Of all the blockbuster deals that GMs and owners pitch, discuss, think about, propose, probably none has ever been more audacious then the one discussed, considered but ultimately declined:

The Edmonton Oilers of Gretzky, Messier and Kuri for the Maple Leafs, plus cash.

More here: http://www.vancouversun.com/sports/would+have+been+hockey+deal+time+Leaf...

Wayne Gretzky, Mark Messier, Jari Kurri and the rest of the young Edmonton Oilers nearly ended up in Toronto in a $50-million blockbuster swap of the two entire teams hatched by Harold Ballard, then-owner of the Maple Leafs, and Peter Pocklington, then-owner of the Edmonton Oilers, a new book claims.

"Ballard would move his fading Leafs to boomtown Edmonton, while Peter would bring his up-and-coming Oilers to Toronto — provided, of course, that he also wrote Ballard a cheque for $50 million."