Yeah it doesn't get much worse than giving Phaneuf 7/49.
In baseball terms I want to say that that's the rough equivalent of, say, the Josh Hamilton deal (or something like that).
So many bad trades in recent Leafs history. As a Boston fan my personal favourite has to be the Rask deal. Used to be the Kessel trade but then the Bruins had to ruin everything by trading Seguin for junk....
This is another personal fave though:
2011 draft, Toronto trades picks #30 and #39 for pick #22. They pick Tyler Biggs at #22, a guy described as having 3rd line upside who currently has like 2 points for the Marlies. Anaheim picks Rickard Rakell (hey, at least he's in the NHL (I think) and his name is cool) and John Gibson super-stud with those two picks.