Worst trades in NHL history

Montreal Canadiens acquire Date New York Rangers acquire
Tom Pyatt
Scott Gomez
Michael Busto
June 30, 2009
Pavel Valentenko
Ryan McDonagh
Doug Janik
Christopher Higgins
Boston Bruins acquire Date Chicago Blackhawks acquire
Brandon Bochenski
February 3, 2007
Kris Versteeg
2008 conditional 5th round pick (if Bochenski plays more than 80 NHL games between the day of the trade and the end of the 2007-08 season) (not exercised)
Montreal Canadiens acquire Date Dallas Stars acquire
Janne Niinimaa
2007 5th round pick (#142-Andrew Conboy)
September 30, 2006
Mike Ribeiro
2008 6th round pick (#176-Matthew Tassone)
Los Angeles Kings acquire Date Carolina Hurricanes acquire
Oleg Tverdovsky
Jack Johnson
September 29, 2006
Tim Gleason
Eric Belanger
Toronto Maple Leafs acquire Date Boston Bruins acquire
Andrew Raycroft
June 24, 2006
rights to Tuukka Rask
Chicago Blackhawks acquire Date Philadelphia Flyers acquire
Eric Meloche
Patrick Sharp
December 5, 2005
Matt Ellison
2006 3rd round pick (#66-Ryan White)
Edmonton Oilers acquire Date St. Louis Blues acquire
Chris Pronger
August 2, 2005
Eric Brewer
Doug Lynch
Jeff Woywitka
Washington Capitals acquire Date New York Rangers acquire
Anson Carter
January 23, 2004
Jaromir Jagr
Buffalo Sabres acquire Date Arizona Coyotes acquire
Daniel Briere
2004 3rd round pick (#71-Andrej Sekera)
March 10, 2003
Chris Gratton
2004 4th round pick (#112-Liam Reddox)
Calgary Flames acquire Date Atlanta Thrashers acquire
Ruslan Zainullin
November 15, 2002
Marc Savard
Tampa Bay Lightning acquire Date Florida Panthers acquire
Dan Boyle
January 7, 2002
2003 5th round pick (#162-Martin Tuma)
Washington Capitals acquire Date Pittsburgh Penguins acquire
Jaromir Jagr
Frantisek Kucera
July 11, 2001
Kris Beech
Ross Lupaschuk
Michal Sivek
future considerations
New York Islanders acquire Date Ottawa Senators acquire
Alexei Yashin
June 23, 2001
Zdeno Chara
Bill Muckalt
2001 1st round pick (#2-Jason Spezza)
Florida Panthers acquire Date New York Islanders acquire
Olli Jokinen
Roberto Luongo
June 24, 2000
Oleg Kvasha
Mark Parrish
Anaheim Ducks acquire Date Calgary Flames acquire
Jean-Sebastien Giguere
June 10, 2000
2000 2nd round pick (#43-Matt Pettinger)
Los Angeles Kings acquire Date Nashville Predators acquire
future considerations
June 26, 1998
Kimmo Timonen
Jan Vopat
Vancouver Canucks acquire Date New York Islanders acquire
Todd Bertuzzi
Bryan McCabe
1998 3rd round pick (#68-Jarkko Ruutu)
February 6, 1998
Trevor Linden
Los Angeles Kings acquire Date Pittsburgh Penguins acquire
Glen Murray
March 18, 1997
Ed Olczyk
Buffalo Sabres acquire Date Edmonton Oilers acquire
Miroslav Satan
March 18, 1997
Craig Millar
Barrie Moore
St. Louis Blues acquire Date Ottawa Senators acquire
Pavol Demitra
November 27, 1996
Christer Olsson