3. Glen Sather
The trade: The Edmonton Oilers traded Wayne Gretzky, along with Marty McSorely and Mike Krushelnyski, to the Kings in exchange for Jimmy Carson, Martin Gelinas, three first-round picks, and $15 million. (1988)
The aftermath: Depending on what listicle you look at, this is rated as the worst trade ever to occur in the kingdom of hockey. No doubt because it is one of, if not the, most emotional trade to date. The fact that the Oilers won a Cup after the trade doesn’t even make a difference.
Canada’s greatest athlete and celebrity was shipped off to Hollywood, and Edmonton did not take it well. Like, Oilers’ GM Peter Pocklington received death threats because Oilers fans could not except it. It’s still a hot discussion topic whether or not the Gretzky trade was the first move in disassembling the unstoppable Oilers dynasty. Jari Kurri and Mark Messier departed just a couple seasons later, and others followed through the early ’90s.