Worst Toronto Maple Leafs Trades

There have been some horrible, terrible and embarrassing trades by the Toronto Maple Leafs in team history. But in recent memory, the number one worst trade blows all the others out of the water — or perhaps blows the Leafs off the trees. Everything about this deal was bad. They chose the wrong player to trade. The wrong time to make the trade. And last but not least, the wrong team to trade with.

To warm you up, here are a few of the worst Leafs trades of all time.

Darryl Sittler

Leafs Trade Sittler to the Flyers for Rich Costello, Peter Ihnacak & Ken Strong

In Jan. 1982, the Leafs traded their captain and best player to the Flyers for virtually zilch. Darryl Sittler has the second most points ever in a Leafs’ uniform with 916 — only Mats Sundin is ahead of him with 987. He was inducted into the Hockey Hall of Fame in 1989 after his retirement.

Sittler was loved by all true Leafs fans for his passion for the game. What they got in return…

Costello played 12 games in his NHL career. Strong, who was a second-round pick in the trade, played 15 career NHL games. Ihnacak was the only player they got who could be deemed ‘respectable’. He scored 28 goals and 66 points in his first year in the Blue and White. After that season, he would never again score 20 goals or 50 points. All in all, this was a horrifying trade for the Leafs, one they may very well never forget.

Bernie Parent

Leafs Trade Parent & Larry Goodenough to the Flyers for Bob Neely & Doug Favell

In May 1973, the Toronto Maple Leafs made their first brutal trade with the Philadelphia Flyers. They sent Bernie Parent, who had requested a trade, to Philadelphia for a couple of below average players. Parent was traded after leaving the team to play in the World Hockey Association.

However, it was what Parent did after the trade that people will remember. In his first two years with Philadelphia, he won two Stanley Cups, two Vezina Trophies and two Conn Smythe Awards. Essentially, he was the best player in the entire league.

The Leafs received Bob Neely, who was a first-round pick but played just over four seasons in Toronto, posting average numbers as a defenceman. Doug Favell was a backup goalie for the Leafs for just two seasons before being traded to Colorado along with Neely for cash. Just six years after their last Stanley Cup, the Toronto Maple Leafs traded a guy who almost solely brought two Cups to Philadelphia himself.

Just six years after their last Stanley Cup, the Toronto Maple Leafs traded a guy who almost solely brought two Cups to Philadelphia himself.

Scott Niedermayer

Leafs Trade 1991 1st Round Pick to the Devils for Tom Kurvers

In Oct. 1989, the Leafs traded away their 1991 first-round pick, for the late Tom Kurvers. Kurvers put up 55 points in 89 games with Toronto before being traded away to Vancouver. The Leafs were then just straight-up bad in 1990-91 and finished second last in the league. Lucky for them, the San Jose Sharks were created, meaning the Devils would pick third instead of second overall with the Leafs’ pick.

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New Jersey ended up taking Scott Niedermayer, who went on to be a Hall of Fame defenceman who won a Norris Trophy in 2004 and a Conn Smythe Trophy in 2007. — not to mention four Stanley Cups. Oh, and he also won a World Junior Championship in 1991, a World Cup in 2004 and last but certainly not least, an Olympic Gold Medal in 2002 and 2010. He is now regarded as the player who won everything. Too bad for Toronto, none of it was while wearing a Toronto Maple Leafs jersey.

And now, for the worst Leafs trade in the 21st century. Drumroll, please…

Tuukka Rask

Leafs Trade Tuukka Rask to the Bruins for Andrew Raycroft

In June 2006, John Ferguson Jr. made a trade that Leafs fans will not forget for a very long time. He dealt his 2005 first-round pick for the 2003-04 Calder Trophy Winner. His incentive was that he possessed two top-end talent goaltenders of the future in Justin Pogge and Tuukka Rask. He simply thought, at the time, Pogge had the better potential of the two. Boy oh boy, did he and the Leafs management get that one wrong.

Raycroft played one full season for the Leafs putting up below average numbers. Then, in his second season in Toronto, he played just 19 games before being traded to Colorado. He was downright terrible in the Leafs’ sweater.

On the other hand, Rask developed well. He won the Stanley Cup in 2011 and the Vezina Trophy in 2013-14. He cemented himself as one of, if not the best goaltender in the NHL each year. He also shut the door on the Leafs in the 2013 Playoffs, as Boston came back from a third-period 4-1 deficit to win in overtime of Game 7.

Meanwhile, for the Toronto Maple Leafs, Justin Pogge went on to play a grand total of seven career NHL games. He moved on to play in the Swedish Hockey League for Farjestad and retired after the 2022-23 season.

* Written by former THW contributor Devin Slawson and originally published on Oct. 23, 2014.