7. Kevin Turner: The current COO for the last eight years, Turner spent the previous 20 years at Wal-Mart Stores (WMT). He certainly knows the company from his time there, but I suspect he'll be seen as "Ballmer's right-hand man" and not a Microsoft "lifer" by this board. When the new CEO arrives, Turner will probably be first out the door -- just as we saw with David Ko at Zynga after Don Mattrick arrived.
8. Tony Bates: If Microsoft wants to give the impression that it's making a big break from the past while secretly ensuring that it's still getting an insider, then Tony Bates might be the man. The former head of Skype now has been integrated into the borg for a couple of years and was just promoted. Still, I think Gates would feel more comfortable with a longer-tenured enterprise person.
9. Eric Rudder: This would be my "dark horse" insider pick. He's currently head of Advanced Strategy and Research. Research has mostly been a sinkhole for Microsoft in the last 15 years, and Wall Street knows that, so it might be difficult for the board to sell his selection as top executive. However, Rudder used to be SVP for Server and Tools and also worked closely with Bill Gates on Technical Strategy before that. That might put him in favor with Gates, who ultimately will make the call.
So, from where I sit, the most likely -- which is not the same thing as saying the "best" -- outsider is Elop. The most likely insider is Nadella.Of the two, I see Nadella as the one the board would feel most comfortable with. At the time of publication, Jackson had bullish positions in ZNGA, AAPL and YHOO. Follow @ericjackson This article is commentary by an independent contributor, separate from TheStreet's regular news coverage.