I think the impact of Chapman to the Cubs has been underrated here. Theo gave up a nice prospect for a damn reason. He knows that the Chapman add transformed the team's weakest phase -- bullpen -- from below average to one of the best. They crunched the numbers and figure that Chapman moves the Cubs from 20th bullpen to the 4th. They also added LH Montgomery and Joe Nathan is back in business and looking good. Now you got Rondon as probably the best setup man in the 8th and also Strop. Bullpen was a weakness for the Cubs, but no longer. And I'd argue that one, or two, dominant closers are even more impactful in the playoffs with all the days off. How many playoff games did Familia pitch last year? Almost every one. Chapman can easily do the same, plus multiple innings. Guy is a freak and looks stronger than ever.
Cubs hitting and starting pitching already among the top few in the league. Add bullpen and now Cubs strong in each phase. Crunch the numbers and find that the major bullpen upgrade could have moved the Cubs from 25% to 35%. Those are significant odds. You can damn well bet that Theo crunched the numbers and knows to a degree of confidence how much Chapman moved the needle in terms of odds of winning this season and you can bet it was significant. When it comes to best executives, there's Theo and then there's everybody else. There are NO guarantees, but you keep putting down good wagers and you like your chances. Theo loses very few bets. This is a different type of risk, but the timing and rationale was right to make such a wager.