Worst trades
| 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 |  |
| Vancouver Canucks acquire | Date | Pittsburgh Penguins acquire | ||
|---|---|---|---|---|
 | Markus Naslund | March 20, 1996 | Alek Stojanov |  |
| Anaheim Ducks acquire | Date | Winnipeg Jets acquire | ||
|---|---|---|---|---|
 | 1996 4th round pick (#92-Kim Staal) | February 7, 1996 | Chad Kilger |  |
| Teemu Selanne | Oleg Tverdovsky | |||
| Marc Chouinard | 1996 3rd round pick (#62-Per-Anton Lundstrom) | |||
| Detroit Red Wings acquire | Date | Winnipeg Jets acquire | ||
|---|---|---|---|---|
 | Kris Draper | June 30, 1993 | future considerations (1$) | |
| Buffalo Sabres acquire | Date | Chicago Blackhawks acquire | ||
|---|---|---|---|---|
| Dominik Hasek | August 7, 1992 | Stephane Beauregard |  |
| 1993 4th round pick (#90-Eric Daze) | ||||
| New Jersey Devils acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
 | 1991 1st round pick (#3-Scott Niedermayer) | October 16, 1989 | Tom Kurvers |  |
| St. Louis Blues acquire | Date | Detroit Red Wings acquire | ||
|---|---|---|---|---|
| Paul MacLean | June 15, 1989 | Bernie Federko | |
| Adam Oates | Tony McKegney | |||
| Calgary Flames acquire | Date | St. Louis Blues acquire | ||
|---|---|---|---|---|
 | Rob Ramage | March 7, 1988 | Steve Bozek | |
| Rick Wamsley | Brett Hull | |||
| Washington Capitals acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
 | Bob Crawford | January 1, 1987 | Bobby Carpenter |  |
| Kelly Miller | 1989 2nd round pick (#40-Jason Prosofsky) | |||
| Mike Ridley | ||||
| Boston Bruins acquire | Date | Vancouver Canucks acquire | ||
|---|---|---|---|---|
 | Cam Neely | June 6, 1986 | Barry Pederson | |
| 1987 1st round pick (#3-Glen Wesley) | ||||
| Los Angeles Kings acquire | Date | Washington Capitals acquire | ||
|---|---|---|---|---|
 | Brian Engblom | October 18, 1983 | Larry Murphy | |
| Ken Houston | ||||
| Boston Bruins acquire | Date | New York Rangers acquire | ||
|---|---|---|---|---|
| Rick Middleton | May 26, 1976 | Ken Hodge Sr. | |
| St. Louis Blues acquire | Date | Detroit Red Wings acquire | ||
|---|---|---|---|---|
| Wayne Connelly | February 6, 1971 | Red Berenson | |
| Garry Unger | Tim Ecclestone | |||
| Montreal Canadiens acquire | Date | California Golden Seals (Oakland) acquire | ||
|---|---|---|---|---|
 | cash | May 22, 1970 | 1970 1st round pick (#10-Chris Oddleifson) | .gif){kind=small} |
| 1971 1st round pick (#1-Guy Lafleur) | Ernie Hicke | |||
| Francois Lacombe | ||||
| Comment: This trade changed the history of hockey. Imagine if Lafleur wasn't part of the great 70s Canadiens teams, they would still have had an excellent roster, but would they have won as much? | ||||