Except the Leafs are getting 2 draft picks in return, so they are trying to make up for the Kessel trade, one of the worst in NHL history.
On October 16, 1989 the Toronto Maple Leafs traded their 3rd overall pick to the
New Jersey Devils for Tom Kurvers. The 3rd pick ended up being Scott Niedermayer.
This says hi.
On August 9, 1988 the Edmonton Oilers trade Wayne Gretzky, Mike Krushelnyski and Marty McSorley to the Los Angeles Kings for Jimmy Carson, Martin Gelinas, a 1st round pick in 1989 (Jason Miller), 1st round pick in 1991 (Martin Rucinsky), a 1st round pick in 1993 (Nick Stajduhar) and about 15 million in cash.
So does this.
On June 30, 1992 the Philadelphia Flyers traded Chris Simon, Mike Ricci, Kerry Huffman, Ron Hextall, Steve Duchesne, Peter Forsberg, 1st round pick in 1993 (Adam Deadmarsh), 1st round pick in 1994 (Wade Belak), future considerations and cash to the Quebec Nordiques for Eric Lindros
This.
On June 23, 2001 the New York Islander trade Bill Muckalt, Zdeno Chara and a 1st round pick (turned out to be Jason Spezza) to the Ottawa Senators for Alexei Yashin
And espescially this.
Sure Kessel hasn't produced yet but he is young and can easily produce 30+ goals a year. Tyler Seguin has yet to prove himself, the list of 1st round flameouts is ridiculously long. At the moment the trade hasn't worked out well but in no way does it deserve to be mentioned anyway near the ones listed above.
Further, trades should not be judged based on how they turned out on future years. In the Cam Neely for Barry Pederson trade, the Canucks were acquiring a center who (iirc) had scored 126 goals over the past 5 years in exchange for a player who was undersized and appeared to lack upside. Now obviously Pederson flamed out while Neely became one of the games greats but at the time it was not at all a bad trade for the Canucks.