October 16, 1989—Scott Niedermayer for Tom Kurvers
Having given up 30 goals in their first five games of the season, Leafs GM Floyd Smith decided the team needed an offensive defenceman. And he got him from New Jersey in the 27-year-old Kurvers, who was so pleased to be a Leaf that he initially refused to report and quickly played his way out of coach Brophy's favour. The cost to the Leafs: their first-round pick in the 1991 entry draft, which the Devils used to draft Norris Trophy winner, future hall-of-famer and three-time Stanley Cup Champion Scott Niedermayer. Kurvers was soon dispatched to Vancouver for Brian Bradley, who was later scooped up for free in the expansion draft by Tampa Bay, where he promptly scored 42 goals.

March 13, 1996—Kenny Jonsson and Roberto Luongo for Wendel Clark and Mathieu Schneider
A week after firing coach Pat Burns, with the team showing no signs of its 1993 and 1994 playoff success, GM Cliff Fletcher threw the fans a bone and brought Wendel Clark back from Long Island, along with defenceman Mathieu Schneider. The main pieces heading south: highly-touted young defenceman Kenny Jonsson and a first-round draft pick that Mike Milbury used to take Roberto Luongo, now widely considered the league's best goalie. Jonsson flirted with stardom, but suffered numerous concussions and returned to his native Sweden after nine seasons with the Islanders. Schneider was later traded to the New York Rangers for Alexander Karpovtsev, while Clark went to Tampa Bay after the 1997-1998 season as a free agent.

October 23, 1999—Steve Sullivan for nothing
Having sent a second-round draft pick to Boston in order to sign forward Dmitri Khristich—who soon proved as unwelcome in the Leafs' dressing room as he had been in the Capitals', Kings' and Bruins'—the Leafs were forced to put a player on waivers. Deeming the likes of Tie Domi and Kris King too valuable to the team, GM Pat Quinn instead chose a diminutive, feisty Timmins, Ont.-native who was fresh off his first of what is now six 20-goal seasons in the NHL—Steve Sullivan, one of the principals in the 1997 trade that sent Doug Gilmour to New Jersey. Sullivan has missed the entire 2007-08 campaign with a back injury, but has scored an impressive 180 goals and 281 assists in 520 games for Chicago and Nashville since leaving the Leafs.