That's kinda the point though. It's not your money, it's the money of the guy who is very careful about how and when he spends it.
Suppose Jerry allows the signings of Alonso, Santander and Kim (the first two of which aren't likely to age all that well). Great. They've forced their way to a 72 win team by Jerry doing something very uncomfortable (for him) with his money.
Do you really feel like he'll then add even more payroll to continue supplementing the roster as the younger talent develops? And then add even more after that to help offset the declines of Alonso and Santander?