Sunday's trade that saw the Maple Leafs acquire forward Tomas Plekanec from the Canadiens in a four-player deal was the first between the teams in nearly a decade - and is only the third swap the franchises have made this century.
Here's a look at the five biggest trades between the franchises since the league's inception, listed in chronological order:
Maple Leafs acquire: G George Hainsworth
Canadiens acquire: G Lorne Chabot
Whens the last time you saw a good old-fashioned goalie swap? This one was monumental at the time, as it meant Hainsworth and Chabot were the first players in history to suit up for both the Leafs and Habs.
Hainsworth, who was 38 at the time, led the league in wins his first two seasons in Toronto; Chabot spent one season in Montreal before being traded to Chicago, where he promptly won the Vezina Trophy in 1935.
Maple Leafs acquire: F Ted Kennedy
Canadiens acquire: Rights to D Frank Eddolls
This is easily the most lopsided trade between the two teams. The Maple Leafs initially acquired the rights to Eddolls - a Quebec native playing in the Ontario Hockey Association at the time - in exchange for the rights to Joe Benoit in June 1940.
Toronto opted to return him to Montreal just over three years later - and in exchange, the Leafs got a future Hart Trophy winner and Hall of Fame forward who led the Maple Leafs to five Stanley Cup titles in the late 1940s and early 1950s. Eddolls spent three seasons with Montreal before being traded to the New York Rangers.
Maple Leafs acquire: F/D Greg Hubick
Canadiens acquire: F Doug Jarvis
The Leafs didn't know what they had in Jarvis, whom they drafted 24th overall in 1975 based on a resume that included a bronze medal at the World Junior Hockey Championship and OMJHL First-Team All-Star honors. Just over three weeks after selecting him, the Leafs traded him to the Canadiens for Hubick, who had spent the previous three seasons in the AHL.
While Hubick played just 74 games with Toronto, Jarvis made an immediate impact in Montreal - winning the Stanley Cup in each of his first four seasons with the team and not missing a game in seven years with the club. Jarvis, who was traded to Washington in a blockbuster deal in 1982, still holds the NHL record for consecutive regular-season games played (964).
Maple Leafs acquire: F John Kordic, sixth-round pick in 1989
Canadiens acquire: F Russ Courtnall
If you're a fan of a team whose general manager expresses a need to acquire toughness, be afraid. That's what Maple Leafs GM Gord Stellick said was the inspiration for this one-sided deal that saw the Leafs ship winger Courtnall to Montreal for noted rabble-rouser Kordic and a late-round pick.
Courtnall was a serviceable forward for the Canadiens in the late 1980s and early 1990s, scoring a career-high 76 points in 1990-91. Kordic did as he was asked - racking up 446 penalty minutes in 104 regular-season games - before being traded to Washington in 1991. He struggled with drug addiction and died of complications from an overdose in 1992 at age 27.
Grabovski, drafted 150th overall in 2004, couldn't crack the Montreal lineup as a regular. The Maple Leafs were more than willing to give him that opportunity, so they pulled the trigger on the teams' first deal in more than five years - in the middle of the league's free-agent frenzy, no less.
Grabovski was much-maligned during his time with the Leafs, but did produce three 20-goal campaigns over parts of five seasons in Toronto. Pateryn had just 13 points in 83 games over parts of four years with the Canadiens before he was traded to Dallas for Jordie Benn in February 2017.
(Photos courtesy: Getty Images)