The report that Max Pacioretty will join the Leafs on a PTO sent shockwaves among Leafs fans.
It didn’t just have to do with the fact that the Leafs opted to bring in a veteran presence when some were hoping the younger players would get a proper chance, but also because Pacioretty was once a former captain of their forever rivals in the Canadiens.
It may shock you to wonder that this will not be the first time a player who once was a member of the Habs also got to suit up for the Blue and White during their career. Heck, it is not even the first time this calendar year that a player got to experience life on both sides of the rivalry, as Joel Edmundson was a member of the Leafs for a few months last season.
There have been 103 skaters and nine goalies throughout the history of the NHL who have played for both the Leafs and the Canadiens. Some spent more time in Montreal while others played more of their career in Toronto, but the fact of the matter is that a player taking part in both aspects of this historic rivalry is not uncommon.
What is surprising is learning of some of the players who got to play for both teams throughout their careers. Here are 10 of the more notable players that have done so.
Max Domi
It’s only fitting that we start off the list with one of the more recent players to switch over from Bleu Blanc et Rouge to the Blue and White. Max Domi was a player Leafs fans were hoping to one day make his way onto the team not just because of continuing the family tradition set by his father, Tie, but also because he was not shy in admitting he was a big fan of the team growing up.
That’s what made it devastating for the Toronto faithful when he got traded to the Canadiens in 2018 for Alex Galchenyuk and Domi fully embraced playing under the intense lights of Montreal. In fairness, he was incredibly productive in his two seasons there, including leading the team in scoring during the 2018-19 season with 72 points (which remains his career-high). After a rough regression the following year, he was traded that offseason to the Blue Jackets for Josh Anderson which began a three-year stretch where he kept bouncing between teams and was only able to get one-year deals.
This bouncing around came to an end when he signed with Toronto during the summer of 2023 and it didn’t take him long to make himself a fan favourite. By all accounts, he has embraced all that comes with being a Leaf which is why he decided to plant his roots and sign a four-year extension this summer.
Mikhail Grabovski
Originally selected by Montreal in the fifth round of the 2004 Draft, Mikhail Grabovski spent the first two seasons of his career with the Canadiens where he struggled to produce and never quite found his footing. That is because despite being a key contributor to the Hamilton Bulldogs (their AHL affiliate at the time) winning the 2007 Calder Cup, there was a disconnect between him and the team during his brief tenure there.
It came to a head when he left the Habs after being healthy scratched from a 2008 game against the Coyotes, which resulted in him being traded to the Leafs that summer in exchange for a second-round pick and Greg Pateryn. The move ended up being essential to kick-starting Grabovski’s career as he went on to have five productive seasons in Toronto, including the 2010-11 campaign where he was one-third of a successful line that included Nikolay Kulemin and Clarke MacArthur. When it came to facing off against the Habs, Grabovski always stepped up his game as he scored more points against them than any other team in the NHL.
While his Leafs tenure ended with a controversial buyout and public fallout, many fans in this city still look back on his tenure with the team fondly despite them occurring during challenging times.
Frank Mahovlich
It’s true, one of the all-time great Leafs who got his #27 retired spent his final three seasons in the NHL as a member of their biggest arch-rival.
Toronto fans now may remember Mahovlich as one of the key members of the last truly successful eras of the team as he helped them capture four Stanley Cups, including the most recent one in 1967. But people who were around the team during those days know that the relationship between him, the team, and the fans was not sunshine and rainbows. To make a long story short: Mahovlich had a rocky relationship with Punch Imlach stemming from a contract dispute after the 1962 season, was nearly sold to the Blackhawks before an All-Star game, and was often booed by the fans during his later years with the team.
After being part of a blockbuster trade with the Red Wings in 1968, Mahovlich spent parts of four seasons in Detroit before getting dealt in another big deal with the Canadiens in 1971. Those years in Montreal saw him capture two more Cups and a career year in 1921-72 where he finished with 96 points. The relationship between Mahovlich and the organization did improve well after his playing days ended, but one has to wonder how much different history would have been if things had been patched up sooner.
