Biggest trades Toronto Maple Leafs

Pittsburgh Penguins acquire Date Toronto Maple Leafs acquire
Phil Kessel
Tim Erixon
Tyler Biggs
2016 conditional 2nd round pick
July 1, 2015
Kasperi Kapanen
Scott Harrington
Nick Spaling
2016 conditional 1st round pick
2016 3rd round pick
Toronto Maple Leafs acquire Date Quebec Nordiques acquire
Garth Butcher
Mats Sundin
Todd Warriner
1994 1st round pick (#10-Nolan Baumgartner)
June 28, 1994
Wendel Clark
Sylvain Lefebvre
Landon Wilson
1994 1st round pick (#22-Jeff Kealty)
Toronto Maple Leafs acquire Date Calgary Flames acquire
Doug Gilmour
Jamie Macoun
Kent Manderville
Ric Nattress
Rick Wamsley
January 2, 1992
Craig Berube
Alexander Godynyuk
Gary Leeman
Michel Petit
Jeff Reese
Toronto Maple Leafs acquire Date Detroit Red Wings acquire
Norm Ullman
Floyd Smith
Paul Henderson
Doug Barrie
March 3, 1968
Garry Unger
Pete Stemkowski
Frank Mahovlich
rights to Carl Brewer
Toronto Maple Leafs acquire Date Chicago Blackhawks acquire
Max Bentley
Cy Thomas
November 2, 1947
Gus Bodnar
Ernie Dickens
Bob Goldham
Bud Poile
Gaye Stewart