7 Biggest Trades in Montreal Canadiens History, Ranked

The Montreal Canadiens are the most successful team in the history of the National Hockey League. 

Montreal’s 24 Stanley Cups are an NHL record, and they are the only franchise with three dynasties, as recognized by the Hockey Hall of Fame.

The Habs have spent much of their history at the top of the Stanley Cup odds market, and to do so, they had to pull some shrewd moves.

Check out my list of the seven biggest trades in Canadiens history.

Biggest Montreal Canadiens Trades

1. 1970 First-Round Pick, Ernie Hicke, and Cash for 1971 First-Round Pick and Francois Lacombe   

Nobody could have known it at the time, but this trade ended up being one of the biggest coups in NHL history.

Montreal Canadiens general manager Sam Pollock made a cunning gamble by trading the Habs’ first-round pick in 1970 to the California Golden Seals for their first in 1971, banking that the Seals would struggle.

The gamble paid off, as the Golden Seals finished dead last.

That meant Montreal got to pick first overall, and the Habs used that pick to select Guy Lafleur.

Lafleur won five Stanley Cups with the Habs and holds the franchise record for most points (1,246). 

2. Paul Reid and Guy Allen for Ken Dryden and Alex Campbell

This is one of the most peculiar trades in NHL history.

The Boston Bruins selected Ken Dryden 14th overall in the 1964 NHL Amateur Draft, but they dealt his rights to Montreal days later. The trade went completely under the radar – so much so that Dryden didn’t find out he was actually drafted by the Bruins until the 1970s.

The results of the trade were the complete opposite.

By the time Dryden’s career ended, he had won the Calder Trophy, five Vezina Trophies, and six Stanley Cups.

3. Patrick Roy and Mike Keane for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko

One of the great trade sagas in NHL history, the Canadiens never really fully recovered from their decision to trade Patrick Roy to the Colorado Avalanche.

In their defence, Roy did request to be dealt because of a feud with Mario Tremblay, but the deal would become a turning point in team history.  

Roy led the Avalanche to two Stanley Cups and was a five-time All-Star, while the Habs haven’t won a championship since 1993.

4. P.K. Subban for Shea Weber

This trade serves as a reminder not to judge a deal – especially a big one – too quickly.

When the Canadiens announced they were trading P.K. Subban to the Nashville Predators for Shea Weber, the hockey world came down hard on the Habs.

Subban, 27 at the time of the deal, was one of the most exciting players in the NHL and endeared himself to Habs fans with his explosive style and personality.

Weber, 30, was an elite defensive defenceman, but had a lot of wear and tear on his body.

The deal would work out splendidly for both teams.

Subban helped the Predators reach their only Stanley Cup Final in 2017 and turned Nashville into a powerhouse that perennially sat near the top of the hockey odds in the Western Conference.

Weber, meanwhile, would enjoy a career resurgence with the Habs and was named the team’s captain in 2018.

Weber and the Canadiens went to the 2021 Stanley Cup Final. 

5. Chris Chelios and a Second-Round Pick for Denis Savard

This is one the Habs would like to have back.

Chris Chelios had established himself as one of the game’s best defencemen during his first five seasons in Montreal, but general manager Serge Savard was concerned about his off-ice behaviour and a knee injury.

Instead of being patient with Chelios, who won a Stanley Cup and a Norris Trophy with the Habs, Savard sent him to the Chicago Blackhawks for Denis Savard.

Savard was one of the best players in the league during his prime, but he was past his salad days and never really got going with the Habs.

Chelios, meanwhile, developed into one of the best defencemen in the history of the NHL and played until he was 48.

6. Garry Monahan and Doug Piper for Frank Mahovlich and Bart Crashley

Frank Mahovlich was a titan of the sport when he was dealt from Detroit to Montreal in 1971, but he proved he still had plenty of the tank with the Habs.

Mahovlich played the last four seasons of his career with Montreal and won two Stanley Cups.

None of the players that the Habs gave up for “The Big M” ever amounted to much in their NHL careers.

7. Max Pacioretty for Nick Suzuki, Tomas Tatar, and a Second-Round Pick

A masterclass in selling at the right time, general manager Marc Bergevin completely changed the course of the Canadiens with this deal.

Pacioretty was a terrific Hab and a strong captain, but the Habs knew the American winger’s days as a prolific scorer were numbered.

Thus, the Habs dealt Pacioretty to Vegas for a package centered around Nick Suzuki, who was named the youngest captain in franchise history in 2022.