I have stated before that I almost wish that the Sox were a small market team. I fully appreciate Henry's willingness to spend, but I don't think that we have to forego small market philosophies just because we have a big budget.
It will take us a few years to get the farm back to where we want it. In the meantime, high quality, stop gap players can be found to keep us in contention. It will take quite a bit of work, but it's possible.
I don't follow player development very closely, but I have often wondered about our player development system, or lack thereof. Even though we are not typically drafting high, you would think that somewhere over the recent years, we would have developed a solid starting pitcher.