I think the thing is the FO convinced him to "spend money to make money" for the last few years of higher payroll on the belief that in this "championship window" they'd have a nice Ferrari which would produce not only high gate receipts but consistent playoff TV money for a few years for JR and his limited partners even if they didn't win a title or even an AL pennant. So he and the limited partners pushed their chips to the middle and opened up their wallets for a few years in terms of total payroll.
Unfortunately, those promised returns never came and between stalled development, injuries etc. the Ferrari they believed they paid for (in reality they shouldnt have expected a Ferrari for a 185-210m payroll but at least it should have been a pretty good car) turned into a 1988 Toyota Tercel with 225k miles on it.
Not content to pay the price of a decent steak dinner for just a peanut butter and jelly sandwich, the FO then compounded the problem by jerking off onto the windshield of the 1988 Toyota Tercel and proceeded to also drive it into Lake Michigan and here we are.
The partnership isn't going to spend again now that they got burned. If we can be mediocre on a cheap payroll or if we are mediocre on a high payroll, the partnership obviously prefers the former and so that's the apparent plan going forward.