Looking back at Kyle Dubas’ biggest moves as Maple Leafs GM

Gord Stellick and Nick Kypreos discuss if Kyle Dubas' negotiating tactics with Brendan Shanahan and the Toronto Maple Leafs ended up being the breaking point for a potential extension falling through.

The Kyle Dubas era has officially come to an end in Toronto with Friday’s news that the Maple Leafs will not be renewing his contract after five years as general manager.

It’s an era defined by remarkable regular-season results, but also an inability to translate that into playoff wins come springtime. It’s an era that opened with the statement-making signing of John Tavares on the free agent market and now closes with questions about whether we’ve seen the last of the core four Dubas locked up and so vehemently backed for five straight attempts at post-season success.

While the on-ice product underwent significant changes under his leadership, the Dubas era was also one of great stability in the front office and behind the bench. He implemented a strong culture, stated clearly the organization’s stance on important social issues at times when hockey’s voices fell silent, introduced revamped hiring processes that welcomed a more diverse pool of candidates, and made just a single head coaching change over his tenure. Even Dubas’ own promotion to the top job in May 2018 was a smooth transition, part of the carefully laid plan spelled out by president Brendan Shanahan, who’d made no secret of his intention to have Dubas learn under Lou Lamoriello as assistant GM for four years before taking the reins.

But while Dubas’ fingerprints are all over this organization dating back to his joining the front office in 2014, the roster he assembled over his five years as GM tells the story of how he’s led this historic franchise — and how this era will ultimately be measured and remembered, too.

Over the course of his five years and eight days leading the Maple Leafs, Dubas negotiated 204 signings (doling out nearly $628 million, according to CapFriendly), oversaw the drafting of 44 players, and made 71 trades.

The Maple Leafs made the playoffs every year of Dubas’ five seasons at the helm, and this spring finally found their footing in the first round as they put away the Tampa Bay Lighting and won a playoff series for the first time in nearly two decades.

Landing John Tavares in free agency

After four years as assistant GM, Dubas wasted no time making a big splash — his biggest, in fact, over his entire tenure — just two months into his time in charge when he caught the biggest fish in free agency with the signing of then-UFA John Tavares on July 1, 2018.

The seven-year, $77-million deal solidified Toronto’s status as contenders, its young core now suddenly known as the “core four” on whom the franchise’s Stanley Cup hopes weighed… but would Dubas be able to keep the quad together?

‘We can, and we will’: Locking up the core four

If the signing of the league’s hottest free agent in recent memory didn’t state it loudly enough, Dubas made his mission crystal clear just a few days later with five words that would ultimately define his Toronto tenure:

“We can, and we will.”

When he spoke those words in early July 2018, the ink was still drying on Tavares’ massive deal and questions were swirling as to whether the GM could really lock up his young core around the newest centreman (and future captain). Mitch Marner and Auston Matthews were at the time eligible for their first real contracts, one year still remaining on each player’s entry-level deal, while negotiations with William Nylander were still in their early days of what would turn out to be a very long and tumultuous series of talks.

He made good on his declaration, signing Nylander to a six-year deal the following December worth $45 million ($6.96-million cap hit through 2023-24), squeezing in the contract just ahead of the signing deadline. Two months later, he locked up Auston Matthews to a five-year, $58.195 million contract ($11.634-million cap hit through 2023-24) followed by a six-year, $65.408-million deal ($10.893M cap hit through 2024-25) for Mitch Marner in September 2019.

Once his core-four forwards were locked up, Dubas also made sure to lock in cornerstone defenceman Morgan Rielly in October 2021 (eight years, $60-million, $7.5-millin cap hit).

Moving on from Nazem Kadri

Bringing in Tavares and locking up his top four forwards meant making some difficult decisions about those who saw themselves pushed down the lineup — and exactly a year after signing Tavares, Dubas pulled off his first blockbuster trade by sending Nazem Kadri to Colorado in exchange for Tyson Barrie and Alexander Kerfoot.

While the Barrie experience ultimately didn’t gel so well in Toronto, the defence-focused transaction showed Dubas’ desire to shore up his blue line after it proved itself to once again be a weakness on the roster. The trade also opened up a need to replace the sandpaper and skill Kadri had brought to the lineup — not to mention, his extremely team-friendly deal.