Tomas Plekanec
Tomas Plekanec is a legend among Canadiens fans because he was practically a lifelong Hab where he played just about all of his career in Montreal.
Never one of the top scorers in the NHL, Plekanec instead made a name for himself by being one of the top two-way centers in the league with smart plays at both ends of the ice and being one of the hardest workers on a nightly basis. He was also remarkably durable as there were very few instances where he was forced to miss some time with an injury and also could be relied on to finish in the top half of scoring for Montreal. Combine all of that with his signature turtleneck that he wore throughout his career and it’s no wonder he became a fan favourite during his 16 seasons there.
What doesn’t get brought up often is Plekanec’s brief tenure on the other side of the rivalry when he was traded to the Leafs at the 2018 deadline in exchange for Kerby Rychel, Rinat Valiev, and a second-round pick. The reason why it is a mere footnote is because his 17-game tenure was unremarkable with only two assists, though he doubled his point production in the playoffs with four points in seven games.
Vincent Damphousse
A rare instance where both Leafs and Canadiens fans have fond memories of a player who appeared on both sides of the rivalry, though it was Vincent Damphousse’s days in Montreal that are more revered.
Originally selected sixth overall by Toronto in the 1986 Draft, he was the most productive player to come out of that class with 1205 career points which is well ahead of Brain Leetch in second place. Damphousse took some time to get acclimated to the Leafs, but he ended up being one of their most dependable forwards offensively by the latter half of his tenure. With the team going nowhere, he would eventually get traded to the Oilers for a package that included Glenn Anderson and Grant Fuhr before getting dealt to his hometown team a year later.
The move to Montreal paid immediate dividends as Damphousse led the team in scoring with 97 points (his career high) and did the same in the 1993 playoffs with 23 points en route to the Habs capturing that year’s Stanley Cup. He would spend six more productive seasons there where he finished no worse than second in scoring before finishing up his career with the Sharks.
Tomas Kaberle
While he drove some fans nuts with his hesitance to shoot the puck, Tomas Kaberle was nonetheless one of the best defencemen the Leafs have ever drafted and developed in recent years.
Originally drafted in the eighth round of the 1996 Draft, Kaberle joined the Leafs full-time two years later and quickly became a staple on their blueline that lasted for parts of 12 seasons. There was rarely a time where he wasn’t the team’s leading scorer on the backend as he could be counted on to provide offence even as Toronto started their free fall after the lockout. To put into perspective how long he was part of the organization, his tenure started off when they were still playing at Maple Leaf Gardens and ended when Phil Kessel and Dion Phaneuf were leading the charge.
That conclusion came in 2011 when he was shipped to the Bruins in a contract year and helped Boston capture the Stanley Cup. Kaberle would sign a three-year contract with the Hurricanes that offseason but was quickly shipped to the Canadiens where he struggled to regain his form from the glory days. His final season in Montreal was in 2013 where he was a frequent healthy scratch and only appeared in 10 games before getting bought out so he could finish his career back in his native Czechia.
Shayne Corson
Shayne Corson was beloved by the Montreal faithful because he was an effective power forward for many years. He could do it all during his prime: hit, fight, score, and shut down the opposition, making him one of the biggest pests of his era.
Originally drafted eighth overall by the Canadiens in 1984, he ended up having two separate tenures with Montreal and ended up playing in 662 of his 1156 career games in Bleu Blanc et Rouge. Unfortunately for Corson, he suffered from ulcerative colitis throughout his career, which is a chronic digestive disorder that can cause severe pain and significant weight loss, and later panic attacks. Despite these challenges, he was able to power through them and even became a three-time All-Star.
After wrapping up his second tenure with the Habs in 2000, he signed with his hometown Leafs that summer where he spent the next three seasons of his career there. The most notable moment of Corson’s time in Toronto was when he got suspended for trying to kick the Islanders’ Eric Cairns after losing a fight in the dying minutes in Game 6 of the 2002 first-round series. Part of what brought him to the Leafs was getting to play alongside his brother-in-law: Darcy Tucker.
