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.

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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.

Darryl Sittler Toronto Maple Leafs
Darryl Sittler, Toronto Maple Leafs, circa 1970s (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images)

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.

25 thoughts on “Worst Toronto Maple Leafs Trades”

  1. Absolutely the worst trade of all for the disgusting Laughs was trading FRANK MAHOVOLICH so wake up people! The Leafs need a tough rough coach for such a lazy well paid loafers who have no pride in the blue and white. They also need to alter their diet to an Asian one with only fish and lots of veggies, grains and fruits…Sotty Bowmen wanted the LAUGHS but their horrifying management then led by a Socialistic teacher’s Union said no! Also, the Airhead Canada Centre need fewer white collars and more blue collar men in the seats to, yes, throw Wendel Clark, Darcy Tucker, TI DOMI, GARY ROBERTS, GILMOUR, and Don Cherry sweaters on the ice…actually, I would not attend their games and leave my season seat empty. Kessel never checks yet gets away with this?! How many other leading scorers do this?! Appalling leader as is Faneuf!

  2. The worst trade of all time was Russ Courtnall to Montreal for John Kordic.Cortnall went on to get over 100 points and Kordik picked up 2 points and never really did anything for Toronto as his best fighting was behind him.

  3. Imlach trading Frank Mahovlich, Peter Stemkowski and Gary Unger for Norm Ullman, Paul Henderson and Floyd Smith. One of the best players ever plus two solid, long lived centres for three guys who either couldn’t play very well or didn’t want to play for Toronto. And Floyd Smith continued to ruin the Leafs for years as maybe the worst GM in league history.

    Leafs haven’t had a decent centre other than Sittler since then and Imlach returned from the dead and traded him away too.

    • I agree that any article dealing with bad Leaf trades should include this six player trade including Mahovlich and Ullman. However, anybody suggesting the Leafs haven’t had a worthy centreman since Sittler should look at videos of Gilmour’s ’93 campaign and Sundin’s entire career wearing the blue and white.

  4. the bruins got the better of the trade with rask. but he has come along way. he got sent down to providence the first time when tim thomas was in net then came back 110% better and started a career and will most likely end it in boston. you don’t see this often but I give props to the goaltender coach in providence for helping him. as well as in boston. which got him a 8 year 110 mil contract. imagine that? over Andrew Raycroft who doesn’t even play anymore. the leafs got jipped on that van riems dyke and kulemin are currently the stars for the leafs along with lupul and leopold. if he is still there. I know my hockey been watching and playing it since I was 4. now I got health issues and I’m 33. basketball and football are my other sports the shooting in Ottawa was horrible and tragic the boston national anthem singer rene recourt sang both the Canadian and American national anthem before the game last night where the bruins lost to the islanders 3-1.

  5. What about the Phil Kessel trade? We lost out on getting Tyler Seguin and Dougie Hamilton. Plus the Bruins won the cup as well, while Leaf Nation is still waiting! Why this trade was not even mentioned is surprising! Anyone else agree!

    • That statement hurts my brain. Trading what turned out to be a tier 1.5 player with attitude issues (that you couldn’t have known you were getting anyway) and an okay player for a tier 1 goal scorer who is the only player since Sundin to live up to his hype in Toronto. Even if this trade wasn’t favorable for the leafs (which it is) it would at least be close.

  6. Trading their first round draft pick in 1997 to the New York Islanders for D.J, Smith, Mathieu Schneider, and Wendel Clark. Although I’m a huge fan of Clark, and strongly agree with him being included, the Islanders used that pick to draft Roberto Luongo

    • Don’t forget Kenny Jonsson was sent the other way as well. The Leafs did parlay Schneider into Mike Van Ryn though! (via Karpovtsev and McCabe).

  7. almost every trade the ny rangers made up to and until rick nash. whether it was players or draft choices the rangers always got the short end of the stick.

  8. Devin – just chatted with a former Leaf who was with the team when Sittler was traded. There is so much to that trade regarding the player agent and the GM – but no doubt it was a bad trade! Interesting piece.

  9. For all-time, Randy Carlyle to Pittsburgh for squat could be considered as well. Agree with the top 3 ever though.

  10. How about the Owen Nolan for McCauley, Boyes, and Stuart trade?? Has to be somewhere near the top. Or even the Toskala trade if were only talking 21st century. Lots of bad trades with the Sharks

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