Top 5 Best Toronto Maple Leafs General Managers of All-Time

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Toronto Maple Leafs – Kyle Dubas and Brendan Shanahan at the draft (Photo by Bruce Bennett/Getty Images) /

The Toronto Maple Leafs General Manager position is one of the most decorated jobs in professional hockey and in over 100 years, just 17 men have been fortunate to have accepted that position.

The job of being the Toronto Maple Leafs General Manager (GM) has the same responsibilities as the other 30 teams in the National Hockey League. To quote the late, great Al Davis: “Just Win, Baby.”

Unfortunately winning is not as easy as that sounds. The NHL has never had so much parity, and if a GM doesn’t win in their first two years, the clock usually strikes midnight and they’re fired.

With that being said, of the 17 men who have been the Toronto MapleLeafs GM, only three of them have won a Stanley Cup, and the last GM to win (Punch Imlach) died in 1987, so it’s been a while.

Despite not winning a Stanley Cup since 1967, the Toronto Maple Leafs have seen a number of quality executives over the years, so let’s breakdown the top five most notable GM’s of all-time.

5. Brian Burke (November 29, 2008 – January 9, 2013)

Best Trade: Philadelphia Flyers trade James van Riemsdyk to Toronto for Luke Schenn

Worst Trade: Boston Bruins trade Phil Kessel to the Toronto for a 2010 first-round pick (Tyler Seguin), a 2010 second-round pick (Jared Knight) and a 2011 first-round pick (Dougie Hamilton).

Best FA Signing: Tyler Bozak signs a two-year $3 million contract

Worst FA Signing: Tim Connolly signs a two-year $9.5 million contract

Best Draft Pick: Morgan Rielly (2012 NHL Entry Draft, 5th overall)

Worst Draft Pick: Tyler Biggs (2011 NHL Entry Draft, 22nd overall)

Grade: C –

Final Thoughts: Burke was looked at to save the Leafs when he arrived. Unfortunately, his truculence style didn’t work out in Toronto.

TORONTO, ON-Toronto- Kyle Dubas (Rene Johnston/Toronto Star via Getty Images) /

4. Kyle Dubas (May 11, 2018 – Present)

Best Trade: LA Kings trade Jake Muzzin to Toronto for Carl Grundstrom, Sean Durzi, 1st Round Pick

Worst Trade: Carolina Hurricanes trade 6th Round Pick to Toronto for Patrick Marleau, 2020 conditional 1st Round Pick, 2020 7th Round Pick

Best FA Signing: John Tavares signs a seven-year $77 million contract

Worst FA Signing: Jordan Subban signs 1 year entry level contract.

Best Draft Pick: Rasmus Sandin (2018 NHL Entry Draft, 29th overall)

Worst Draft Pick: N/A (Too early to tell)

Grade: B –

Final Thoughts: In a short-time, Dubas has already had his ups and downs. However, the ability to sign John Tavares alone qualifies him as a top-five notable GM of all-time.

3. Pat Quinn (July 15, 1999 – August 29, 2003)

Best Trade: Tampa Bay Lightning trade Darcy Tucker, 2000 4th Round pick, future considerations to Toronto for Mike Johnson, Marek Posmyk, 2000 5th Round pick, 2000 6th Round pick and future considerations.

Worst Trade: Montreal Canadiens trade Doug Gilmour to Toronto for 2003 6th Round pick (Mark Flood)

Best FA Signing: Alexander Mogilny signs a four-year $22 million contract

Worst FA Signing: Syl Apps III signs to entry level contract

Best Draft Pick: Alexander Steen (2002 NHL Entry Draft, 24th overall)

Worst Draft Pick: John Doherty (2003 NHL Entry Draft, 57th overall)

Grade: B

Final Thoughts: Pat Quinn was probably a better coach than GM, but in four seasons as the GM, Quinn made the playoffs each year, including an Eastern Conference Finals appearance.

VANCOUVER, BRITISH COLUMBIA – JUNE 22: Kyle Dubas (Photo by Jeff Vinnick/NHLI via Getty Images) /

2. Lou Lamoriello (July 23, 2015 – April 30, 2018)

Best Trade: Anaheim Ducks trade Frederik Andersento Toronto for 2016 1st Round Draft pick and 2017 2nd Round Draft pick.

Worst Trade: Chicago trades Jeremy Morin to Toronto for Richard Panik

Best FA Signing: Patrick Marleau signs a three year $18.75 million contract

Worst FA Signing: Matt Martin signs a four year $10 million contract

Best Draft Pick: Auston Matthews (2016 NHL Entry Draft, 1st overall)

Worst Draft Pick: Jack Walker (2016 NHL Entry Draft, 152nd overall)

Grade: A

Final Thoughts: There is no GM that did more with less. Lamoriello evaluated a team in a terrible situation, hit the refresh button and executed a perfect rebuild to help the Leafs make the playoffs for the first time since 2004.

1. Conn Smythe (February 14, 1927 – September 1, 1957)

Best Trade: Detroit trades Turk Broda to Toronto for $8K cash

Worst Trade: Detroit trades future considerations (cash)to Toronto for Charlie Conacher

Grade: A +

Next. Why the Leafs Are So Much Better Than the Media Portrays Them. dark

Final Thoughts: In 30 years as the architect of the Toronto Maple Leafs, Smythe made the playoffs 25 times, with 13 Stanley Cup Final appearances, including 7 championships.

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