Former Maple Leafs GM Reveals Biggest Regret

Kyle Dubas' time with the Toronto Maple Leafs was far from perfect.

Jon Alfano | Jul 12, 2024

Jun 22, 2018; Dallas, TX, USA; Toronto Maple Leafs general manager Kyle Dubas announces the number twenty-nine overall pick in the first round of the 2018 NHL Draft at American Airlines Center. Mandatory Credit: Jerome Miron-USA TODAY Sports / Jerome Miron-USA TODAY Sports

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Toronto Maple Leafs

Kyle Dubas' time as the general manager of the Toronto Maple Leafs was full of ups and downs, and now that a year has passed since his departure, he's had some time to reflect on the journey.

While Toronto was one of the best regular-season teams in the league, playoff success was near non-existent with numerous first-round exits.

The Maple Leafs finally broke through in 2023 to defeat the Tampa Bay Lightning in six games, their first series victory in 19 years, but were quickly dispatched by the Florida Panthers in the second round. At that point, it was too little, too late.

In retrospect, there was one moment that defined Dubas' tenure in Toronto more than any other: signing John Tavares to a seven-year, $77 million ($11 million AAV) contract in 2018. Six years later, Dubas reflected on that moment in the upcoming book "The Franchise: The Business of Building Winning Teams," written by Craig Custance of The Athletic. Dubas said he doesn't regret signing Tavares to that deal, but he wished he handled some aspects of it differently.

“The biggest mistake I think I’ve made in my whole time here has been not taking care of the three incumbent contracts,” Dubas told Custance, per the Toronto Sun. “(William) Nylander was up, (Mitch) Marner and (Auston) Matthews could have been done on July 1 extensions.

“The thing I learned was once we signed John to the (AAV) we did, it lifted the lid on the entire ceiling."

Really, the problem wasn't signing Tavares to that deal, but the can of worms it opened. Nylander signed a six-year deal worth $45.09 million ($7.51 million AAV) in December of 2018 after a holdout, Matthews signed a five-year deal worth $58.2 million ($11.64 million AAV) in February of 2019, and Marner signed a six-year deal worth $65.41 million ($10.9 million AAV) in September of 2019.

The problem with those deals isn't necessarily the value of them, but that they got unrestricted free agent money when they were only restricted free agents. Toronto dedicating over $41 million, roughly half of the salary cap, to four forwards proved to be a mistake, as the team has constantly struggled to put a good supporting cast around its superstars.

Granted, the Maple Leafs were arguably the team most-affected by the league's stagnant salary cap as a result of the pandemic. Without the cap going up as expected, an already difficult situation became so much harder to deal with.

“What would the cap be, $90 million?,” former Maple Leafs consultant Darryl Belfry told Custance. “Kyle would never say it, but I will. You have a world shut down, it’s a flat cap for multiple years and you’re stuck holding the bag on a projection. You didn’t miscalculate, it’s an act of nature that beat you.”

"The Franchise" releases on Oct. 15, and Dubas isn't the only NHL figure featured. The book also includes interviews with Lightning coach Jon Cooper, New York Islanders general manager Lou Lamoriello, Dallas Stars general manager Jim Nill and Washington Capitals owner Ted Leonsis.

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Published Jul 12, 2024

JON ALFANO