When talking about longstanding rivalries in the NHL, it’s hard to ignore the Montreal Canadiens’ beef with the Philadelphia Flyers. While every day heated contests between the teams haven’t really occurred in recent years, it’s the postseason matchups that have sparked legendary moments for both clubs. The Canadiens swept the Flyers in the 1976 Stanley Cup Final to deny Philadelphia of their third straight Cup victory. The Flyers would later get some revenge during game six of the 1987 Eastern Conference Final with the infamous “Brawl in Montreal” where the Flyers would eliminate the Habs, and again beating them in the 2010 playoffs in what was considered a huge upset.
Off the ice, their relationship was equally as hot and cold, sometimes being great partners with many trades, and other times going decades without making a deal.
6/12/69 – Jean-Guy Gendron for cash
Jean-Guy Gendron was a longtime forward who had spent the previous three seasons with the Quebec Aces of the AHL, a team the Flyers would later purchase as their farm team in 1967. He was acquired by the Flyers organization in that move, but later lost to the Montreal Canadiens during the 1969 Intra-League Draft. The following day, he was traded back to the Flyers in this deal for cash considerations. Gendron would play four seasons with the Flyers before heading to the World Hockey Association in 1972.
10/30/86 – Dom Campedelli for Andre Villeneuve
Their second trade was the first between the two clubs in over 17 years.
This deal was a swap of depth players. Dom Campedelli was a defense prospect who played two games with the Canadiens during the 1985-86 season. Upon his arrival in the Flyers’ organization, he’d play the remainder of the 1986-87 season with the Hersey Bears before leaving the franchise during the offseason. He’s spend two more seasons in the AHL before retiring in 1988.
Andre Villeneuve was a defenseman who played a season-and-a-half with the Hershey Bears. He had two relatively unsuccessful seasons with the Canadiens’ minor league team before also retiring in 1988.
11/7/88 – Scott Sandelin for J.J. Daigneault
Scott Dandelin is best known for his 20+ year tenure as head coach of the NCAA’s Minnesota-Duluth Bulldogs, but he had a short, injury-riddled professional career before stepping behind the bench.
He was Montreal’s second round pick in 1982 and played nine games with the team from 1986 to 1988. He was acquired by the Flyers where he’d play 15 NHL games in 1990-91 before leaving in free agency that summer and joining his hometown Minnesota North Stars for one season before retiring.
J.J. Daigneault was a journeyman defenseman who played a season-and-a-half with the Flyers, making the Canadiens the third team he suited up for in his five-year career when Montreal acquired him. By far his longest tenure came with the Canadiens where he’d play 352 games over the course of seven seasons. He was a key member of their Stanley Cup winning team in 1993.
3/5/91 – Mark Pederson for 1991 second round pick (Jim Campbell)
Mark Pederson was the Canadiens’ 15th overall pick in 1986. He played 56 games for the club over the course of a season-and-a-half before this trade occured. He’d play parts of three seasons in Philly, with the 191-92 season being the only full campaign. He scored 50 points in 82 games as a Flyer before being traded to the Sharks just before Christmas in 1992.
The Canadiens drafted forward Jim Campbell 28th overall in 1991. He played three seasons with their AHL squad before being traded to the Anaheim Mighty Ducks in 1996.
11/28/93 – Ron Ramage for cash
Ramage was a 14-year NHL veteran upon his arrival to Philadelphia in this trade. He had only played 14 games with the Canadiens over the prior two seasons and he’d only play 15 games with one assist for the Flyers before hanging up the skates during the 1994 offseason.
2/21/94 – Frederic Chabot for futures
Frederic Chabot was a goaltending prospect that played five games in Montreal from 1990 to 1994. He was acquired by the Flyers and played four games in Philly during the remainder of the 1993-94 season and left for the Florida Panthers during free agency in 1994.
6/29/94 – Kevin Haller for Yves Racine
Haller was a defenseman who had five NHL seasons under his belt upon his arrival to Philly. He played parts of three seasons with the Flyers. He is probably best remembered as part of the trade that brought Paul Coffey to Philadelphia in December of 1996.
Yves Racine, a defenseman, played 72 games for the Canadiens over the following two seasons. He was claimed off waivers by the San Jose Sharks in Janurary of 1996.
