Andrew Raycroft
Warning: This is going to be painful.
If you aren’t familiar with the Leafs acquisition of Andrew Raycroft, congratulations, you have probably been sleeping well. On June 24, 2006, the Maple Leafs General Manager, John Ferguson Jr. pulled the trigger on what may be the worst trade in team history.
The Leafs had two very promising young goalies in their system, Justin Pogge and Tuukka Rask. There was no need to keep both of them so a decision was made to send one to the Boston Bruins in exchange for the former Calder Memorial Trophy winner, Raycroft.
This misstep is only made worse with the knowledge that the Bruins were planning to release Raycroft that off-season if they were unable to find a trading partner. That would have allowed Toronto to have signed their man without giving up a future star.
It has also since been discovered that the Bruins would have been willing to make the deal for Pogge instead of Rask. As it turned out, Peter Chiarelli, who had one month of experience as the general manager, fleeced the Leafs.
Raycroft lasted just two seasons with the Buds. He played 72 games in the 2006-07 season and 19 the following year. Then, two years to the day of that terrible trade, the Leafs placed Raycroft on waivers and later bought out the remainder of his contract.
Meanwhile, Pogge continued his development with the Leafs AHL affiliate, the Toronto Marlies. His AHL numbers were all underwhelming though he did get an opportunity in the NHL. He was trusted in net for seven games and even won one of those contests.
Rask has since gone on to play 488 more NHL games than Pogge. In that span, he has been named an NHL All-Star, won a Vezina Trophy, and a Stanley Cup. He also owns the Bruins franchise records for having played the most games as a goalie and earned the most franchise wins.