They lost money one year therefore all the following years they had to make up for it.
I don't know if it was accurate, but I read that they netted @$56 Million after expenses last year. That's $200K/kid/week. And that's only the Cubs revenue.
He's in a tough spot, I think most GMs are like Jed and don't mind higher AAV on shorter deals and Cody wants a long-term contract. I think that ship has sailed over the horizon.
This team is a disaster. It's not a tweak here or there from a good team (I DGAF about being in the playoff mix). I don't know how Jed can run this group back out there next year with the same core and expect them to score any runs consistently.