10. Tuukka Rask to Boston for Andrew Raycroft (2006)
The moment heard about this trade I hated. At the World Juniors earlier that year Rask had been named the top goalie at the tournament. Raycroft was coming off a season where his save percentage was a dismal .879 and just eight wins in 30 starts. What was there to like? And there have been quite a few goalies who after great rookie season have had their careers crash and burn. The classic example was Jim Carey. And of course my worst fears came true. This past season Rask has become one of the top goalies in the league and pushed the previous season's Vezina Trophy winner to the bench as a back up. As for Raycroft, he is will finish his career as a backup too.
9. Fredrick Modin to Tampa Bay for Corey Cross (2001)
Modin developed into a solid winger for Tampa Bay and is still playing in the NHL. The Leafs lacked that big winger to play with Sundin until they signed Gary Roberts as a free agent. Cross was one of the largest soft players ever to play in the NHL. He was a frequent healthy scratch with the Leafs and booed by the fans.
8. Larry Murphy to Detroit for future considerations (1997)
Larry Murphy had a stellar career stretching 21 seasons. He was on 4 Stanley Cup teams and inducted into the Hockey Hall of Fame in 2004. In 1995 after being named to the second-team All-Stars Murphy was traded to his hometown Leafs from the Penguins for Dmitri Mironov and a second round pick. Leafs fans booed Murphy, the highest paid player on the Leafs, mercilessly as a scapegoat for the lack of success the team was having. So they literally gave him away and paid one-third of his salary too. Fortunately for Murphy he was able to win 2 more Cups with Detroit.
7. Kenny Jonsson, Sean Haggerty, Darby Hendrickson and a 1st Round Pick in 1997 (Roberto Luongo) to the New York Islanders for Wendel Clark, Mathieu Schneider and D.J. Smith (1996)
I should tell you that I ignored the fact that the draft pick sent to the Islanders turned out to be Luongo. There is no guarantee that the Leafs would have picked him. Had the Leafs actually traded to Luongo to New York, then this trade would be much higher on the list. After trading Wendel Clark when his market value was at its peak (how often have the Leafs done that) they bring back the broken down winger two years later. The trade was only to appease the fans who fell in love with the hard working Clark. Leaf fans have always favoured rugged players over skilled players which is why Clark was so much more popular than Sundin. Meanwhile, while Haggerty was a bust and Hendrickson was back in Toronto the next season, Kenny Jonsson was a fixture in New York for a decade. He played 597 games for New York, recording 232 points, many of them in a time where quality Leafs blueliners were few and far between. Mathieu Schneider is the only reason this trade wasn't higher on this list. But he couldn't make up for the mediocre play of Clark.
6. Lanny McDonald and Joel Quenville to the Colorado Rockies for Pat Hickey and Wilf Paiement (1979)
This was a trade that began the franchise’s descent into the hell that was the 80s, a decade in which the Leafs had a record of 301-481-98 between 79-80 and 89-90 (a win percentage of .398, during a time in which surrendered 660 more goals than they scored). It is also widely reported that the deal by Punch Imlach was intended to hurt Leafs captain Darryl Sittler and make him waive his no trade contract. Only in Toronto would a personal vendetta come before the success of the club. At first glance, the stars in this trade worked out well. Toronto got 187 games and 203 points out of Paiement, while Colorado got 142 games and 141 points from McDonald. Paiement even recorded a 40 goals and 97 points in his first full season in Toronto. But when he dropped to 18 goals and 58 points the following seasons, the Leafs traded him to Quebec for Miroslav Frycer and a 7th rounder. Yes, that’s right; Miroslav Frycer was all the Leafs had to show for dealing heart-and-soul Lanny McDonald. This trade might have moved up a notch or two on this list if the Rockies had gotten more out of McDonald. But he moved on to Calgary where he scored 66 goals one season and a Stanley Cup.
5. Darryl Sittler to the Philadelphia for Rich Costello, a 2nd Round Pick in 1982 (Peter Ihnacak) and Future Considerations (Ken Strong) (1981)
I'm still angry about this deal. The Leafs traded their captain, their best player since Dave Keon, and a man just 84 points away from becoming the first Toronto player ever to record 1,000 points in a Maple Leaf uniform. They got garbage in return.
