10 Worst Trades For Toronto Maple Leafs Over the Past 45 Years

10 Worst Trades For Toronto Maple Leafs Over the Past 45 Years

By Darrell Samuels

July 21, 2015

10 Worst Trades For Toronto Maple Leafs Over the Past 45 Years

Dave Keon, Toronto Maple Leafs — Since 1967, the Toronto Maple Leafs have a history of making unsuccessful trades. The Leafs have lost some of their best players or prospects in trades, with little in return. Toronto fans have been upset about some of these trades for years. These 10 trades have caused nothing but agony to those watching faithfully over the past half century.

Since 1967, the Toronto Maple Leafs have a history of making unsuccessful trades. The Leafs have lost some of their best players or prospects in trades, with little in return. Toronto fans have been upset about some of these trades for years. These 10 trades have caused nothing but agony to those watching faithfully over the past half century.

10. Alyn McCauley, Brad Boyes and 2003 First-Round Pick (later traded to Boston, who selected Mark Stuart) to San Jose Sharks for Owen Nolan (Mar. 5, 2003)

Alyn McCauley, San Jose Sharks — This was a terrible deal for the Toronto Maple Leafs. Former Leafs GM John Ferguson Jr. rocked the boat and dealt to try and win now by giving up on prospects. Well, that didn’t work! Over 86 games in Toronto, McCauley had 62 points and a series of injuries to boot. He played in 201 career games in San Jose, accumulating 89 points, while Boyes developed in San Jose and is still playing in the league.

This was a terrible deal for the Toronto Maple Leafs. Former Leafs GM John Ferguson Jr. rocked the boat and dealt to try and win now by giving up on prospects. Well, that didn’t work! Over 86 games in Toronto, McCauley had 62 points and a series of injuries to boot. He played in 201 career games in San Jose, accumulating 89 points, while Boyes developed in San Jose and is still playing in the league.

9. Kenny Jonsson, Sean Haggerty, Darby Hendrickson and First-Round Pick in 1997 (turned out to be goaltender Roberto Luongo) to New York Islanders for Wendel Clark, Mathieu Schneider and D.J. Smith on (Mar. 13, 1996)

Roberto Luongo, New York Islanders — Wendel Clark was beloved. There were a lot of upset fans when he was traded for Mats Sundin in June of 1994. This trade was horrible for the team as the first-round pick resulted in parting with Roberto Luongo, and he became one of the league’s top goaltenders. The other players in this trade were either at the end of their careers or didn’t have much value. Trading the draft pick was a mistake by Leafs management.

Wendel Clark was beloved. There were a lot of upset fans when he was traded for Mats Sundin in June of 1994. This trade was horrible for the team as the first-round pick resulted in parting with Roberto Luongo, and he became one of the league’s top goaltenders. The other players in this trade were either at the end of their careers or didn’t have much value. Trading the draft pick was a mistake by Leafs management.

8. Two First-Round Draft Picks and Second-Round Pick to Boston Bruins for Phil Kessel (Sept. 18, 2009)

Tyler Seguin, Boston Bruins — This might be considered a deal that should have been a winner for Toronto. However, they struggled terribly over two years while Boston was acquiring the Leafs’ picks. It resulted in Tyler Seguin and Dougie Hamilton being selected. Seguin is now a superstar in Dallas, Hamilton has moved to Calgary and Boston has a Stanley Cup. Toronto’s still waiting for their first Stanley Cup, and it’s only been 48 years now since their last one.

This might be considered a deal that should have been a winner for Toronto. However, they struggled terribly over two years while Boston was acquiring the Leafs’ picks. It resulted in Tyler Seguin and Dougie Hamilton being selected. Seguin is now a superstar in Dallas, Hamilton has moved to Calgary and Boston has a Stanley Cup. Toronto’s still waiting for their first Stanley Cup, and it’s only been 48 years now since their last one.

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7. Carlo Colaiacovo and Alex Steen to St. Louis Blues for Lee Stempniak on (Nov. 23, 2008)

Alex Steen, St. Louis Blues — Alex Steen continues to flourish playing valuable top minutes as a forward for the Blues after the trade. Lee Stempniak lasted only two seasons in Toronto. He had 61 points in 123 games donning the blue and white. Steen was clearly stolen from Toronto and the gem gained by St. Louis.

