Five Worst Maple Leafs Trades Of Salary Cap Era

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Jan 9, 2015; Edmonton, Alberta, CAN; Chicago Blackhawks forward Brandon Saad (20) scores a first period goal against the Edmonton Oilers at Rexall Place. Mandatory Credit: Perry Nelson-USA TODAY Sports

September 5, 2009 – GM Brian Burke

The Maple Leafs dealt away the pick that would turn into Brandon Saad in this deal. Saad had 19 goals and 28 assists for 47 points last year for Chicago and is off to another good season with 12 points through the first 18 games this year.

Saad was part of the depth group that led Chicago to a Stanley Cup in 2013.

The pick that Toronto acquired would be included in the trade that brought Phil Kessel to Toronto, with Jared Knight being drafted by the Boston Bruins.

Next: #3: Roman Josi