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Top 10 Worst Trades in Toronto Maple Leafs History

By Stephen Nixon

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
Toronto Maple Leafs – Darryl Sittler on December 9, 1981 at Maple Leaf Gardens in Toronto (Photo by Graig Abel/Getty Images) /

#10. Leafs Send Their Best Player to Philadelphia

The Trade:

  • Toronto Maple Leafs acquire: Rich Costello, future considerations and 1982 2nd Round Pick (Peter Ihnacak)
  • Philadelphia Flyers acquire: Darryl Sittler

You shouldn’t trade the greatest point-producer in Toronto Maple Leafs history, but you don’t tell Harold Ballard what to do.

The relationship between Sittler and Ballard wasn’t pretty. Sittler felt more betrayed by Ballard with every passing moment. The controversial owner fired popular head coach Roger Neilson and then decided to trade one of Sittler’s best-friends, Lanny McDonald.

The relationship continue to worsen daily, until Sittler agreed to leave. As a local kid, living his dream playing for the Toronto Maple Leafs, while excelling at it, it’s not like he wanted to move on, but it was necessary. Ballard made a lot of terrible moves, but ruining the relationship with Sittler was one of his worst decisions.

The Toronto Maple Leafs received Peter Ihnacak in the package for Sittler and although he had a good few seasons, nobody could replace the captain. Sittler only played for another four seasons after he was traded from Toronto, but would still rack up great point-totals, scoring 43 goals and registering 83 points in his second season in Philadelphia.

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