Toronto Maple Leafs: Top Five Worst Trades

G LContributor IJanuary 8, 2009

With many Leaf fans puzzled at an allegedly rebuilding team trading away a draft pick for a 37-year-old veteran in Brad May, Brian Burke can always take comfort that he wasn’t involved in any of these stinkers. Here is my list of the five worst Leaf trades of all-time:


No. 5: Toronto trades Russ Courtnall to the Montreal Canadiens for Jon Kordic and a Sixth Round Pick in 1989.

The Leafs were looking to add some toughness and grit, and the Habs took full advantage of it. Gord Stellick will never live this trade down, as Kordic recorded 446 penalty minutes and 16 points in 104 games as a Leaf, while Courtnall gradually improved over parts of four seasons with the Habs and ended up with 82 goals and 195 points in 250 games.

This is likely one the worst trades ever based on the point difference between the two players. The Leafs eventually dumped Jon Kordic and Paul Fenton for a fifth round pick.


No. 4: Toronto trades Darryl Sittler to the Philadelphia Flyers for Rich Costello, a Second Round Pick in 1982 (Peter Ihnacak) and Future Considerations (Ken Strong).

This was a dark day for the Toronto Maple Leafs. They 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.

He recorded 178 points in 191 games as a Flyer, and then added one last season in Detroit before retiring and going on to the Hall of Fame. It’s just sad what they settled for in return. Ken Strong? 15 NHL games, then disappeared to Austria. Rich Costello? 12 NHL games.

Only Peter Ihnacak made the club, and after recording a 66-point season he was able to register just 201 points in his final 337 games as a Leaf before returning to Europe.

Although there is no guarantee that the Leafs would have picked Roberto Luongo, the Leafs definitely took the grunt of this trade. Cliff Fletcher was pressured into bringing back fan favorite Clark, but after only one 30 goal season followed by a 12 goal season, Wendel was eventually lost to free agency.

While Haggerty was a bust and Hendrickson was back in Toronto the next season, Kenny Jonsson was a fixture in New York and played 597 games for New York, recording 232 points.

Mathieu Schneider was solid for the Leafs but was then traded for Alex Karpovtsev, who in turn brought in Bryan McCabe. The Leafs are really wishing they had Luongo between the pipes now.

This is easily one of the most lopsided trades of all time, as in Bernie Parent’s first two seasons after being traded he won two Stanley Cups, two Conn Smythe trophies, and two Vezina trophies. He was also incredible during the regular season, posting a record of 177-60-57 in 298 games over six seasons.

Doug Favell lasted just three mediocre seasons with the Leafs and Neely posted decent numbers but was gone after four seasons on defense.

The New Jersey Devils got a player who had 476 points in 892 games and helped them to Stanley Cups in 1995, 2000, and 2003 (and nearly another one in 2001).

He then went on to sign with the Anaheim Ducks as a free agent, where he added another 157 points in 209 games, and added a fourth Stanley Cup ring to his resume in 2007. He has won a Memorial Cup and gold medals at the World Junior Championship, the World Championship, the World Cup of Hockey, and Winter Olympics.

I am of course talking about Scott Neidermayer, a franchise player who without a doubt would have made a huge impact on the Maple Leafs organization.

While the Leafs in turn got a player who had a respectable 52 points in his first season with the Leafs, but followed that up the next season with only three assists through 19 games before being traded to Vancouver for Brian Bradley, a player eventually lost in the 92’ expansion draft for nothing.

Not much of a Neidermayer fan? The Leafs could have had Peter Forsberg, Brian Rolston, Alexei Kovalev, Markus Naslund, Glen Murray, or Martin Rucinsky instead.

Toronto trades Fredrick Modin to the Tampa Bay Lightning for Cory Cross and a Seventh Round Pick.


Toronto trades Tukka Rask to the Boston Bruins for Andrew Raycroft.

Toronto trades Larry Murphy to the Detroit Red Wings for Future Considerations.

Toronto trades Alyn McCauley, Brad Boyes and a 2003 First Round Pick (Mark Stuart) to the San Jose Sharks for Owen Nolan.

Toronto trades Jason Smith to the Edmonton Oilers for a Second Round Pick in 2000 (Kris Vernarsky).

Toronto trades Adam Mair and a 2nd round draft pick (Mike Cammalleri) for Aki Berg.