Maple Leafs history of deadline trades has yielded big names, but no Stanley Cups

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Joel Edmundson will hardly rock the Richter Scale of Maple Leaf deadline deals.

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One more day remains to do something bigger, but with their team fairly set and another two draft picks out the door to secure Edmundson on Thursday from Washington, there’s little for Brad Treliving to work with other than swap valued roster players and prospects.

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With Edmundson and Ilya Lyubushkin acquired earlier, the Leafs look better on defence approaching playoffs, but depth for the bottom-six forwards is an issue approaching the deadline at 3 p.m. on Friday.

Here are some late-season and deadline trades noteworthy for Toronto since NHL expansion in 1967-68. Despite the best of intentions by the listed general managers, none of the moves helped the Leafs back into the Stanley Cup final.

March 3, 1968

TRADE: F Paul Henderson, F Floyd Smith and F Norm Ullman from Detroit for F Frank Mahovlich, F Peter Stemkowski, F Garry Unger and the rights to D Carl Brewer

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GENERAL MANAGER: Punch Imlach

IMPACT: This blockbuster of its time broke the hearts of Toronto fans, who had worshipped the Big M, the four-time Cup winner who often feuded with Imlach. Stemkowski was also on the ’67 Cup team, but while Ullman and Henderson would have great impact in coming years and the Leafs got an immediate bump of a 8-4-1 record after the trade, they missed the playoffs.

March 3, 1973

TRADE: A first-round pick (D Ian Turnbull) and future considerations (G Ed Johnston) for G Jacques Plante and Toronto’s first-round pick (F Doug Gibson).

GM: Jim Gregory

IMPACT: Leafs weren’t making the playoffs in ‘73, but benefitted from the swap of picks in adding Turnbull to a growing mid-70s contender.

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March 13, 1978

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TRADE: F Dan Maloney and a second-round pick (D Craig Muni) from Detroit for F Errol Thompson, two first-round picks and a second.

GM: Jim Gregory

IMPACT: Going all-in on coach Roger Neilson’s physical X’s and O’s got the Leafs through a seven-game series for the first time in a decade, but the Montreal Canadiens dynasty would deny them in back-to-back springs. Luckily, the lost high picks didn’t haunt the Leafs.

March 9, 1982

TRADES: F Walt Poddubny and F Phil Drouillard from Edmonton for F Laurie Boschman; F Miroslav Frycer and a seventh-rounder from Quebec for F Wilf Paiement; F/D Jim Korn from Detroit for a fourth- and fifth-rounder.

GM: Gerry McNamara

IMPACT: Leafs went 8-6 after the deal and Frycer added to the strong Czechoslovakian vibe, tying for the lead in playoff points. But the Leafs won just once in a best-off-five against the Minnesota North Stars.

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March 10, 1992

TRADES: F/D Ken Baumgartner and F Dave McLlwain from the Islanders for F Daniel Marois and F Claude Loiselle; F Mark Osborne from Winnipeg for F Lucien DeBlois.

GM: Cliff Fletcher

IMPACT: The Leafs were out of the playoffs, but the ‘Silver Fox’ lined up important pieces for incoming coach Pat Burns to complement Doug Gilmour, who was acquired earlier in the year in a 10-player swap with Calgary.

March 21, 1994

TRADE: F Mike Gartner from the New York Rangers for F Glenn Anderson, D Scott Malone and a fourth-rounder.

GM: Cliff Fletcher

IMPACT: Gartner had 11 goals in 29 playoff games the next three years.

April 6-7, 1995

TRADES: F Benoit Hogue, a third- and fifth-round pick from the Islanders for G Eric Fichaud; F Tie Domi from Winnipeg for F Mike Eastwood and a third-round pick; F Paul DiPietro from Montreal for a fourth-round pick; D Grant Jennings from Pittsburgh for D Drake Berehowsky.

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GM: Cliff Fletcher

IMPACT: After winning four of six series the previous two years and getting to the Western Conference final twice, this chemistry experiment after a lockout-delayed season faltered after the Leafs won the first two games of their series against Chicago.

March 13, 1996

TRADE: F Wendel Clark, D Mathieu Schneider and D D.J. Smith for D Kenny Jonsson, F Darby Hendrickson D Sean Haggerty and a first-round pick (G Roberto Luongo).

GM: Cliff Fletcher

IMPACT: Neither the much-desired return of Clark, an overhauled roster nor the firing of Burns could get the Leafs past St. Louis in the first round. Did we mention the Hall of Fame stopper they might have had?

Feb. 25, 1997

TRADE: D Jason Smith, F Steve Sullivan and F Alyn McCauley from New Jersey for D Dave Ellett, Doug Gilmour and a third-round pick.

