Bernie Parent
While it is hard to top the level of dreadful that was the Raycroft trade. Allowing goalie Bernie Parent to leave the organization, might be a close second.
In 1971, The Leafs traded with the Philadelphia Flyers for the 25-year-old goaltender. At the time, Jacques Plante was still with the Maple Leafs and helped tutor Parent. It may have helped him develop into the player that was eventually inducted into the Hall of Fame.
Unfortunately, Parent joining the Leafs coincided with Harold Ballard taking control of the organization. It also came at the same time that a competitive league, the World Hockey Association (WHA), was created.
Ahead of the 1972-73 season, the WHA poached multiple Leafs. The league’s first signing happened to be Parent. More Leafs followed that season including Rick Ley, Jim Harrison, Brad Selwood, and Guy Trottier. Ballard, who was notoriously cheap, was unwilling to match those players’ offers.
Parent played one season in the WHA for the Philadelphia Blazers. He then wanted to return to the NHL, but not the Leafs who’s roster was decimated by the upstart league. He requested a trade and general manager, Jim Gregory obliged. The rights to Parent were returned to the Flyers for Doug Favell and a first-round pick in the 1973 NHL entry draft.
Calling this a lopsided trade is an understatement. Favell played poorly for the Leafs while Parent shone brightly. After leaving Toronto, he won two Stanley Cups, was named to two All-Star teams, finished second and fourth in Hart Trophy voting, won the Conn Smythe twice, and the Vezina twice.
While the Leafs have made many errors with their goaltenders throughout the franchise’s history, not every one of them was bad. They have had many quality players between the pipes in blue and white through the years. Hopefully, there are more positives coming in the team’s near future.