The news that Theo Epstein could be on the move to the Cubs came back before the September collapse was in full force, and at the time it seemed like a ridiculous notion. The GM was under contract for another year, in a good position with the Sox, and quite possibly on his way to leaving another positive mark on his record with the team.
Then the Sox went 7-20 in September, missed the postseason in the worst possible way, and everything changed. Terry Francona left citing various frustrations, and the Epstein-to-Chicago rumors resurfaced with a vengeance. Now, less than two weeks later, it appears that the Sox' GM of nine years is indeed on the way out.
With one year left on his contract, the Red Sox did have the ability to avoid this, but with the Cubs move likely a promotion,baseball etiquette dictates that they remain open to the deal. They do not, however, have to let him go for free, and will almost certainly see some level of compensation for allowing him to leave. Exactly how much that will be worth is yet to be seen, but suggestions that a top prospect could be on the way in or an albatross on the way out seem optimistic to say the least.
If Epstein is indeed gone, smart money is on assistant GM Ben Cherington taking over. While it would be encouraging to have someone who has been in position to see how Epstein works (and draw hopefully the best aspects from it), the fact remains that he will enter unproven into a situation which requires a great deal of work to be done. "Trial by fire" doesn't exactly cover it.
This hasn't happened yet, and it's hard to see the Sox letting him go without a fight, but I'd be surprised if Theo is around come the end of the week.
Be on the lookout for Gorilla suits around Fenway Park.