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GM: Cliff Fletcher

IMPACT: Notable names involved and the end of the Gilmour comet, but Leafs were too far back in the playoff race.

March 5, 9, 11, 2003

TRADES: F Owen Nolan from San Jose for McCauley, F Brad Boyes and a first-round pick (D Mark Stuart); D Glen Wesley from Carolina for a second-rounder; D Phil Housley from Chicago for future considerations, Gilmour from Montreal for a sixth-rounder.

GM: Pat Quinn

IMPACT: Gilmour played one period before a career-ending injury and, while the Leafs lost just once in regulation down the stretch, the costly makeover for a projected long playoff run ended in a first-round loss to the Flyers. The luck of the Irish evaded Quinn and Nolan, who was hurt and managed just two points. Other than Alex Mogilny’s five goals, incumbents and newcomers didn’t produce.

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March 3, 9 2004

TRADES: D Brian Leetch from the New York Rangers for a first-rounder (Chris Chucko), a second-rounder, D Max Kondratiev and F Jarko Immonen; F Ron Francis from Carolina for a fourth-rounder.

GM: Pat Quinn

IMPACT: Surviving a seven-game series with Ottawa, the big-name Leafs struggled to score next round versus the Flyers and fell in six games.

Feb. 27, 2007

TRADE: F Yanic Perreault and a fifth-rounder from Phoenix for D Brendan Bell and a second-rounder.

GM: John Ferguson Jr.

IMPACT: This was not a big deal as the Leafs got a good faceoff man in a year they were out of the race. But the pick wound up in Nashville’s hands, which used it on future Norris Trophy winner Roman Josi.

March 4, 2009

TRADES: A second-rounder (F Kenny Ryan) and conditional pick from the Rangers for F Nik Antropov; a second-rounder from Buffalo (D Jesse Blacker) for F Dominic Moore; G Olaf Kolzig, D Jamie Heward and D Andy Rogers from Tampa Bay for D Richard Petiot.

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GM: Brian Burke

IMPACT: The mighty had fallen, in a series of salary dumps and taking on expiring contracts as a favour to the Lightning.

April 3, 2013

TRADE: F Ryan O’Byrne from Colorado for a fourth rounder.

GM: Dave Nonis

IMPACT: Back in the playoffs at last, Leafs added some size, but the 6-foot-5 O’Byrne couldn’t alter their Game 7 collapse in Boston and never played in the NHL again.

Feb. 27, 2017

TRADE: F Brian Boyle from Tampa Bay for F Byron Froese and a second-rounder.

GM: Lou Lamoriello

IMPACT: With the Shanaplan off to a fast start, Lamoriello ‘rewarded’ the young Leafs in their first series with a veteran pick up. Boyle had a couple of assists in a gritty loss to Washington.

Feb. 25, 2018

TRADE: F Tomas Plekanec and F Kyle Baun from Montreal for F Kirby Rychel, D Rinat Valiev and a second-rounder.

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GM: Lou Lamoriello

IMPACT: Plekanec’s heart appeared to still be in Habs land, but the premise of the trade was good.

April 9-12, 2021

TRADES: F Nick Foligno from Columbus for a first- and fourth-round pick; F Riley Nash from Colorado for a seven-rounder; G David Rittich from Calgary for a third-rounder; D Ben Hutton from Anaheim for a fifth-rounder, F Antti Suomela from San Jose for F Alexander Barbarov.

GM: Kyle Dubas

IMPACT: Foligno was hurt after one assist in four playoff games, contributing to Montreal’s upset after the Leafs ruled the North in the COVID season. Nash got in a couple of games.

March 20, 2022

TRADE: D Mark Giordano and F Colin Blackwell from Seattle for two second-round picks and a third.

GM: Kyle Dubas

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IMPACT: Giordano eventually helped the Leafs to their first series win in 19 years and, at age 40, is still in their picture, despite currently being concussed.

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Feb. 27-28, 2023

TRADES: D Jake McCabe, F Sam Lafferty and a conditional fifth-rounder from Chicago for a conditional first-round pick, a second-rounder, F Joey Anderson and F Pavel Gogolev; D Luke Schenn from Vancouver for a third-rounder: D Erik Gustafsson and a first-rounder from Washington for D Rasmus Sandin; a third-rounder from the Islanders for F Pierre Engvall.

GM: Kyle Dubas

IMPACT: The Leafs got by the Lightning and McCabe has become a more integral part of the blueline than the skill-oriented Sandin was. However, Lafferty was allowed to slip away in the summer and restoring the top and bottom-six balance has proven hard for Treliving.

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