Maple Leafs’ One That Got Away: Tuukka Rask

The Hockey Writers argues that trading draft pick Tuukka Rask to the Boston Bruins in 2006 was a major loss for the Toronto Maple Leafs. General manager John Ferguson Jr. sent Rask to Boston on June 24, 2006, in exchange for goaltender Andrew Raycroft to avoid a rebuild, but Raycroft struggled to regain his earlier Calder Trophy form.

While Toronto dealt with years of goaltending instability before acquiring Frederik Andersen, Rask flourished in Boston, winning a Stanley Cup and the 2013-14 Vezina Trophy. The article notes that while retaining Rask could have changed the franchise's trajectory, it might have also prevented Toronto from drafting Auston Matthews, Mitch Marner, and William Nylander.