Epstein's best deal is the Bay deal. They managed to unload Manny along with $8 mil and got Bay in return without losing any of that young unproven pitching Theo holds close to his heart. Said in jest. After all, others are involved in these decisions, as well. Anyway, the Bay deal was a great one. They were in a real pickle at the deadline with Ramirez.
His other deals have fizzled. Gagne cost them 4 straight games against the Yankees in September with four blown saves in a row. Fortunately they were 6 games ahead of NY. Pineiro is pitching pretty well in St Louis where Duncan is the pitching coach--one of the best.
The best deal the Sox have made lately is the one for Lowell and Beckett, which Theo did not make. They won the 07 Series with that deal. They gave up an MVP SS in Hanley R., but he wouldn't have gotten them that 07 Championship. And wasn't he in AA at the time? He got his chance because he went to the Marlins. In Boston, he spends another year in AAA.
Some say they would not have made the Beckett deal if Epstein had been calling the shots. If they hadn't won in 07 without Beckett, he might be viewed in a different perspective now. I suspect if he doesn't get Halladay or VMart by tommorrow, he might be on the hotseat in the media.
Oh yes, forgot about the Cabrera deal. Great deal, too. Cabrera was an obvious fit. But then they didn't re-sign him after winning with him. Big mistake.