4. Russ Courtnall to the Montreal for John Kordic and a 6th Round Pick in 1989 (Mike Doers) (1989)
Thank you Mr. Stellick! The Leafs needed a goon, and the Habs were interested in Russ Courtnall. Since Leaf Head Coach John Brophy didn't think much of the smooth skating Courtnall the deal was made. Kordid got 446 penalty minutes and 16 points in 104 games as a Leaf, while Courtnall gradually improved over parts of four seasons with the Habs. He ended up with 82 goals and 195 points in 250 games for Montreal. Meanwhile, the Habs turned Russ Courtnall into Brian Bellows, who won a Stanley Cup with the Habs. And Courtnall kept on being a decent offensive player in the NHL. Kordic wasn't really a hockey player. To add insult to injury he wore #27 with the Leafs - the number worn by Frank Mahovlich and Darryl Sittler. On August 8, 1992, after overdosing on drugs and being involved in a struggle with police at his hotel, Kordic died.
3. Bernie Parent and a 2nd Round Pick in 1973 (Larry Goodenough) to the Philadelphia for a 1st Round Pick in 1973 (Bob Neely) and Future Considerations (Doug Favell) (1973)
It's not every day you get to trade away a Hall of Fame goalie. Bernie Parent was a a young Toronto goalie that left the club to play in the World Hockey Association, which instantly made him an outcast in the eyes of Leafs management and ownership. Having played previously in Philadelphia with the NHL’s Flyers and the WHA’s Blazers, he requested a trade to Philadelphia. His request was granted… and in his first two seasons with the Flyers, Bernie Parent won two Stanley Cups, two Conn Smythe trophies as the MVP of the playoffs, and two Vezina trophies. So he was the best goaltender in the league, and the most valuable player on the back-to-back Stanley Cup champions. Doug Favell meanwhile was a complete bust. The Leafs didn't get much value out of the draft pick. Bob Neely posted decent numbers as a defenseman, but after four seasons and change he was gone.
2. Randy Carlyle and George Ferguson to the Pittsburgh for Dave Burrows (1978)
Jim Gregory was a very good GM for the Leafs but this trade was a stinker. He was of a mind that Burrows was the missing piece needed to carry the Leafs to the Stanley Cup. Dave Burrows did absolutely nothing for Toronto. In just over 2 seasons, he recorded 32 points in 151 games, and then he was gone. But Randy Carlyle was the true gem of this deal. He played 397 games as a Penguin, recording 323 points. He won the Norris trophy recording 83 points in 1980-81. Oh so how did the Leafs do in the playoffs with Burrows in their lineup? Over two seasons they were 2-7. And no Stanley Cups.
1. 1st Round Pick in 1991 to the New Jersey Devils for Tom Kurvers (1989)
The mother of bad trades thanks to GM Floyd Smith. Once again the GM was convinced that journeyman defenseman Tom Kurvers was all the Leafs needed to compete for a Cup. Although earlier in the list I ignored a draft pick that turned out to be Roberto Luongo, this trade was a straight exchange for first round pick so it is hard to ignore. Similar to the Kessel trade, Smith did not anticipate when he made the trade that the team would collapse the following season. But they did. In fact the Leafs were pretty competitive during the 1989-90 season with a potent offense led by Gary Leeman's 51 goals. The Leafs were bad in 1990-91… so bad that they were on pace to finish last in the NHL behind the Quebec Nordiques. And Toronto was feeling the sting of Kurvers not working out as expected. So the Leafs traded prospect Scott Pearson and a pair of 2nd Round picks to Quebec for Aaron Broten, Lucien Deblois and Michel Petit. The trade was solely so they wouldn't finish last overall and giving the Devils the right to draft Eric Lindros. So New Jersey ends up picking third and has to settle for Scott Niedermayer. Niedermayer was only one of the best defenseman to play the game. He's the only player in hockey history to have won a Stanley Cup (4 to exact), Olympic gold medal (2), World Championship, World Cup, Memorial Cup and World Junior title. He won the Norris Trophy in 2004 and the Conn Smythe in 2007.