You know, it's actually kind of surprising Maddon hasn't decided to bag this whole situation, considering he'd have no issues finding another job and how highly he thinks of himself. Basically the offseason has been:
Theo says your team lacks urgency.
Theo says the team is "broken", then says a few weeks later he's basically going to roll with it.
The F.O. blows up the coaching purge you instigated and fires the guys you wanted brought in.
The F.O. not only refuses an extension, but says you'll be "evaluated" during the season.
For someone with Joe's pedigree this seems like a really untenable situation, a big blow to his pride at the very least. If things don't start off well next season there's potential for them to go off the rails quickly and disastrously.