This has been explained many times in many other threads. But short version, again: There is no guarantee of winning no matter how much $ a team spends.
Long version/explanation:
That logic suggests that simply dumping millions more into the team won't guarantee a 2nd round win never mind a Cup. So, for example want to replace Shanahan? Great, but he's owed $X million x how many years left on his deal + The cost of a new President, with no real assurance new guy is any more successful. So he stay as at least until his deal runs out.
That is the definition of a team caring more about money than winning.
Example #2: Re-signing Nylander to the best deal he could possibly ever imagine. Willie is a known quantity. With him, the Leafs are likely to make the playoffs every year. Trade him and who knows what effect that will have on the team's success. So re-sign him and enjoy your 1-round of playoffs every year.
That's a risk-adverse team that isn't seriously committed to winning (it all).
So, yes, MLSE wants to win. Everybody wants to win. But they are not committed to the goal of winning it all regardless of the costs, rather they are committed to winning with conditions. (Or as I'd offer, limitations. Do with this core, under this President, etc.)