January 2nd, 1992: Toronto Maple Leafs GM Cliff Fletcher orchestrates the biggest trade in NHL history by hooking up with the Calgary Flames for a 10 player BLOCKBUSTER transaction with center Doug Gilmour as the centrepiece.
The full deal:
Leafs acquire Gilmour, Jamie Macoun, Kent Manderville, Ric Nattress and Rick Walmsley for Craig Berube, Alex Godynyuk, Gary Leeman, Michel Petit and Jeff Reese.
Wow… kudos if you can remember even half of those names off the top of your head. Of course, Gilmour would go on to become a legend with the Leafs, scoring 127 points and 111 points in his first full two seasons with the club. The man they call Killer was already a point-per-game player with the Flames that season, but took his game to another level with the Leafs, potting 15 goals and 49 points in 40 games with his new club.
Gilmour would go on to play six seasons with the Leafs before finishing out his career with the New Jersey Devils, Chicago Blackhawks, Buffalo Sabres and (GASP!) the Montreal Canadiens.