It's also one of the biggest decisions of his life. He may want to ruminate on it a bit.
I don't think he will drag it out unnecessarily. He and his team probably don't want to be seen as holding up the whole offseason either.
I think he will decide before Christmas. We're down to the last few days of torture.
If I'm comparing the Sox to other teams right now the big negative is the *apparent* dysfunction in the front office. I think the Sox have a bad rep in this area right now, and all the people who declined to interview for CBO are more evidence of it.
There are no guarantees that any franchise will be successful for the next decade.
But having an owner with a ton of money who wants badly to win surely helps the profile a bit.