The best and worst trade deadlines of the last four Maple Leafs GMs

Filipe Dimas
1 month ago
Brad Treliving is in the midst of going through his first ever trade deadline as General Manager of the Toronto Maple Leafs. As one of the most exciting days on the NHL calendar, it’s grown into a month-long event that many fans look forward to as their favourite team looks to either strengthen for the playoffs or sell assets as part of a rebuild.
Over the past 15 years, four different General Managers have helmed trade deadlines for the Maple Leafs before Treliving took over the role. Here are their best and worst performances surrounding the job-defining day.

Kyle Dubas

Years as Leafs GM: 2018-2023
Worst Deadline: 2021
Key Acquisitions: Nick Foligno, Riley Nash, David Rittich, Ben Hutton, Stefan Noesen
Key Losses: Alexander Barabanov, 1 First Round Pick (2021), 1 Third Round Pick (2022), 2 Fourth Round Picks (2021, 2022), 1 5th Round Pick (2022), 1 Sixth Round Pick (2022)
In April of 2021, Kyle Dubas traded away nearly an entire draft class worth of assets, sending away six total picks, including that year’s first rounder, to acquire a handful of depth pieces headlined by Columbus Blue Jackets captain Nick Foligno. 
None of the acquisitions would go on to do anything of note for the Maple Leafs, with all four skaters combining for a total of 12 regular season games and four points for the Toronto Maple Leafs. That statistic is made even worse when you consider that Alexander Barabanov would go on to score 7 points in 9 games that season, nearly doubling the combined production of every single player that Toronto acquired.
Despite the high price paid at the deadline, the Maple Leafs would still go on to lose in the first round with only six total playoff games and a single point being registered by all five of the acquired players. A year later, every single one of those acquisitions were on a different team, and Kyle Dubas had nothing to show for it while Barabanov would remain with the Sharks, scoring at an over 45 point pace each of the next two seasons.
Best Deadline: 2023
Key Acquisitions: Ryan O’Rielly, Noel Acciari, Jake McCabe, Luke Schenn, Sam Lafferty, Erik Gustaffson, Radim Zohorna, 1 First Round Round Pick (2023), 1 Third Round Pick (2024), 2 Fifth Round Picks (2024, 2025)
Key Losses: Rasmus Sandin, Pierre Engvall, Dryden Hunt, 2 First Round Picks (2023, 2025), 2 Second Round Picks (2024, 2026), 2 Third Round Pick (2023, 2023), 1 4th Round Pick (2025)
This was a fascinating trade deadline for Kyle Dubas, because in the moment it felt more like a retool than a full buying deadline. It’s rare that a contending team acquires a first rounder at the deadline, but that’s exactly what happened when Dubas shipped away Rasmus Sandin for a first round pick to make room on the blueline and salary cap for the new acquisitions.
After years of fans arguing the team needed more size and toughness, the team went out and got exactly that – adding Ryan O’Rielly, Jake McCabe and Luke Schenn to bolster their ability to hit and grind out opponents while solidifying defensive responsibility at the back end and down the middle.
The moves would pay off in part, with Toronto finally making it out of the first round for the first time in nearly two decades. Jake McCabe would remain on the roster, continuing to be a key part of the defense, while the Leafs used the acquired first round pick to draft Easton Cowan, who at the time of publishing has developed into one of the OHL’s top performers and the Maple Leafs’ number one prospect.

Lou Lamoriello

Years as Leafs GM: 2015-2018
Worst Deadline: 2018
Key Acquisitions: Tomas Plekanec, 1 Fourth Round Pick (2019), 1 Seventh Round Pick (2020)
Key Losses: 1 Second Round Pick (2018), Eric Fehr, Nikita Soshnikov
Unlike Kyle Dubas, Lou Lamoriello rarely made a splash at the trade deadline. In his defense, the Leafs weren’t quite contenders yet at the time, so trading big pieces for a playoff push rarely seemed like the move.

