The crapshoot thing isn't being overstated. It's still being understated. The very fact that people are making arguments for trading Kyle Schwarber for relief help in the playoffs is practically objective proof of this. The best way to maximize winning ONE World Series (nobody is saying anything about multiples) is to maximize your chances at making the playoffs numerous times. Having Kyle Schwarber for 5 years beyond this one does more to that end than Andrew Miller for a little under 2.5 (and, for that matter, Chapman for a little under half). Except they are already virtually in this year and have an ageing pitching staff. I think those two would make the pitching pretty dominant as it shortens the outings for everyone. At this point, who do you have confidence going deep into games? Lester? What is the marginal value? Are you considering leverage? Simply comparing projected WAR is over-simplification. Where is Schwarber going to play? Who is not going to play then? I understand your point and maybe you are right, but I think it's simplified too much. Having a better team in October does give you a better chance to win. The bold is precisely why it's even sillier to trade future assets off for the short term.