I think the next Xbox is going to be the thing that finally takes him out. Not one gamer I know wants one, and the 360 works just fine for the family. They managed to derail what was one success story he could actually point to... It's going to be an epic bellyflop. I say he's out after the sales figures come in next year.
The XBox was really the only diversification from their core Windows/Office business which has really even slightly worked, though. MSN/Windows Live/Bing/Whatever it's called now was a massive cash sink and market failure, as was Zune and Windows Phone. Azure is looking like it's heading that way too, though no-one's making much profit in that market right now.