- The Toronto Maple Leafs have made some of the biggest trades in NHL history.
- Wendel Clark for Mats Sundin is the most impactful trade in Leafs’ history.
- Doug Gilmour, Phil Kessel, and Rick Vaive were acquired via trade.
A big trade can reinvigorate a fanbase, reboot a franchise, and completely alter a team’s Stanley Cup odds.
For the Toronto Maple Leafs – a team with over 100 years of history – several trades have played a massive part in the ups and downs this franchise has endured.
Wendel Clark, Mats Sundin, Rick Vaive, and Tuukka Rask all feature on my list of the seven biggest trades in Maple Leafs’ history.
1. Wendel Clark, Sylvain Lefebvre, Landon Wilson, a First-Round Pick for Mats Sundin, Garth Butcher, Todd Warriner, and a First-Round Pick
This is a perfect example of why it’s tough to judge a trade right away.
It shocked the fan base when the Maple Leafs traded their beloved captain, Wendel Clark, to the Quebec Nordiques in 1994.
Clark, who was 27 at the time, was the heart and soul of the team, but general manager Cliff Fletcher worried that his physical play would catch up to him in his later years.
In a ruthless move, Fletcher sent Clark to Quebec for a package that included young centre Mats Sundin.
It was impossible to know at the time, but the Leafs were trading the current face of the franchise for a future one, as Sundin re-wrote the record book in Toronto and was named captain in 1997.
Clark returned to the Leafs via trade in 1997.
2. Gary Leeman, Alexander Godynyuk, Jeff Reese, Michel Petit, and Craig Berube for Doug Gilmour, Jamie Macoun, Ric Nattress, Kent Manderville, and Rick Wamsley
It’s not every day that teams pull off a 10-player swap, but this trade is all about one player: Doug Gilmour.
Gilmour was a star with the Calgary Flames and helped them win the 1989 Stanley Cup, but a bitter contract dispute ended in Gilmour requesting a trade midway through the 1991-1992 season.
The Maple Leafs jumped at the chance to acquire the Ontario native and pulled off what is now considered one of the most lopsided trades in NHL history.
Gilmour put up 127 points in his first full season with the Leafs and led the team within one game of their first Stanley Cup appearance since 1967.
Toronto retired the No. 93 in Gilmour’s honour.
3. Andrew Raycroft for Tuukka Rask
While the Gilmour trade greatly altered the Leafs’ trajectory in the right direction, this one did the opposite.
It’s hard to defend the trade all these years later, but the logic was straightforward when it was made. Toronto was searching for an immediate solution in goal and had two blue-chip prospects in net to offer: Justin Pogge and Tuukka Rask.
The Leafs’ brass thought that Pogge was the more promising prospect at the time, so they dealt Rask to Boston for Andrew Raycroft, who won the Calder Trophy in 2003-2004.
The rest, unfortunately, is history.
Not only did Raycroft struggle in Toronto, but Pogge never amounted to anything in the NHL, either. This led to a decade’s long search for stability in goal for Toronto.
Rask would go on to become an all-time great with the Bruins, and he regularly had some of the shortest hockey odds to win the Vezina Trophy during his tenure in Boston.
4. Dave “Tiger” Williams and Jerry Butler for Rick Vaive and Bill Derlago
The decision to move Dave “Tiger” Williams was not made easy. Williams was one of the most feared enforcers in the NHL at the time of the deal, and he also had some offensive chops.
But, just as with the Clark deal above, the Leafs ended up trading a current beloved player for a future one.
Vaive became the first player in franchise history to score 50 goals in a season, and his 54-goal campaign stood as the team record until Auston Matthews broke it in 2021-2022.
5. $8,000 for Turk Broda
You need to go all the way back to 1936 for this one, and it seems surreal now, but it’s not unfair to say that the $8,000 general manager Conn Smythe traded to Detroit for goaltender Turk Broda is the best bang-for-buck deal in team history.
Broda would lead the Maple Leafs to five Stanley Cups, and he won the Vezina Trophy twice.
6. Jacques Plante and a Third-Round Pick for a First-Round Pick (Ian Turnbull)
Jacques Plante is one of the best goaltenders in NHL history, but the Maple Leafs made the right decision when they sent him to Boston for a first-round pick in the 1973 draft.
The Leafs used that pick to draft Ian Turnbull, who spent the better part of the next decade playing alongside Borje Salming to form one of the best defensive pairs of that generation.
Turnbull’s 79 points in 1976-1977 still stands as the most by any Maple Leafs defenceman in a single season.
7. Kenny Jonsson, Darby Hendrickson, Sean Haggerty, and a First-Round Pick for Wendel Clark, Mathieu Schneider, and D.J. Smith
This is a painful one.
While reacquiring Clark was an emotional boost for the fan base, the first-round pick the Islanders landed turned into Roberto Luongo and Kenny Jonsson grew into a terrific two-way defenceman.