Presumably we'd get at the very least a strong indication of signability before making the deal. I don't think that will happen with the Yankees, Mets, Red Sox, Dodgers, Angels, and Rangers willing to outbid each other. We're one of the big spending teams too. But we're not as desperate as some of those underachieving teams with deep pockets. How do you figure? At what point do you become desperate, when other teams make trades and become better than you? You play every year to win the WS, not to hold of and hope next year is better? I would understand your point if this was Tampa Bay and someone is asking for 2/9 of the everyday lineup for CC, that simply is not the case. If the Cubs lose in the playoffs without making any moves are you going to feel comfortable not knowing what could have been. Pie and Hill are not anywhere near an Elite Prospect that you simply hold on too. There is no guarantee of winning a WS next year keeping them. You don't know if Lee, Aram, Carlos, Soto or anyone will be healthy. If they get off to a bad start you don't know if you can make up the ground. There are ifs in every single scenario possible. I would much rather go all out on the year that the team is actually playing great, then wait around for another year that simply may not be matched. Remember 2004. 2004 we did "go for it." The problem with your argument is this: people repeat ad nauseum. Pretty much every year every body wants a "go for it" trade for a guy who isn't really a difference maker and that wipes out the farm system. Hell, we saw it this year with Brian Roberts. Trade everybody for Brian Roberts because it's been a long time since we won the World Series. Brian Roberts is the missing key. Brian Roberts is a 1000 VORP improvement over DeRosa. Brian Roberts is the legitimate leadoff man who will lead us to the promised land. We haven't won a World Series in 100 years so he's worth overpaying tenfold for. I've seen your argument too much to be moved by it. Myself, I think the biggest PLAYOFF difference maker would be a healthy Rich Harden. It's hard to get worked up about any pitcher with a pulse as the 100 year difference maker.