Worst trades
| Winnipeg Jets acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Brayden Yager | August 22, 2024 | Rutger McGroarty |  |
| Washington Capitals acquire | Date | Nashville Predators acquire | ||
|---|---|---|---|---|
 | Michael Latta | April 3, 2013 | Filip Forsberg |  |
| Martin Erat | ||||
| Montreal Canadiens acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
 | Tom Pyatt | June 30, 2009 | Pavel Valentenko |  |
| Scott Gomez | Ryan McDonagh | |||
| Michael Busto | 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 | September 30, 2006 | Mike Ribeiro |  |
| 2007 5th round pick (#142-Andrew Conboy) | 2008 6th round pick (#176-Matthew Tassone) | |||
| Los Angeles Kings acquire | Date | Carolina Hurricanes acquire | ||
|---|---|---|---|---|
 | Oleg Tverdovsky | September 29, 2006 | Tim Gleason |  |
| Jack Johnson | 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 | December 5, 2005 | Matt Ellison |  |
| Patrick Sharp | 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 | March 10, 2003 | Chris Gratton |  |
| 2004 3rd round pick (#71-Andrej Sekera) | 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 | July 11, 2001 | Kris Beech | |
| Frantisek Kucera | Ross Lupaschuk | |||
| Michal Sivek | ||||
| future considerations | ||||
| New York Islanders acquire | Date | Ottawa Senators acquire | ||
|---|---|---|---|---|
 | Alexei Yashin | June 23, 2001 | Bill Muckalt |  |
| Zdeno Chara | ||||
| 2001 1st round pick (#2-Jason Spezza) | ||||
| Florida Panthers acquire | Date | New York Islanders acquire | ||
|---|---|---|---|---|
| Olli Jokinen | June 24, 2000 | Oleg Kvasha | |
| Roberto Luongo | 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 | February 6, 1998 | Trevor Linden | |
| Bryan McCabe | ||||
| 1998 3rd round pick (#68-Jarkko Ruutu) | ||||
| Los Angeles Kings acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
| Glen Murray | March 18, 1997 | Ed Olczyk | |