Signing Tavares before Matthews and company: Kyle Dubas’ biggest mistake, according to him

In recent years, whether you like the Leafs or not, you have to admit that Toronto has been one of the most dominant teams in the regular season. Unfortunately, as we all know, the Leafs are incapable of winning in the playoffs.

Since 2004, they’ve only won one series. That was in 2023 against the Tampa Bay Lightning.

There are a number of factors behind this failure, and one of them is certainly the general managers’ inability to balance the roster.

Offensively, the club is stacked. Defensively, it’s a little more difficult, and in front of the net, the situation has never changed; Toronto has always been in search of a true number one goalkeeper.

It certainly didn’t help that so much money was invested in four forwards. And the why of it all: the timing of the signing of captain John Tavares.

Kyle Dubas talks about his biggest mistake as Leafs GM in Craig Custance’s new book, that was not signing incumbent free agents Matthews, Marner and Nylander before signing UFA John Tavares, once they signed Tavares to that AAV it lifted the ceiling for the other 3 core players.

– NHL Watcher (@NHL_Watcher) July 20, 2024

Indeed, writer Craig Custance spoke with Kyle Dubas, among others, and in his latest book, he reveals that the former Toronto GM’s biggest mistake was signing Tavares before Auston Matthews, Mitch Marner and William Nylander.

It was Tavares himself who admitted his biggest mistake at the helm.

In 2024-2025, the captain’s seven-year, $11-million-per-year contract proves to be a millstone around his neck. Good thing the pact expires in July 2025… Not only is $11 million a lot for a guy who’s slowing down, but it also set the standard for the other three star forwards in the lineup, who are better than Johnny T.

Dubas went to great lengths to negotiate, in any case.

The result is that Matthews has signed two contracts (one for $11.64 million and another for $13.25 million per year) since Tavares arrived. Nylander signed for $11.5 million and Marner signed for $10.9 million a year after the captain. Nearly $47 million annually for four forwards isn’t exactly ideal.