We have no idea what is a Ricketts directive or not, or what Jed believes in or not. All of these discussions are done behind close doors. The only thing we really know is that Tom very likely sets the maximum payroll since its his money and not Jed's. If Jed could have a 280m payroll every year he would. We have no idea about Jed's true feelings on big star contracts, for example.
If Jed disagrees with something Tom wants it doesn't matter, Tom is the boss. Is Jed going to quit because of it? I wouldn't, there's only 30 of his job in the world. Jed and most other people are going to publicly go along with it, he certainly isn't going to air his disagreements with his boss in public.
I think Tom likely sets certain parameters (e.g. max payroll) and Jed does everything he can to win within those parameters. We don't know what those parameters are.
Jed going into 2025 with an expiring contract isn't good though, I think it would mean that Ricketts is at least not 100% happy with Jed's work within those parameters the last few years, which is understandable given the results.