Smoltz, Penny, Escobar, Sheets, add them up and you might have a starter good enough to actually be with the team in September. I hope Theo learned his lesson and is not relying on contributions from these guys. In addition to an impact starter? Fine.
What lesson is there to be learned? That they should have over-extended for a Burnett or a Lowe and potentially blocked Buchholz all together?
Last year, they had Beckett, Lester, Matsuzaka, and Wakefield slotted in the rotation heading into the off-season, with Buchholz, Masterson, and Bowden waiting in the wings as possible 5th starters. So they signed Penny and Smoltz with the idea of the two of them plus Buchholz/Bowden/Masterson combining to put together a reasonable facsimile of a 5th starter and provide adequate fill-in for the inevitable DL trip by Wakefield. Buchholz did emerge per the plan. Penny had a decent stretch as well as a pretty ugly one. From that perspective, they accomplished exactly what they expected with those moves.
The unforeseen part was really Matsuzaka missing four months of the season, which raised the level of needed production from a composite 5th/6th starter to at least one of them being a solid 3rd/4th starter. They didn't intend to rely on Penny or Smoltz (or Buchholz or Bowden for that matter) to give them that...but Matsuzaka's injury in particular forced it.
Right now, they already have Lester, Beckett, Matsuzaka, Buchholz and Wakefield slotted into the rotation for 2010. So what they're after again is one-year, back-end of the rotation/Wakefield insurance type guys with upside, not necessarily a multi-year, multi-million dollar free agent overpay that gives them no flexibility at all moving forward. I think the only way they go the big name, big dollar route for a starting pitcher is if they deal Buchholz. Otherwise, I think they're seeking short-term solutions again this winter, and that means taking on a Harden or a Sheets or a Duchscherer or an Escobar.