If that's the case then then I'm going to start wondering if Theo is doing what he feels is best for the organization or if he just wants to do a video game rebuild and is going to whether it's the smart thing to do or not. At least with Pujols you had the concerns over being an albatross later on because he's old, but with Headley there's no valid excuse other than we don't want to try to win for a long time. He's really good, he's right in the middle of his prime, he's relatively cheap (for his production), we have a gaping hole at third, and he has multiple years of team control even after this year. He plays really good defense, has a very good approach - he's Theo's type of player in a nutshell. If they ask for something we can't give, I fully understand that (or something system-crippling). But to pass on him because we don't plan to compete until he's a FA is a self-fulfilling prophecy - we won't contend for an extended period of time because we won't add great players when they're available. That's the thing though. If Headley is really good, in the middle of his prime, and relatively cheap....then why do the Padres want to trade him? The likely answer would be the same as the reason the Cubs would trade Garza. It's because they only have 1 major asset to a contending team and would prefer it if they could get 2 or 3 good players (eventually) for 1 good player. As good as Headley is, the Cubs are in the same boat as the Padres. They need as many long-term solutions as possible. Sure that sucks in the short term, but it also doesn't make much sense to trade them 2-3 long-term solutions for 1 solution in Headley. The Cubs are not Headley away from competing. Completely agree with the 2nd point. The next 6 or 7 months will tell the tale about the FO timetable. This is their first trade deadline running a horrific Cubs ballclub. What are acceptable increments of improvement in the next 3 years for the team/organization, for the FO and for the fans? Not that a Headley trade decides this, but this and the near future will tell us a ton. As for the bolded quote I agree to an extent, but the difference is that the Cubs are a big market franchise and that has to be part of the reason this is more attractive a job to Hoyer, more opportunity. The draft is not the only means at their disposal.