2022-24: Breaking Through
At this point, the core has grown into their primes and have shown who they are as players year after year.
In 2022, they suffered their fourth Game 7 loss, but this time to the Tampa Bay Lightning. They would rematch with the Lightning in the first round the following year, and after six seasons together, the group made it out of the first round, ending a 19-year franchise drought without a series win, a series that featured an interaction between Dubas and Lightning fans, which showed a hot-headed Dubas getting into a shouting match with the Lightning crowd at Amalie Arena in Game 3, possibly due to the pressure he was under, as the speculation of him not returning as Leafs GM next season was a good possibility, barring any deep playoff run.
They would ultimately lose in the second round to the Florida Panthers in five games that season, and even after the core's first piece of significant success, Dubas was fired. According to Shanahan, in his press conference addressing the firing, he fired Dubas in what was a dramatic and highly publicized firing. Their relationship was tarnished after a breakdown in trust and a shift in expectations.
Dubas's tenure as Leafs GM will be remembered for making questionable roster and contract decisions due to his lack of experience at the position, so Shanahan went with experience, something he outlined after addressing the Dubas firing. He went with an experienced GM in Brad Treliving.
With Matthews and Nylander due for extensions shortly after Treliving becoming the franchise's 18th general manager, it's at this point many were hoping for the experienced Treliving to put an end to the egotist contract negotiations between Toronto's biggest stars.
Unfortunately, the continuing trend of Toronto's biggest stars breaking the bank continued, as Treliving extended Matthews to a $13.25-million AAV deal, making him the highest-paid player in the league, and then extended Nylander a few months later to an $11.5-million AAV contract, both signed lucrative deals with still only one series win in the playoffs, but due to the benchmark signings done by Dubas back in 2018, the two players were once again comparing each other's worth for their own benefit, scratching for every nickel and dime they could from Leaf's management, further tying management's hands in building a competitive supporting cast around the core.
It's at this point that the Leafs were clearly locking up Matthews and Nylander for the foreseeable future, deals that will take them through their primes while letting Marner and Tavares play out the final years of their contracts.