The most frustrating aspect of the Maple Leafs' past 43 years is their unwillingness to hang onto first round draft picks. Even in the era of the salary cap where every team desperately clings to their first round picks, the Leafs continue to flip them in questionable deals.
The Leafs own only 2 of the 1st round picks over the past decade. Almost all are playing in the NHL.
Year, Prospect, Rank
2011 - Traded to Boston for Phil Kessel
2010 - Traded (2) to Boston for Phil Kessel
2009 - Nazim Kadri (7)
2008 - Luke Schenn (5)
2007 – Traded (13) to San Jose for Vesa Toskala (used to pick Lars Ellers)
2006 – Jiri Tlusty (13) traded to Carolina for Philippe Paradis
2005 – Tuukka Rask (21) traded to Boston for Andrew Raycroft
2004 – Traded (19) to the Rangers for Brian Leetch (used to pick Lauri Korpikosk)
2003 – Traded (21) to San Jose for Owen Nolan (used to pick Mark Stuart)
2002 – Alex Steen (24) traded to St. Louis for Lee Stempniak
2001 – Carlos Colaiacovo (17) traded to St. Louis for Lee Stempniak
2000 – Brad Boyes (24) traded to San Jose for Owen Nolan
1999 – Luca Cereda (24)
1998 – Nik Antropov (10) traded to the Rangers for a 2nd round pick
1997 – Traded (4) to the Islanders for Wendel Clark (used to pick Roberto Luongo)
1996 – Traded (15) to Philadelphia for Dmitri Yushkevich (used to pick Dainius Zubrus)
1995 – Jeff Ware (15)
1994 – Alex Fichaud (16)
1993 - Kenny Jonsson (12) traded to the Islanders for Wendel Clark
1992 - Brandon Convery (8)
1991 - Traded (2) to the Islanders for Tom Kurvers (used to pick Scott Niedermayer)
1990 - Drake Berehowsky (10)
1989 - Scott Thornton (3), Rob Pearson (12), Steve Bancroft (21)
1988 - Scott Pearson (6)
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