Dubas is managing this team as if this was a Fantasy Hockey who scores more points stays. You need Bozak and JVR and Komarov, and Hyman and Kadri to win. You don't need Nylander and Tavares cause you already have Marner and Matthews. Look at CHI 3 cups, well balanced team, thru out including D (Keith, Seabrook, Campbell, Oduya, Hjamarson). Look at PIT, they are super top heavy and yet, top 4 players make $30M, while TOR now top 4 will make $40M. Thats not going to work. You can't win cups this way, who you go on D? Berri? why? you need shutdown people not point getters, you already have F core that can score a ton... I don't get it... I guess management wats sell tickets, and jerseys and could careless about cups.
Toronto is going a little heavier on skill than a lot of teams in the past have, but there is a strong indication that skill wins, not this idea of gritty pros. Pittsburgh won a cup, but then when they traded away Staal because they thought it was too difficult to win if you were top heavy, they spread their cap around and didn't win again until they added another high skilled player who doesn't play D, and doesn't hit. After those cup wins they seem to be sliding as they traded away smaller skilled guys to get grittier, and have made room for Johnson and Tanev at the expense of Kessel and Sheary.
Chicago was a pure skill team. It's great they were lucky enough to have some grittier skilled players, but they stayed competitive by keeping a core of Toews, Kane, Hossa and Sharp together and made room by moving out high end secondary guys. It's when the core started aging itself out that they started sliding, and became reliant on just a couple of superstars rather than a strong group overall.
You chose Bozak and JVR as the types the Leafs need? Why is JVR more important than Nylander? He's older, neither is physical, he's worse defensively, and costs the same against the cap, so is being less skilled going to help? Bozak is an expensive third line center, but again, they had him and didn't win, keeping him so you can't afford Tavares doesn't make your team better. He was part of a cup winner who used him to supplement things, but they won using the one real strategy shown to be effective. They had a competitive team for a long stretch of time, they kept making hard choices on non-core pieces to make sure they didn't completely wreck their cap (this is a team that let "heart and Soul Captain" Backes walk), and they kept extending their window until they caught the right breaks.
Look at past winners and teams that are successful, Washington, Pittsburgh, Chicago, St. Louis, Boston, LA. They all had lengthy windows built around solid cores. A team like LA started to fall off when they started giving out big money to legacy guys, and buying into the idea you needed certain types of players to win, rather than adjusting around their core and making some tough decisions as guys were at an age where you know a contract will be an anchor.
If anything Chicago was it's best when needing to basically reshape their D and bottom part of their forward group every year to fit under the cap, it's only when they started deciding near 30 year old bruisers like Seabrook, and guys like Bickell deserved big money that they started tying up their cap money to less than stellar contracts that basically tanked their success. Now they have started leaning harder on skill again (Debrincat, Gustaffson, strome) and their top tier guys are still effective and they look a little more competitive again, but that Seabrook contract, and the Saad trade were a team that declined because they started favouring Grit over skill.