It all started with Nylander's much maligned contract. The 6-year deal pays Nylander $7.5M per season, but due to his holdout, costs the Leafs only $6.9M against the salary cap. Next Auston Matthews signed a 5-year deal paying $11.634M per season, nobody really complained about that one because Matthews is just so incredibly good at hockey. The Marner contract, like Nylander's, was raked across the coals, 6 years at $10.893M per season. Dubas certainly wasn't shy about paying his top end talent even before they'd realized their full potential.
The thought process is solid enough. Pay players for what the will be, not what they were. Doing so has worked out quite well for the Leafs as they've avoided signing those albatross contracts we see every July 1st. By avoiding contracts that pay players high salaries through their decline, the Leafs have retained cap flexibility even while being tight to the limit because all but one or two of their contracts are easily moveable.
Now, we are seeing more and more of this happen in the NHL, the Tim Stützle deal being the latest example. 8 years at $8.35M is a massive amount for a player that hasn't hit 30 goals or 60 points yet. The Sens are betting on 2 things; Stützle's continued development and a massive rise in the NHL's salary cap. Cale Makar's $9Mx6 deal follows the same logic, as does Mikko Rantanen's $9.25Mx6 deal - though the pair of Avs were already much closer to their peak than the younger Stutzle.
Of course, the Leafs didn't benefit from the rising cap the way they should have. The timing of the COVID-19 pandemic was about as bad as it could have been as far as their cap situation goes. Still, it appears Dubas' philosophy of signing players to big money deals right out of their Entry Level Contracts is catching on. This begs the question, is Kyle Dubas really a bad negotiator, or was he simply ahead of his time?