do not agree with the OP's position. Taxes don't have as big of a role to play.
- Leafs do rcas, which NBA has banned
- Leafs players makes more revenue in advertising and marketing than any other players in the league unless you are Ovi, Crosby, McDavid
- Leafs can front load the contract like few other teams can
why front loading the contract matters?
- You get a lot of your money a lot before
- You can invest in a property NOW instead of waiting, and then earn higher rate of return. Imagine Marner buying property before pandemic, and then the ridiculous house price increases during the pandemic itself especially in Toronto, and marner selling these properties at the inflated prices. This higher rate of return is only possible when you have a large capital available "Right Now"
- You can also invest in stocks/currencies/funds etc... "Right Now" instead of waiting
- Simple Example: investing 1 million in a fund that has 1% rate of return versus investing 10 million in a fund that has a 1% rate of return.
- Leafs players can make quite a bit of money compared to other players playing for other franchises.
bottom line: I don't buy the tax theory that OP is talking about. For the Leafs thats not a big issue.