Ed Olczyk started the 1990-91 season with the Toronto Maple Leafs, coming off seasons of 90 and 88 points for some pretty bad hockey teams. 18 games in, he was sent to Winnipeg along with Mark Osborne for Dave Ellett and Paul Fenton.
Initially, the trade looked like another Courtnall for Kordic-esque gaffe by questionable Leaf management of the era, especially after Olczyk scored in his first game for his new team, against the Leafs, no less. But, Ellett did end up being a key component in the Leafs’ run to the Conference Finals in 1993 and 1994, as did Osborne after he was dealt back to Toronto midway through 1991-92.
Interestingly enough, the next time Olczyk was traded, it was from the Jets to the New York Rangers for Kris King and Tie Domi, both future Leafs, both of whom were contributors to another strong Toronto playoff run in 1999.
The way the Leafs have been lately, maybe they should try trading him again and see what happens.