Darcy Tucker
He may be more known for his tenure with the Leafs, but Tucker began life in the NHL as a member of the Canadiens who selected him in the sixth round of the 1993 Draft.
Tucker got Habs fans excited that he could be the next-generation version of Corson because he too was a pest, which was put on display during his time in the WHL where he dominated as a member of the Kamloops Blazers. It caught the attention of the Montreal front office where they gave him an ELC and made him turn pro two years after drafting him. While he was electric with the AHL’s Fredericton Canadiens in his rookie season, the success never translated to the NHL during three lacklustre seasons where he struggled to find his footing.
The Habs grew impatient with his lack of progress so they traded him to the Lightning in 1998. This proved to be a big mistake as he started to improve during his two seasons in Tampa Bay before a trade to the Leafs in 2000 was where he truly found his footing. Although Islanders and Senators fans will tell you otherwise, Tucker was beloved during his eight years in Toronto where he could drive the opposition nuts with his antics and offensive abilities. It’s no wonder he remains a staple in the franchise well after his playing days ended.
Jacques Plante
The legendary Canadiens goalie who popularized the use of masks in the NHL and won six Cups in Montreal did indeed spend part of his career as a member of the Leafs.
Jacques Plante was certainly one of the top goalies of his era and a big part of why the Habs won five straight Cups from 1956 and 1960, but he was also an innovator of the sport. Apart from being the first goalie in league history to use a mask in a game, he was also the first to regularly play the puck outside his crease, the first to raise his arms to alert his defencemen of icing, and pioneered stickhandling the puck.
Plante was also among the first NHL players to successfully come out of retirement, doing so after two years away from the game. During the latter half of the second phase of his career, he was traded from the Blues to the Leafs where his first season in Toronto was arguably his best. In 1970-71, led the league with a .944 SV%, 1.89 GAA, and 52 goals saved above average while tying a franchise record with nine straight wins. That resulted in him earning second-team All-Star recognition and two more years with the Leafs before being dealt to the Bruins in 1973.
Kirk Muller
Should Pacioretty suit up in a game for the Leafs, he will be the third former Canadiens captain to suit up for the Leafs and the first since Kirk Muller when he spent two seasons in Toronto during the mid-’90s.
Taken one spot behind Mario Lemieux in 1984, Muller spent the first seven years of his career with the Devils where was among their top scorers the majority of the time. A 1991 trade to the Habs fell perfectly aligned with his prime, which included winning the 1993 Stanley Cup. As noted earlier, Damphousse led Montreal in playoff scoring that spring but right behind him in second was none other than Muller. Amazing how connected some of these players are eh?
Two years later, he began to bounce around the league which included a pit stop on his hometown Leafs. His offensive production in Toronto was not quite where it was during his prime and was soon dealt to the Panthers partway through his second season with the team. Muller was able to play six more seasons after that, including four with the Stars immediately after they hoisted the Cup in 1999.
Doug Gilmour
No such list is complete without mentioning the most notorious instance of a Leaf playing for their bitter rivals in Doug Gilmour.
He needs no introduction as far as the impact he made on the franchise during parts of seven seasons, but for those who don’t recall he was one of the fiercest competitors of his time. Acquired in the biggest trade in NHL history which involved ten players, Gilmour helped kickstart a renaissance era in the 90s as his 1992-93 remains the greatest single season a Leaf has ever had with 127 points. His legendary status was secured in the playoffs where he led the team in scoring with 35 points in 21 games played, including the double OT winner in Game 1 against the Blues. Later becoming captain, it was easy to see why he was one of the most beloved Leafs of that era apart from Wendal Clark.
He would bounce around the league after being traded by the Leafs to the Devils in 1997, which included a two-year stint with the Canadiens in the early 2000s. Gilmour had two fairly productive seasons in Montreal, with his lone full campaign seeing him finish fourth in scoring during the regular season and tied for first in the playoffs. He got traded back to the Leafs at the 2003 trade deadline but his return only lasted one game as he teared his ACL which prematurely ended his season and career.
Honourable Mentions: Joel Edmundson, Ron Hainsey, John Kordic, Mike Komiserak, Alex Galchekyuk,
