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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New York Rangers forward Jason Ward #16 watches the puck trickle over the goal line for a goal behind Toronto Maple Leaf   (Photo by Jay Gula/Getty Images)

#2. The Infamous Rask for Raycroft Deal

The Trade:

  • Toronto Maple Leafs acquire: Andrew Raycroft
  • Boston Bruins acquire: Tuukka Rask

Every NHL fan knows this trade and if you’re a Toronto Maple Leafs supporter, it still haunts you to this day.

Two years prior to making this trade, Andrew Raycroft had won the Calder Trophy as the NHL’s rookie of the year. It’s a great accomplishment, but if the Boston Bruins were willing to ship him away for an unknown goaltender from Finland, isn’t that fishy? If you’re the GM of the Toronto Maple Leafs at the time, aren’t you like, “Well that was easy?”

The Boston Bruins had Tim Thomas ready to become the starter, so they gave Andrew Raycroft the opportunity for more playing time in Toronto, but shipping away a 25-year-old goalie isn’t a decision that most teams do. It’s almost like they knew what they were doing, while the Toronto Maple Leafs had no friggin’ clue!

Oh wait, that’s exactly what happened.

I’ll paint the picture lightly, but things did not go well in Toronto for Raycroft. In fact, he only played two seasons, averaging a save percentage much lower than .900%. While Raycroft was stinking it up in Toronto, the Boston Bruins were patiently waiting for Tuukka Rask to develop into their future number-one goaltender.

Before they knew it, the Finnish superstar would win the Vezina Trophy and become one of the best goaltenders in the NHL. The Toronto Maple Leafs had two star goaltending prospects at the time and chose the wrong one to keep. Justin Pogge was the other goalie and he did even worse than Raycroft, as he only played seven career NHL games.

This is a trade that still hurts, as Rask could have been the goalie for the past decade for the Toronto Maple Leafs, but instead, he beats the Leafs every spring.