Edited Sep. 20, 2023 at 10:18 p.m.
Quoting: TheresAlwaysNextYear
You also have to take into account signing bonuses and endorsements, both of which he'll get more of in Toronto than Tampa
There's a big difference between the potential money he can make in Toronto and what he's actually getting offered. Matthews and Marner are getting the bulk of endorsements $ in Toronto, yes, Tavares, Nylander, and other players make money off endorsements but that doesn't mean that it's going to be so much that he can't make the same money elsewhere.
As for bonuses, there's no guarantee that Toronto will pay Nylander most of his contract in bonuses, and if they do then that just helps to bridge the tax difference, if they were to concede to his demands of 10M+. The Leafs are supposedly offering something in the 8s though. In TB, Nylander's contract is probably going to be either structured like Kucherov, Point and Vasilevskiy who get 58% of their salary in bonuses, or like Sergachev, Cirelli, and Hagel who are getting 33/34% of their salary in bonuses. 9.1Mx8 in TB at 58% signing bonuses nets more than 9.1Mx8 in Toronto with 91.8% of salary in bonuses. It's kind of nonsensical to include endorsements since that's not the team that is paying them, he can get endorsements elsewhere and Nylander isn't going to lose the deals that he already has signed (if I'm not mistaken, he inked a big deal this off-season).
My whole point though, is that Nylander just wants to be respected, so if TB is offering him 34% in bonuses, then I don't think he signs at 9.1M, but if he's getting the same pay structure as the superstars in TB, I wouldn't be surprised if he takes 3.2M haircut on the overall contract. Although he might be adamant about getting that exact contract, at the end of the day though, the max they can give him based on this roster is 9.385M per year which is probably good enough.