Alex Steen continues to flourish playing valuable top minutes as a forward for the Blues after the trade. Lee Stempniak lasted only two seasons in Toronto. He had 61 points in 123 games donning the blue and white. Steen was clearly stolen from Toronto and the gem gained by St. Louis.

6. Tuukka Rask to Boston Bruins for Andrew Raycroft (June 24, 2006)

Tuukka Rask, Boston Bruins — This was a huge disaster for the team in blue and white. Rask was thought of as one of the highest touted prospects the Leafs have ever had, and the Leafs were looking for a replacement for their goaltender Ed Belfour. Raycroft spent two seasons in Toronto, while Rask remains in Boston as a Stanley Cup winner and a Vezina trophy winner.

This was a huge disaster for the team in blue and white. Rask was thought of as one of the highest touted prospects the Leafs have ever had, and the Leafs were looking for a replacement for their goaltender Ed Belfour. Raycroft spent two seasons in Toronto, while Rask remains in Boston as a Stanley Cup winner and a Vezina trophy winner.

5. Russ Courtnall to Montreal Canadiens for John Kordic and Sixth-Round Draft Pick (Mike Doers) (Nov. 7, 1988)

Russ Courtnall, Montreal Canadiens — This trade will always haunt former Leafs GM Gord Stellick. In 104 games with the Maple Leafs, John Kordic had 16 points total. Courtnall’s career took off after leaving Toronto as he accumulated 195 points with the Montreal Canadiens in 250 games.

This trade will always haunt former Leafs GM Gord Stellick. In 104 games with the Maple Leafs, John Kordic had 16 points total. Courtnall’s career took off after leaving Toronto as he accumulated 195 points with the Montreal Canadiens in 250 games.

4. Lanny McDonald and Joel Quenneville to the Colorado Rockies for Pat Hickey and Wilfe Paiement (Dec. 29, 1979)

Lanny McDonald, Toronto Maple Leafs — This was a huge disaster for the blue and white. Lanny McDonald and Darryl Sittler were two of the best forwards on the Leafs team in the 1970s. Management did this trade with the intent of hurting their superstar Darryl Sittler after some disagreements. This deal started the Leafs' 1980s spiral, going 301-481-98 during the decade.

This was a huge disaster for the blue and white. Lanny McDonald and Darryl Sittler were two of the best forwards on the Leafs team in the 1970s. Management did this trade with the intent of hurting their superstar Darryl Sittler after some disagreements. This deal started the Leafs' 1980s spiral, going 301-481-98 during the decade.

2. Darryl Sittler to Philadelphia Flyers for Rich Costello, Peter Ihnacak and Ken Strong (Jan. 20, 1982)

Darryl Sittler, Toronto Maple Leafs — Darryl Sittler and Leafs ownership were at odds and ownership couldn’t wait to send him out of Toronto, despite putting up fantastic statistics for the Maple Leafs. Despite not winning a Stanley Cup with Sittler, he was their best player. He went to score 178 points with the Flyers and still holds the current record of scoring 10 points in one game for the Leafs.

Darryl Sittler and Leafs ownership were at odds and ownership couldn’t wait to send him out of Toronto, despite putting up fantastic statistics for the Maple Leafs. Despite not winning a Stanley Cup with Sittler, he was their best player. He went to score 178 points with the Flyers and still holds the current record of scoring 10 points in one game for the Leafs.

1. First-Round Pick to New Jersey Devils for Defenseman Tom Kurvers (Oct. 16, 1989)

Scott Niedermayer, New Jersey Devils — Tom Kurvers had 55 points in 89 games with the Toronto Maple Leafs. The New Jersey Devils selected Scott Niedermayer with their pick acquired from Toronto. Niedermayer went on to win the Norris Trophy, Conn Smythe Trophy and four Stanley Cups in his career. Toronto’s still looking for their first Stanley Cup in almost half a century.

Tom Kurvers had 55 points in 89 games with the Toronto Maple Leafs. The New Jersey Devils selected Scott Niedermayer with their pick acquired from Toronto. Niedermayer went on to win the Norris Trophy, Conn Smythe Trophy and four Stanley Cups in his career. Toronto’s still looking for their first Stanley Cup in almost half a century.

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