Bargain hunting & riding the goalie carousel

Out of necessity and out of a seemingly natural knack for seeking out underrated skill and helping it grow, Dubas quickly earned a reputation as a GM ready and willing to take a chance on underperforming players — at the right price, of course — and help revive their careers.

Take Michael Bunting, for example. Bunting went from having 14 career points in 26 games in Arizona in two seasons to hitting back-to-back 23-goal seasons upon signing a two-year, $1.9-million deal in Toronto in July 2021.

Before that, it was Ilya Mikheyev who enjoyed breakout success upon signing a one-year deal worth $925,000 followed by a two-year pact ($1.645 million per) in October 2020. His career-best 21 goals in 2021-22 earned him a solid showing on the free agency market, resulting in a four-year, $19-million contract with the Canucks.

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Dubas’ willingness to take a chance on players extended to the crease, too, where the Maple Leafs saw a near-constant rotation during the second half of Dubas’ tenure. His acquisition of Jack Campbell from the Kings at the 2020 trade deadline was intended to solve the Maple Leafs’ backup goalie woes and instead resulted in Toronto having a new No. 1 netminder.

After letting Frederik Andersen walk in 2021, Dubas turned to the tandem of Petr Mrazek and Campbell, with the latter taking over the starter’s role and outperforming all expectations while playing on the $1.65-million AAV he’d signed with the Kings. Campbell converted his success in 2022 into a big-money deal in Edmonton, while Dubas once again got creative in Toronto’s crease last summer by bringing in Matt Murray from Ottawa and reviving Ilya Samsonov after he stumbled with Washington. The one-year signing of Samsonov for $1.8 million was a low-risk financial bet that mostly paid off, but Toronto’s goaltending struggles persisted in the playoffs — and will now likely be a top priority of Dubas’ successor.

Dubas’ bargain hunting also extended to players nearing the ends of their careers. While Lamoriello’s signing of Patrick Marleau ultimately fell short of expectations, prompting Dubas to deal away a first-rounder to shed Marleau’s heavy cap hit in 2019, Dubas did understand the value in bringing in veteran players on good-value deals. Jason Spezza, Joe Thornton, Wayne Simmonds, and Giordano have all signed for minimum deals during Dubas’ time, with Spezza going on to serve alongside him in the front office.

Firing Babcock, hiring Keefe

Dubas made just one head coaching change in his five years at the helm. He was part of the front office that hired Mike Babcock in 2016 and inherited the veteran bench boss upon his promotion to GM two years later. Babcock remained in place when Dubas took over until November 2019 when, 18 months into his job as GM, Dubas made his one and only head coaching change.

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Dubas turned to a familiar face in Sheldon Keefe, with whom he’d worked in OHL Sault Ste. Marie as well as the AHL Marlies. Dubas’ patient approach when it comes to coaching told a very different story from the one written in the decade prior to his GM tenure — a period in which the club saw five different head coaches.

From Muzzin to O’Reilly: Going all-in at the deadline (and raising the stakes every spring)

Dubas did some of his best work when the stakes were highest, making trade deadline season a fun time to be a Leafs fan over the course of his tenure. While Dubas often stated his desire to keep his first-round picks, he also wasn’t afraid to deal them away in favour of stocking up at the deadline while making clear his desire to keep his top prospects in-house.

In 2019, his first deadline at the helm, he acquired defenceman Jake Muzzin — a slam-dunk trade that checked all the Maple Leafs’ boxes (defence! grit! experience! term!) from the Kings. One year later, he went back to L.A. and landed Campbell and forward Kyle Clifford.

As playoff expectations heightened, Dubas’ deadline swings got bigger, and more rental-focused. He landed Nick Foligno from Columbus in exchange for a first-round pick in 2021, and one year later focused again on acquiring leadership when he traded for Mark Giordano out of Seattle.

And the grand slam came this past spring when he pulled off a three-team blockbuster to bring Ryan O’Reilly and Noel Acciari to Toronto. He also traded for Jake McCabe and Sam Lafferty, sent Rasmus Sandin to Washington, and brought Luke Schenn in from Vancouver. The series of trades made Toronto the busiest deadline buyer in the league and made clear Dubas’ all-in attitude and willingness to continue betting on his core — from his first days at GM to the final.

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