The Worst Trade in Toronto Maple Leafs History

There are a lot of candidates for the worst trade in the history of Toronto Maple Leafs.

Depending on your age, you might think the Worst Trade in Toronto Maple Leafs history is the one of the ones where they traded Randy Carlyle, Darryl Sittler, Lanny McDonald, Rich Vaive, or Russ Courtnall.

It’s subjective, and if you like the Leafs, you have a rich history of garbage roster moves to choose from.  Maybe you deeply regret the series of moves that prevented the Leafs from having a chance at Eric Lindros.  Maybe it’s something more recent like the one that cost the Leafs a chance at Tyler Seguin and Dougie Hamilton.

God knows you’ve got a lot of choices.

For me, the worst trade in the history of the Toronto Maple Leafs is the one where they re-acquired fan favorite Wendel Clark.

The Worst Trade Ever


Wendel Clark is one of the best players in the history of the Leafs, but the decision by Cliff Fletcher to re-acquire him for sentimental reasons back in 1996 was so misguided that Peter Chiarelli probably makes fun of it.

On March 13 1996 the Toronto Maple Leafs acquired Wendel Clark, Mathieu Schneider and DJ Smith from the New York Islanders in exchange for Kenny Jonsson, Darby Hendrickson, Sean Haggerty and a first round pick.

In 1994, the Leafs traded Wendel Clark to the Nordiques for Mats Sundin, in perhaps the greatest trade in NHL history.  Clark played a single season for the Nordiques, then he joined the Islanders for a few months before going back to the Leafs.

All things aside, Fletcher should have known better than to make this trade since it had been a decade since Clark had hit the 70 game mark in a season.

The Leafs entered the season with Sundin and Gilmour, but they were terrible. Eventually they fired coach Pat Burns and the trade for Clark and Schneider was a desperate move by Fletcher to save the season.

They eventually did make the playoffs, but the cost was enormous.  Clark was 30, but had the body of a 98 year old. Schneider was 27 and a bona-fide #1 defenseman, so he was probably the main target of the trade.

Terrible Trade!

The first major problem with this trade was that the Leafs didn’t recognize that they were a veteran team on the downswing – even though at the time they were barely a playoff team and had already fired their coach – and so trading futures for players who weren’t ever going to get any better was ill advised.

Predictably, the Leafs lost in the first round after acquiring Clark, then they had two more season of total crap where they missed the playoffs twice, before Clark, Schneider and Cliff Fletcher were all sent packing.

Kenny Jonsson went on to play 600 games for the Islanders, as a solid #2.  That might not sound like much, but other than Tomas Kaberle, that would make him far and away the best defenseman the Leafs had in this period.

That’s bad enough, but the real kicker is the player that the Islanders would select with the Leafs draft pick: Robert Luongo.

Luongo turned out to be one of the best goalies in the history of the NHL and is a sure-fire first ballot hall of famer.  Had the Leafs selected him, he’d likely be in the conversation with Mats Sundin for best player in team history.

A team built around Mats Sundin, Tomas Kaberle, Kenny Jonsson and Robert Luongo would probably have won at least one Stanley Cup.  Maybe more.

And for that reason, I declare this the worst trade in Toronto Maple Leafs history.