Halladay is clearly the better pitcher, but we don't need to do this. We have plenty of prospects, that's not the problem. We may have the prospects, but we also need them. This team will need an influx of young talent to makeup for the inevitable decline and departure of the core of this team, which is already too old. If you can keep your overall prospect balance constant, or near constant, while upgrading your veteran pitching situation, that would be pretty nice. So are the Cubs "already too old", or do they need to "upgrade (their) veteran pitching situation" by swapping a 28YO for a 32YO? You'll get no argument from me that Halladay > Zambrano, but if you're truly concerned about the age of the team, then this is a big step in the wrong direction. It's increasing the age at one spot, but maintaining the prospects. Zambrano isn't young. He's got a lot of miles on his arm and has shown signs of serious wear and tear. Halladay has been a much more stable and effective pitcher. That's not a big step in the wrong direction at all. Halladay is better now and likely to be better for a few years. You upgrade the team, but at the same time you don't trade away prospects, or at least you don't take a significant net hit in prospects. I see no way this actually happens, but it would be a good thing for the Cubs if it could. The advantage of having prospects around to replace the older core is they are cheaper to employ, have room for upside, and presumably have a much larger window of time where they can be useful. Zambrano is already ridiculously expensive, he's shown a likelihood of already having passed his prime and settling into a lesser pitcher, and he may or may not have a lot of years ahead of him. Swapping him for Halladay doesn't really have any negative repercussions on the age of the core.