budaj has gone on to have a career renaissance as part of the Los Angeles organization, finishing as the best goalie in the AHL last season. Tangradi got a shot with the Canadiens, but was quickly sent down to the AHL and eventually left the organization.
Colorado Avalanche - June 30th, 2014
The Canadiens sent failed experiment Daniel Briere to Denver for P.A. Parenteau and a fifth-round pick in 2015 they used to draft Matthew Bradley. Essentially this trade was a then-current failed experiment for what would be a future failed experiment. Neither player managed in their stay to fit into Michel Therrien's desired play pattern, and ended up being discarded from the team as a result. The trade would be a wash if not for Parenteau getting bought out, and subsequently beginning to score goals for Toronto while the Canadiens struggled to find their offence.
New York Islanders - March 5th, 2014
A trade deadline acquisition of darling rental Thomas Vanek and a fifth-round pick in 2014 used to draft Nikolas Koberstein was made in exchange of Sebastien Collberg and a 2014 fifth-round selection. This might go down as one of Marc Bergevin's best trades, as Vanek instantly gave the Canadiens a scoring boost, and sent them into the playoffs on a high. Unfortunately he disappeared completely during the playoffs, and ended up not getting re-signed. In his time he provided excitement and energy to a depleted forward corps. Collberg never managed to establish himself in the NHL, and left for Europe.
Florida Panthers - March 4th, 2014
The Canadiens acquired Mike Weaver in exchange of a fifth-round pick in 2015. Weaver became shot-blocker extraordinaire during his two seasons with the club, replacing the departed Josh Gorges in that department. The addition of Weaver instantly made the bottom defensive pairing that much more difficult to score against.
Los Angeles Kings - April 22nd, 2013
Montreal sent a fifth round pick in 2013 for NHL depth defenceman Davis Drewiske. Drewiske played regular minutes for the remainder of the 2012-13 season, and even signed an extension at the end of the season, but found himself banished to the AHL for the remainder of his time in Montreal Canadiens organization. (Thanks to @donnieg1717 for pointing out this trade).
New York Rangers - March 23rd, 2013
Danny Kristo was sent to New York in return for Christian Thomas. This ended up being a trade of two prospects with a potential NHL upside, but neither managed to do much in their time with either team. Both are now resigned to AHL careers most likely, however Thomas may still surprise as part of the Capitals organization.
Tampa Bay Lightning - February 14th, 2013
Montreal exchanged goalies with Tampa Bay, shipping Cedrick Desjardins for Tokarski in a move that would prove to be very good for Bergevin. Desjardins never managed to establish himself in the NHL despite very strong AHL numbers. Meanwhile, Tokarski managed to take the backup job from Peter Budaj, and almost play hero in the 2014 playoffs when Carey Price went down to injury.
Calgary Flames - January 12th, 2012
Mike Cammalleri was pulled off of the bench during a regular-season game for the purpose of trade, along with goaltending prospect Karri Ramo and a fifth-round pick in 2012 for forward Rene Bourque, prospect Patrick Holland, and a second-round pick in 2013 (used to draft Zachary Fucale). This currently remains a terrible trade for the Canadiens who got rid Cammalleri out of spite, and did not shop him around at all by all accounts, picking up flash in the pan forward Rene Bourque. Aside from a short burst of productivity in the 2014 playoffs, Bourque was otherwise a salary cap anchor on the Canadiens.
Carolina Hurricanes - December 9th, 2011
The Canadiens take on the contract on disappointing defenceman Tomas Kaberle in return for ageing-yet-effective defenceman Jaroslav Spacek. The trade was immediately seen as a bad deal for the Canadiens, but general manager Pierre Gauthier insisted this was a good move to strengthen the Canadiens faltering power play, which he did by registering two assists in his first game with the Canadiens. It was all downhill from there. Kaberle struggled, was mostly a scratch the following season, and ended up getting a compliance buyout from the Canadiens by 2013.
