With the playoff structure, you have to have a special ownership group that wants to top out. The Ricketts of the world want the best they can do at a certain price point.
People have said that the money is there if Jed asks for it. Well, the Ricketts know Jed ain't asking. They have their man. It's a mutually beneficial relationship. They can point to all the times free agent spending hasn't worked and neglect to remember when it has worked.
But anyway, Jed has a MO. He doesn't mind paying larger contracts, he doesn't want a larger contract for a long time. It's not hard to understand the logic, even if you don't always agree with it. It's funny how the times might change, and ownership might change, but they are still the same Cubs who want to be competitive within the division instead of wanting to blow past the division.