Worst trades - Toronto Maple Leafs
| Toronto Maple Leafs acquire | Date | Boston Bruins acquire | ||
|---|---|---|---|---|
 | Andrew Raycroft | June 24, 2006 | rights to Tuukka Rask |  |
| New Jersey Devils acquire | Date | Toronto Maple Leafs acquire | ||
|---|---|---|---|---|
 | 1991 1st round pick (#3-Scott Niedermayer) | October 16, 1989 | Tom Kurvers | |