Even with that in mind, 2018s trade deadline stands out as an odd one. The team was on the upswing and looking for some veteran help to give an extra spark to a team of talented players on their rookie deals. The big acquisition? Tomas Plekanec. By no means was Plekanec bad for Toronto. Despite only managing two assists during the regular season, he was a surprising contributor in the playoffs at both ends of the ice. But the move seemed like a move just for the sake of making moves, and considering that Toronto took Boston to seven games that series, fans were left wondering if the Leafs could have made a deep run and avoided the playoff chokers title if Lamoriello had made a bigger splash.
Best Deadline: 2016
Key Acquisitions: Colin Greening, Milan Michalek, Jared Cowen, Tobias Lindberg, Daniel Winnick, Ben Smith, Alex Stalock, Raffi Torres, 4 Second Round Picks (2016, 2017, 2017, 2018), 1 Third Round Pick (2018), 1 Fourth Round Pick (2016),
Key Losses: Dion Phaneuf, Matt Frattin, Shawn Matthias, Roman Polak, Nick Spaling, James Reimer, Daniel Winnick, 1 Fifth Round Pick (2016)
Despite acquiring four second round picks, the real success of Lou Lamoriello’s 2016 trade deadline was making Toronto bad enough that they successfully finished last place to win the Auston Matthews lottery.
The month started off with a bang, with Toronto trading their captain Dion Phaneuf to Provincial rival Ottawa, and then the fire sale only continued to go on with contributing forwards, defenceman, and even the starting goalie all shipped out the door to ensure the team finishes in last place. It was an excellent way for Lou to navigate his first trade deadline as Toronto’s General Manager, and the team is still reaping the rewards to this day.

Dave Nonis

Years as Leafs GM: 2013-2015
Worst Deadline: 2014
Key Acquisitions: N/A
Key Losses: N/A
It’s not confirmed whether Dave Nonis was on vacation in the month leading up to March 5, 2014, but he sure seemed to behave like he was. The Toronto Maple Leafs didn’t make a single trade in the weeks leading up to 2014’s deadline, with the only move of note all season was acquiring Tim Gleason for John Michael-Liles back on January 1st. 
With the team having made a surprise playoff appearance the previous season, nearly beating the Boston Bruins in Game 7 before the infamous collapse – the Maple Leafs seemed to be unsure whether they were a piece away from being contenders, or just pretenders who got lucky in a lockout shortened season. The result? Standing pat and letting the NHL evolve around them.
Best Deadline: 2015
Key Acquisitions: Nathan Horton, Brendan Leipsic, Joakim Lindstron, Eric Brewer, TJ Brennan, Zach Sill, 1 First Round Pick (2015), 1 Second Round Pick (2016), 1 Fourth Round Pick (2015), 1 Fifth Round Pick (2015), 1 Sixth Round Pick (2016)
Key Losses: David Clarkson, Cody Franson, Mike Santorelli, Daniel Winnik, Spencer Abbott, Koribian Holzer
Despite acquiring five total draft picks, including a first and a second for mostly spare parts, the best move of the entire deadline was the Leafs ridding themselves of David Clarkson’s contract with no salary retained. Nonis seemed to finally be on cleanup duty, and allowed other teams to use Toronto’s wealth as a dumping ground for bad contracts, picking up the uninsured Nathan Horton deal and placing him on LTIR while also acquiring Eric Brewer and Olli Jokinen (who was later flipped for a late draft pick) from teams looking to make space on their rosters.
Unfortunately for Nonis, despite the excellent performance at 2015’s deadline, he was fired just over a month later and replaced with Lou Lamoriello.

Brian Burke

Years as Leafs GM: 2008-2013
Worst Deadline: 2012
Key Acquisitions: Mark Fraser, Carter Ashton
Key Losses: Dale Mitchell, Keith Aulie
The worst thing that a sports franchise can do is be stuck in limbo. Hovering around the middle without a direction on whether they’re buyers or sellers, and that’s exactly what the Toronto Maple Leafs looked like in 2012 under Brian Burke.
The only two trades to occur around the deadline were a couple of meaningless swaps, Fraser for Mitchell and Ashton for Aulie. It’s no surprise that Burke was relieved of his duties less than a year later as even he seemed unconvinced on what the Maple Leafs’ identity was.
Best Deadline: 2011
Key Acquisitions: Joffrey Lupul, Jake Gardiner, Aaron Voros, 2 First Round Picks (2011, 2011), 1 Second Round Pick (2012), 1 Third Round Pick (2011), 1 Fourth Round Pick (2014), 1 Seventh Round Pick (2012)
Key Losses: Tomas Kaberle, Kris Versteeg, Francois Beauchemin, John Mitchell
What a difference a year makes. While the Leafs may have been directionless in 2012, they were clear sellers at the deadline with Brian Burke getting a king’s ransom in the month leading up to deadline day. Not only was Burke able to acquire multiple first round picks for Tomas Kaberle and Kris Versteeg, but he also added Joffrey Lupul and Jake Gardiner in a trade that sent Francois Beauchemin to Anaheim.
Lupul and Gardiner would go on to become top of the lineup players for the Maple Leafs over the next few years as the Maple Leafs finally seemed to be embracing a rebuild of sorts.

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