The Cubs have more than enough. Teams with far less revenue are signing multiple deals larger than any single contract the Cubs have on their payroll.
The problem isnt the money, when it comes to the Cubs. The problem is we have a FO that seemingly operates with the belief that every contract needs to have surplus value. Outside of Max Scherzer's deal with the Nationals, I dont think there's a single mega deal that ended up in favor of the team. That doesn't stop the financial muscle of the sport from paying the price, but it sure does chase away Jed Hoyer.