Either he has some kind of information, has prepared enough of a golden parachute that it won't negatively effect him personally, he's naive, he's short-sighted enough that he really doesn't think of shit to come or he's already got a strategy in place to start a new company up at the drop of a hat.
Yep. Even if he was concerned he wouldn't want to express that publicly, because his teams would all start jumping ship. Then he'd have an actual delivery problem on his hands and the chance of closure would be much higher.
That said, any studio owned by Microsoft should be worried. They demonstrated that even producing popular, highly-acclaimed games isn't enough for them, so there doesn't seem to be a way to keep them happy.
Plus to admit that would be to express doubt in the parent corp, and that sounds like a good way to get on their bad side and have them start having doubts about you.
Oh absolutely, but if you're part of MS then going around saying you're worried about MS is a good way to create a self fulfilling prophecy where you definitely need to worry about it, where before you might have actually been fine.
True though I like to think he's prepared, just because I like Obsidian and hope they can pull off a BI -> Ob again... even if it means my dreams of an Obsidian-made Fallout go out the window.