Bottom line is the dollar cost average on what the Leafs pay is suboptimal with a very thin margin of error at all levels.
Big guns make glamour money, but across the league in comparison with the Big 4, there’s always someone around the league getting better value. Like NYR gets more out of Panarin than the Leafs with Marner or Tavares. Edmonton gets more out of Draisaitl than Matthews. Colorado gets more out of Mackinnon than Matthews. Pastrnak is always in the Nylander ballpark for salary but he’s competitive with Matthews. Florida and Tampa are literally playing by different rules.
The only place where Toronto has done pretty well is get serviceable mileage out of their cheap goalies. But even that falls apart once the stress test of the playoffs happens.