Worst Toronto Maple Leafs Trades

The Hockey Writers highlights four of the worst trades in Toronto Maple Leafs history, identifying the 2006 deal sending Tuukka Rask to the Boston Bruins for Andrew Raycroft as the worst in the 21st century. General manager John Ferguson Jr. traded Rask believing Justin Pogge had greater potential, but Rask went on to win a Stanley Cup and a Vezina Trophy while Raycroft struggled.

The article also reviews earlier franchise missteps, including trading Darryl Sittler to the Philadelphia Flyers in 1982 for minimal return and sending Bernie Parent to Philadelphia in 1973 before Parent won two Stanley Cups. Additionally, Toronto traded a 1991 first-round pick for Tom Kurvers, allowing the New Jersey Devils to draft future Hall of Fame defenseman Scott Niedermayer.