Columbus Blue Jackets - July 7th, 2011
Montreal sent Ryan Russell to Columbus for Mike Blunden. Blunden ended up playing regular fourth-line minutes for the Canadiens that season, while Russell never managed to establish himself in the NHL and retired from professional hockey. A good depth move by the Canadiens.
St. Louis Blues - June 17th, 2010
2010 playoff hero Jaroslav Halak was traded to the Blues for Lars Eller and Ian Schultz in a very controversial move at the time. Halak appeared to be winning the starting job over Carey Price, so the trade came as a surprise, and the return was an additional shock as Eller was an unestablished forward, so expectations were much higher. The negative stigma was something that Eller never managed to shake during his entire Canadiens tenure.
Minnesota Wild - November 23rd, 2009
The Canadiens sent Guillaume Latendresse to Minnesota for Benoit Pouliot in a trade of two disappointments. Latendresse came to the Canadiens with a lot of fanfare, but perhaps his development was rushed to get him there, and his game was generally incomplete. Pouliot was a former first-round pick who had the tools for success, but couldn't put it all together. The fresh start for both was hoping to be the spark they needed to get their careers back on track. Latendresse went on a tear, scoring 25 goals for the Wild that year. Pouliot fell well below expectations, and compared to Latendresse's success was seen as a failure in Montreal.
Pittsburgh Penguins - June 27th, 2009
The Canadiens traded their sixth-round pick in 2010 for Pittsburgh's seventh-round pick in 2009 to draft goaltender Petteri Simila on the advice of their European scout who begged the team to draft the large imposing goaltender with the final pick. Unfortunately he didn't develop as hoped and never played a game for the Canadiens or their AHL farm team.
Toronto Maple Leafs - June 20th, 2008
Montreal dealt disgruntled forward Mikhail Grabovski for defenceman Greg Pateryn and Toronto's second-round pick in 2010, which the Canadiens then traded to Chicago for Robert Lang. It is unfortunate that the Canadiens gave up on the immature Grabovski so soon as he went on to carve quite the career for himself in the NHL with multiple seasons of 20+ goals. Pateryn is still establishing himself in the NHL and figures to be a bottom-pairing defenceman for the Canadiens this upcoming season.
Detroit Red Wings - February 8th, 2008
Prospect Francois Lemieux was traded to Detroit for forward Brett Engelhardt in a minor-league deal that had no real impact on either team in any way. Nothing to see here.
San Jose Sharks - February 25th, 2007
Montreal traded defenceman Craig Rivet and a fifth-round pick in 2008 (Julien Demers) for Josh Gorges and San Jose's first-round pick in 2007; a pick they used to grab Max Pacioretty. This is clearly an incredible trade for the Canadiens who managed to grab a top shot-blocking defenceman and a first-line forward for an ageing defenceman.
Philadelphia Flyers - June 24th, 2006
The Canadiens sent their 2006 third- and fourth-round picks for Philadelphia's third-round choice that the Habs used to draft Ryan White. White provided some top-notch trouble-causing minutes for the Canadiens, but his lack of discipline did not play well with new coach Michel Therrien, and White saw his way out of town as a free agent, ironically signing with the Flyers.
Ottawa Senators - June 24th, 2001
The Canadiens sent an eighth-round pick in the 2001 draft for forward Andreas Dackell. It was a good trade for Montreal as Dackell stayed with the Canadiens for three seasons, maintaining his career average pace of 30 points per season. When the 2004 lockout hit, Dackell returned to Europe and remained there for the remainder of his career.
Boston Bruins - February 21st, 2001
Montreal sent defenceman Eric Weinrich to Boston for defenceman Patrick Traverse. Weinrich played 22 games with the Bruins that season, then signed with the Flyers in the off-season. Meanwhile Traverse became a regular part of the Montreal Canadiens for the next two seasons, playing 65 games in 2002-03. By the following season he became an AHL regular and the Canadiens organization.
So there you have it. The Boston Bruins, our most hated blood rival ever, is the team that the Canadiens haven't traded with for the longest period of time. Can't say there is much surprise in this fact, come to think of it.