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
SUNRISE, FL – FEBRUARY 18: Head coach Randy Carlyle of the Toronto Maple Leafs   (Photo by Joel Auerbach/Getty Images)

#5. Randy Carlyle Gets Traded and Becomes NHL’s Best Defenseman

The Trade:

  • Toronto Maple Leafs acquire: Dave Burrows
  • Pittsburgh Penguins acquire: Randy Carlyle and George Ferguson

Randy Carlyle may be most-known for coaching the Toronto Maple Leafs (“Good one, Randy”) instead of playing for them, but the 64-year-old was drafted by the team in 1976 and played two seasons in Toronto.

I’m not sure what the team was thinking when they made this move. It was during the Harold Ballard Era, so I mean anything was possible back then and nobody was safe. However, the Sudbury, ON native had ripped up junior hockey in his hometown before joining the Toronto Maple Leafs and looked like a great prospect.

However, after not producing much at the NHL-level, two years later Carlyle was sent to the Pittsburgh Penguins with George Furgson for an aging veteran defenseman named Dave Burrows.

Burrows was at the end of his career, while Carlyle was just getting started, and boy did he ever take off. Two years after getting traded from the Toronto Maple Leafs, Carlyle turned into one of the best defenseman in the NHL. His 1980-81 season will always be remembered in Pittsburgh, as he scored 16 goals, registered 83 points and won the Norris Trophy.

And it’s not like Carlyle was a flash in the pan or anything that one season. For the next decade after the Toronto Maple Leafs moved on from him, he continued to produce year-after-year. Even when he got traded to the Winnipeg Jets, he continued to have a great career, playing over 1000 NHL games.