It is clear that Obama and his team are focused most intensely on the present, namely a clean ending in Iraq, no screw-ups with the drawdown in Afghanistan, and starting at the top rather than the bottom of the learning curve regarding other problems that could flare up in the Middle East. If those are the priorities where the administration wants to take the smallest risks, Dempsey is a strong choice for chairman.
Dempsey's personal experience with counterinsurgency in Iraq directly transfers to both the final endgame there and to advising the President on the fight in Afghanistan. Of even greater importance is Dempsey's experience with security force assistance both in Iraq and Saudi Arabia. The biggest problem the United States has in Afghanistan is not with suppressing the Taliban; the Taliban, or something like them, will always be there and will always be fighting somebody. The biggest problem lies with standing up useful Afghan security forces. In Dempsey, Obama and Leon Panetta will have someone who can give them experienced advice on this issue. Perhaps equally important will be Dempsey's personal knowledge of Saudi Arabia's security forces, both regarding Saudi internal security and Saudi Arabia's ability to fend off a challenge from Iran.
One storyline out of the Obama administration is its professed eagerness to extract itself from the Middle East and Central Asia in order to focus on East Asia and the Pacific. If that was the most urgent priority and the place where Obama wanted to minimize risk, perhaps Adm. James Stavridis would be the next chairman (think you can't have admirals as back-to-back chairmen? President Clinton had soldiers for chairmen, back-to-back-to-back.).
Of course, just because a soldier will be chairman does not mean that the development of the Air-Sea Battle Concept will stop for the next two or four years. Dempsey is very smart (something I have observed first-hand), has experience in joint billets, and has his picture next to the word "adaptable" in the dictionary. As a hedge, Obama has selected Adm. James Winnefeld, a former carrier strike group commander, as the next vice chairman. As vice chairman, Winnefeld will chair the Joint Requirements Oversight Council and co-chair the Defense Acquisition Board, two critical posts regarding the capabilities needed for the Air-Sea Battle Concept.
With his national security appointments over the past two months, Obama revealed some surprises. But the logic is clear: minimize risks to operations in the Middle East and Central Asia by appointing those with the most experience in those areas. East Asia, the Pacific, and Adm. Stavridis will apparently have to wait before they get the same level of attention.