[1-11] [Bad Trades] [Bad Drafting] [Tradition?]

The NHL Amateur Entry Draft is well known to have a few surprises each year. Of course, when it comes to the First Round, the picks are usually well thought out and researched. USUALLY. Check out the atrocious first round draft history of the Leafs. It's no wonder they haven't even made the Stanley Cup Final since 1967.
| 1969 - Ernie Moser (9th overall) - could have had Ivan Boldirev (11th overall). | |
| 1973 - Bob Neely (10th overall) - could have had Rick Middleton (14th overall). | |
| 1974 - Jack Valiquette (13th overall) - could have had Dave Maloney (14th overall). | |
| 1977 - Trevor Johansen (12th overall) - could have had Mike Bossy (15th overall). | |
| 1981 - Jim Benning (6th overall) - could have had Grant Fuhr (8th overall). | |
| 1982 - Gary Nylund (3rd overall) - could have had Scott Stevens (5th overall). | |
| 1987 - Luke Richardson (7th overall) - could have had Joe Sakic (15th overall). | |
| 1988 - Scott Pearson (6th overall) - could have had Jeremy Roenick (8th overall). | |
| 1989 - Scott Thornton (3rd overall) - could have had Bill Guerin (5th overall). | |
| 1989 - Steve Bancroft (21st overall) - could have had Adam Foote (22nd overall). | |
| 1990 - Drake Berehowsky (10th overall) - could have had Keith Tkachuk (19th overall) | |
| 1992 - Brandon Convery (8th overall) - could have had Sergei Gonchar (14th overall) | |
| 1993 - Landon Wilson (19th overall) - could have had Saku Koivu (21st overall). | |
| 1994 - Eric Fichaud (16th overall) - could have had Dan Cloutier (26th overall). | |
| 1995 - Jeff Ware (15th overall) - could have had Petr Sykora (18th overall). | |
| 1998 - Nikolai Antropov (10th overall) - could have had Alex Tanguay (12th overall). | |
| 1999 - Luca Cereda (24th overall) - could have had Martin Havlat (26th overall). |