The trade deadline is less than two weeks away, and most of the speculation has the Maple Leafs being relatively quiet. They’ll probably make a depth move or two, and could deal a pending UFA, but anything bigger than that would come as a surprise.
That’s likely the right move for the franchise, even if it would no doubt draw criticism from some fans who want to see the team swing for the fences. Trade deadlines are always more fun when your team goes big.
Then again, big deals aren’t always the best deals, and Leaf fans know that well. The team has had, to put it generously, a mixed history when it comes to the trade deadline. Today, let’s revisit that history with a quick ranking of every Leafs trade deadline of the last 25 seasons.
We’ll define “the deadline” as the two weeks leading up to the last day of trading, and our 25-season cutoff will take us back to 1991. Why then? Because 25 is a workable number, it essentially covers the time where the NHL’s trade deadline was a big deal, and it happens to coincide with the start of the Cliff Fletcher era. Also, it avoids having to mention the Harold Ballard era, as per my therapist’s recommendations.
We’ll rank our way down from worst to best. And we’ll start with one of the low points in recent franchise history.
25. – 2008
The deals: On the verge of missing the playoffs for a then franchise-record third straight year, the Leafs fire John Ferguson Jr. and head to the deadline firmly in fire-sale mode. Interim general manager Cliff Fletcher moves Wade Belak, Chad Kilger and Hal Gill, all for picks.
The outcome: None of the picks end up helping the Leafs, but that’s not the reason this year rates dead last on our list. No, that has more to do with who wasn’t traded – namely, the fabled Muskoka Five, the group of veterans led by Mats Sundin who decide en masse not to waive their no-trade clauses.
Fletcher is clearly furious, but his hands are tied. A golden opportunity to rebuild slips away – Tomas Kaberle would have landed the Leafs a young Jeff Carter – and the team doesn’t fully recover for years.
24. – 1997
The deals: With the Leafs on the verge of missing the playoffs for the first time in five years, Fletcher goes into sell mode. He’d already moved Doug Gilmour to the Devils a month earlier. On deadline day he sends Kirk Muller to the Panthers for prospect Jason Podollan, and Larry Murphy to the Red Wings for future considerations.
The outcome: Podollan never amounts to anything. But it’s the Murphy deal that stands out. The future considerations end up being nothing at all – Fletcher literally hands a future Hall-of-Famer over to the Red Wings as a freebie. Murphy puts in four good years in Detroit, helping them win two Cups, and the move stands as one of the most lopsided trade deadline deals in league history.
23. – 2003
The deals: In what turns out to be his last year as general manager, Pat Quinn goes all-in. He makes the Owen Nolan blockbuster, and trades draft picks for veterans Glen Wesley, Phil Housley and a returning Doug Gilmour.
The outcome: You can appreciate the effort, but in hindsight none of the moves work. Nolan gets hurt and later has a falling out with the franchise, and acquiring him costs the Leafs a first-round pick in the ridiculously stacked 2003 draft. Wesley and Housley don’t add much. And the worst of the bunch is Gilmour; his big return lasts just five shifts before his career ends on this play:
22. – 2001
The deals: In their only deadline deal, the contending Leafs trade Adam Mair and a second-round pick to the Kings for Aki Berg.
The outcome: Berg struggles badly and quickly becomes a whipping boy in Toronto. The deal somehow gets even worse when the Kings turn the second-round pick into Mike Cammalleri.
21. – 1996
The deals: With Pat Burns fired and the Leafs fading, Fletcher starts blowing things up by sending Ken Baumgartner to the Ducks and Dave Andreychuk to the Devils. But the big news is the blockbuster that brings Wendel Clark back to Toronto.
The outcome: The Clark trade ends up being widely viewed as a disaster; the Leafs give up a young Kenny Jonsson and a 1997 draft pick that turns into Roberto Luongo. It’s the deal that leads to Fletcher’s infamous “draft schmaft” comment and puts the first serious dent in his Toronto reputation. Still, if you were a Leafs fan back then, you can’t deny that Clark’s return to the Gardens was one of the decade’s best moments.
20. – 2013
The deals: In the first year of the Dave Nonis era, the Leafs only make one move, adding Ryan O’Byrne for a pick.
The outcome: You would have thought the playoff-bound Leafs would be trading for multiple assets, but as it turns out, it was for one.