You have to be willing to do it at the deadline.
If the Rockies (somehow) or the Phillies are 3/4 games out of the last wild card spot at the deadline, and there are guys in their system that you really think are well underrated, you need to be able to take advantage of that.
In the off-season, teams will dream on their prospects stepping up or reclamation projects. At the deadline, a team under ownership pressure can mess up.