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Maple Leafs’ Five Most Regrettable Trades in History

Over the history of the Toronto Maple Leafs, the team has made many trades. What are the five worst trades the Maple Leafs have ever made?

by
Old Prof
December 21, 2024

The Toronto Maple Leafs have a long and storied history, but not every team move has worked out in their favor. Some trades, in hindsight, are particularly painful for fans to recall. These deals often came with the promise of immediate gain but resulted in long-term loss. From beloved players being sent away to potential stars slipping through their fingers, here are five trades that still haunt Maple Leafs‘ fans.

Fifth Worst Maple Leafs Trade Ever: John Kordic for Russ Courtnall (1989)

In 1989, the Maple Leafs sought to add toughness to their roster and acquired enforcer John Kordic from the Montreal Canadiens. However, the cost was steep: they sent Russ Courtnall, a speedy and productive forward, to Montreal.

Courtnall went on to enjoy a decade of success in the NHL, scoring over 200 goals after leaving Toronto. Meanwhile, Kordic’s time with the Leafs was tumultuous and short-lived. This trade remains a glaring example of prioritizing grit over skill, a philosophy that rarely leads to long-term success.

Fourth Worst Maple Leafs Trade Ever: Darryl Sittler to Philadelphia Flyers (1982)

On January 20, 1982, Toronto traded its beloved captain, Darryl Sittler, to the Philadelphia Flyers, marking the end of a bitter rift between Sittler and Leafs owner Harold Ballard. In return, the Maple Leafs received Rich Costello and a second-round pick.

At his departure, Sittler was the franchise leader in goals and points. More importantly, he was a fan favorite and a symbol of the team’s identity. This trade alienated the fanbase, and many still view it as one of the organization’s biggest missteps. It was part of a mean-spirited GM Punch Imlach saga co-conspired with the ignominious Harold Ballard.

Third Worst Maple Leafs Trade Ever: Bringing Wendel Clark Back (1995)

After trading Wendel Clark to the Quebec Nordiques, the Maple Leafs reacquired their former captain in a blockbuster deal with the New York Islanders less than two seasons later. In exchange, the Maple Leafs gave up several assets, including a 1997 first-round pick.

The Islanders used that pick to select Roberto Luongo, who had a Hall of Fame career as one of the greatest goaltenders in NHL history. While Clark’s return was celebrated, this deal underscored the risk of sacrificing future potential for sentimentality.

Second Worst Maple Leafs Trade Ever: Bernie Parent to Philadelphia Flyers (1973)

During his two seasons with the Maple Leafs, Bernie Parent showed flashes of brilliance but was never firmly established as the team’s starting goaltender. In 1973, Toronto traded him to the Flyers for a first-round pick.

Parent became a cornerstone of Philadelphia’s success, leading the Flyers to back-to-back Stanley Cups and winning both the Conn Smythe and Vezina Trophies. Meanwhile, Toronto was left without a dominant goaltender and watched Parent become a legend elsewhere. Who would have guessed?

Worst Maple Leafs Trade Ever: Trading Away the Scott Niedermayer Pick (1991)

In 1991, the Maple Leafs traded their first-round pick to the New Jersey Devils for Tom Kurvers, a move to bolster the team’s immediate prospects. However, that pick turned into the third overall selection, which the Devils used to draft Scott Niedermayer.

Niedermayer developed into one of the NHL’s all-time great defensemen, winning multiple Stanley Cups, a Conn Smythe Trophy, and a Norris Trophy. The trade became a cautionary tale for Toronto about the dangers of sacrificing high-draft picks for short-term solutions. [Ironically, the second-worst and the worst Maple Leafs trades were mirror images of each other.]

The Bottom Line: Lessons from the Past

These trades serve as stark reminders of how trades can go wrong. From losing out on Hall of Fame talents like Roberto Luongo and Scott Niedermayer to alienating fans by trading beloved players like Darryl Sittler and Wendel Clark, the Maple Leafs’ history is filled with “what if” moments.

As the Maple Leafs look to build a competitive team for the future, these cautionary tales could guide their decisions. Will they avoid similar mistakes and prioritize sustainable success, or will history repeat itself? Likely some of both.