Top 10 Worst Trades in Toronto Maple Leafs History

Toronto Maple Leafs goaltender Andrew Raycroft makes a blocker save as Boston's Wayne Primeau looks behind him for a rebound during game between the Toronto Maple Leafs and Boston Bruins at the Air Canada Centre in Toronto, Canada on November 28, 2006. (Photo by Jay Gula/Getty Images)
Toronto Maple Leafs goaltender Andrew Raycroft makes a blocker save as Boston's Wayne Primeau looks behind him for a rebound during game between the Toronto Maple Leafs and Boston Bruins at the Air Canada Centre in Toronto, Canada on November 28, 2006. (Photo by Jay Gula/Getty Images)
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Toronto Maple Leafs
Canadian professional ice hockey player Bernie Parent #1 (left), goalie of the Philadelphia Flyers, defends the goal during an away game against the New Yorjk Rangers . (Photo by Melchior DiGiacomo/Getty Images)

#4. Leafs Give Up on Future Vezina Trophy and Conn Smythe Winner

The Trade:

  • Toronto Maple Leafs acquire: 1973 First Round Pick (Bob Neely) and Doug Favell
  • Philadelphia Flyers acquire: Bernie Parent

The history of Toronto Maple Leafs goaltenders in deep. From Johnny Bower to Curtis Joseph, the list goes with regards to great net-minders. However, that list could have been a little longer if they decided not to move on from a future Conn Smythe trophy winner named Bernie Parent.

Splitting time with Jacques Plante, the Toronto Maple Leafs decided to keep Plante (who was 43-years-old) instead of the 26-year-old Parent and shipped him to Philadelphia after only two seasons. And it may be one of the worst decisions they ever made.

In back-to-back years after leaving the Toronto Maple Leafs, Parent joined the “Broad Street Bullies” and not only won back-to-back Stanley Cup championships, but he was the Conn Smythe winner in both. To put a cherry on top of everything, he was also named the NHL’s best goaltender, taking home the Vezina Trophy in both championship seasons.

So essentially, the Toronto Maple Leafs moved on from the best goaltender in the world for a decent defenseman and mediocre net-minder. Who knows if Parent would have been able to win a Vezina Trophy in Toronto, but that’s tough to see.