People with the drive to do what Theo has done generally don't get into a "there's nothing more for me to accomplish why don't I just keep doing what I'm doing" state of mind. He also explicitly stated in his first press conference that after 10 years a change is good, hence the reason there's a huge correlation between the core's FA timeline and his second 5 year contract. Assuming Theo leaves at that point, best case scenario would be Jed moving into his role and perhaps McLeod as GM (if he hasn't already taken a GM role elsewhere). Ok, but people change and their priorities change. For those of you that have kids, consider how much that has changed your priorities. That being said, I completely discounted the idea that an ungrateful fan base might demand he be fired if the Cubs don't win another title in the next 5 years.