THE STORY
In June 2006, the Toronto Maple Leafs traded goaltending prospect Tuukka Rask to the Boston Bruins in exchange for Andrew Raycroft. Rask, selected 21st overall in the 2005 NHL Draft, had yet to play an NHL game. Raycroft, the 2004 Calder Trophy winner, struggled with the Maple Leafs, while Rask developed into a Vezina Trophy-winning goaltender with the Bruins.
TEAMS / PEOPLE:
NHL teams and players
WHY IT MATTERS
This trade is widely regarded as one of the most regrettable in Maple Leafs history, as Rask's success with the Bruins highlighted the missed opportunity for Toronto.