The truth of the matter is the Pirates' organization has to be run differently from the Cubs' organization. They can't afford to keep players long-term with the hopes of adding on later. They have to know they'll have a minimum of inexpensive contributions at the major league level before they can even consider being in "buyer" territory. At the end of the last regime in Pittsburgh, both the major league squad and the minor league system were abysmal. Prior to that point, trades weren't made to improve the system, they were made primarily to dump salary. Here's the way I see the three trades mentioned, from Pittsburgh's perspective: - Aramis Ramirez - People easily forget how bad Aramis was for the Pirates in 2002. In fact, there was an article out there somewhere indicating that Ramirez's 2002 was the worst statistical year ever for a cleanup hitter. Yes, he was playing hurt, but management wasn't willing to let that go, with what they were paying him. As a result, Aramis was very disinterested in playing for Pittsburgh and gave little effort. That, combined with the injury and the cost, was more than enough to convince Pittsburgh to dump him for what at the time were considered to be decent to good Cubs prospects (Hill, Bruback) and a stopgap 3B (Hernandez). - Jason Bay - Bay was a year away from free agency, and the Pirates were more than a year away from contention. Rather than get nothing for him, they got what many considered to be a good package of prospects from the Red Sox. - Nyjer Morgan - Really, the Nyjer Morgan trade was likely a case of selling high on a productive OF to improve the system. The real question here is why Washington did the deal.