2/9/95 – Eric Desjardins, John LeClair and Gilbert Dionne for Mark Recchi and 1995 third round pick (Martin Hohenberger)
This deal ended up being one of the best trades in franchise history for the Flyers. Both teams had slow starts to the seasons and considered this trade as a shakeup, addressing the needs for both as the Flyers needed help on defense and the Habs wanted a high-powered forward.
Eric Desjardins quickly rose to the top of the defensive depth chart for the Flyers, playing as their number one defenseman for 11 years, serving as captain for parts of three seasons.
John LeClair stepped up in a big way upon his arrival in Philadelphia when he was placed on a line with Eric Lindros and Mikael Renberg and the Legion of Doom was born. He’d play 10 seasons in Philly, eclipsing the 50-goal plateau three times, and touching 40 an additional two times.
Gilbert Dionne was a depth winger who only played 22 games for the Flyers over the following two seasons. He signed with the Florida Panthers in 1996.
Mark Recchi would play four seasons with the Habs, but never quite reached of offensive totals he had with Pittsburgh and Philadelphia earlier in his career. He was traded back to the Flyers in 1999.
The Canadiens used their third round pick on forward Martin Hohenberger, but he’d never play a game in the NHL, suiting up for just nine AHL contests with Montreal’s AHL club in 1998.
2/10/95 – cash for Mark Lamb
Mark Lamb was a longtime NHL center who had won a Cup with Edmonton in 1990. He was acquired by the Flyers at the 1994 trade deadline and dealt away in this trade after missing most of the 1994-95 season with injuries. He’d play 39 games with Montreal for the remainder of the 1994-95 season and a single game in 1995-96 before leaving for the International Hockey League for four seasons before retiring.
3/10/99 – Mark Recchi for Dainius Zubrus, 1999 second round pick (Matt Carkner) and 2000 sixth round pick (Scott Selig)
Just over four years after Recchi was traded to Montreal, the Canadiens traded him back to Philly.
Dainius Zubrus was a former 15th overall pick in 1996 but struggled to establish himself in the Flyers’ lineup for three seasons before this trade. He found greater success with the Habs but was flipped to the Capitals at the 2001 trade deadline.
The Canadiens drafted defenseman Matt Carkner 58th overall in 1999, but he never signed with the club. He’d eventually go on to play 237 NHL games, most notably with the Ottawa Senators.
Scott Selig was a forward who was playing at Northeastern University when he was drafted 172nd overall in 2000. He played just 33 ECHL games before retiring in 2005.
Mark Recchi, who was now 11 years into his career, returned to Philly to slightly less production than he had years before, but nevertheless, was still one of their top scorers for an additional five seasons. Through both of his tenures in Philly, he’d score 627 points in 602 games.
10/20/99 – futures for Karl Dykhuis
Karl Dykhuis’ second stint in Philly came to a premature close when their blue line got crowded. He was shipped to the Tampa Bay Lightning in August of 1997 and reacquired from the Bolts in December of 1998. The Flyers had signed 15-year NHL veteran Ulf Samuelsson to a contract in what would become his last professional season. Because of it, they dealt Dykhuis to the Canadiens for future considerations after just 50 games less than 10 months later.
12/7/00 – P.J. Stock and 2001 sixth round pick (Dennis Seidenberg) for Gino Odjick
Stock started the 2000-01 season with the Canadiens after signing with them as a free agent the same summer. He played just 20 games in Montreal when they acquired enforcer Gino Odjick in this trade.
Odjick played parts of two seasons for the Canadiens, but would miss the entire 2002-03 season dealing with a concussion and was later suspended for failure to report to Montreal’s AHL squad. He retired from hockey shorty after.
Stock would finish out the 2000-01 season in Philly but would leave the team in free agency, signing with the New York Rangers and would be claimed by the Boston Bruins on waivers before the start of the 2001-02 season.
The Flyers drafted defenseman Dennis Seidenberg with the 172nd pick in the 2001 draft. He played parts of three seasons with the Flyers and Phantoms before a trade sent him to the Phoenix Coyotes in early 2006 in exchange for Petr Nedved.
1/29/03 – Eric Chouinard for 2003 second round pick (Max Lapierre)
Chouinard was the 16th overall pick in 1998 and struggled to carve out a spot in the NHL, only playing 13 games for the Canadiens during his four seasons with the club. He was acquired by the Flyers before the 2003 NHL trade deadline and would only play 45 games with them before he was traded the Minnesota Wild in December of 2003.
The Canadiens drafted forward Max Lapierre, who played six seasons with the team, racking up 40 goals and 284 penalty minutes in 293 games.
6/24/06 – 2006 third round pick (Jon Matsumoto) and 2006 fourth round pick (Jakub Kovar) for 2006 third round pick (Ryan White)
This trade happened so the Canadiens could move up 13 spots in the third round of the 2006 draft to select forward Ryan White. He would be apart of the Canadiens organization until 2014. He split his time between the AHL and NHL, typically serving as an enforcer during his career.
In exchange, the Flyers acquired selections number 79 and 109 in the third and fourth round respectively.
They drafted forward Jon Matsumoto, who spent four seasons playing for the Phantoms but never made it to the NHL while in the Flyers’ system, as well as Czech goaltender Jakob Kovar, though he returned to Europe shortly after his career in the CHL came to an end.
6/24/17 – 2018 seventh round pick (Brett Stapley) for 2017 seventh round pick (Cayden Primeau)
Eleven years after their last trade, the Flyers and Canadiens came together once again, this time to swap seventh round picks in a move that would become a running tradition over the following few seasons. The Habs drafted goaltender Cayden Primeau, who is the son of former Flyers captain Keith Primeau.
The Flyers would later trade the 2018 seventh back to Montreal.
6/23/18 – 2019 seventh round pick (Rafeal Harvey-Pinard) for 2018 seventh round pick (Brett Stapley)
A year later at the 2018 entry draft, the Flyers traded back the 2018 seventh round pick they acquired the previous year in exchange for a 2019 seventh round pick.
The Canadiens drafted forward Brett Stapley, who was a standout star for the University of Denver, where he won a national championship in 2022.
The Flyers would once again trade the 2019 seventh round pick back to the Canadiens.
2/9/19 – Byron Froese and David Schlemko for Dale Weise and Christian Folin
One of the first moves Chuck Fletcher made as Flyers’ GM was undoing some Ron Hextall-era nonsense. He traded Dale Weise, who was in the last year of his contract, and defenseman Christian Folin to Monreal in exchange for depth forward Byron Froese and defenseman David Schlemko.
Froese finished out the season with the Lehigh Valley Phantoms and left in the 2019 free agency.
David Schlemko was bought out of the last year of his $2.1 million contract during the 2019 offseason. The team paid him $600,000 for two seasons.
Weise split the following season between the Habs and AHL Laval and didn’t re-sign with the club in 2020.
Christian Folin signed a one-year extension with the Canadiens for the 2019-20 season, but he as well would split time between the NHL and AHL.
7/22/19 – 2020 seventh round pick (Traded to NSH) for 2019 seventh round pick (Rafeal Harvey-Pinard)
In the finale of their series of trading seventh round picks, the Flyers acquired a 2020 seventh round pick in exchange for a seventh round pick in 2019.
The Flyers would later package this pick along with their own 2020 seventh round pick to Nashville in exchange for a 2020 fifth round pick they’d use to select forward Elliot Desnoyers.
The Canadiens drafted forward Rafael Harvey-Pinard 201st overall in 2019. He currently plays for their AHL team the Laval Rocket.
2/24/20 – Nate Thompson for 2021 fifth round pick (Daniil Sobolev)
One of two depth additions the Flyers made at the 2020 trade deadline was acquiring Nate Thompson for a fifth round pick in 2021. Thompson finished the campaign with the Flyers, and would later re-sign with the team for the 2021-22 season after spending a year in Winnipeg.
The Canadiens drafted defenseman Daniil Sobolev 141st overall in 2020.
4/7/21 – 2022 seventh round pick (Miguel Tourigny) for Erik Gustafsson
During the 2020 offseason, the lone noteworthy move the Flyers made was signing free agent defenseman Erik Gustafsson to a one-year, $3 million contract. He produced one goal and 10 points in 24 games and was dealt to the Canadiens at the trade deadline for a 2022 seventh round pick. Gustafsson played 16 postseason games for the Canadiens as they advanced all the way to the Stanley Cup Final but ultimately lost to the Lightning in five games.
The Flyers traded the seventh round pick to the Coyotes as part of the cap dump of Shayne Gostisbehere in the 2021 offseason.
By: Dan Esche (@DanTheFlyeraFan)
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