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The Lieberman move troubles me much more than the former Clinton staffer picks.
The Clinton staffers selected so far are all experienced hands who should do well in their jobs. Even the Hillary Clinton pick is one that I can see an upside too. The length of the vetting I don't see as unusual given that Bill has a lot of baggage post-presidency. It sounds like they've only started work on this stuff. Also, airing some of these things out in places like the NY Times has the potential to deflate some of the criticisms later. The idea is to get ahead of the problems and to frame potential concerns in a way that serves the interests of a Clinton nomination (e.g. it's a way of saying "we've looked into these things and everything turned out OK" -- or perhaps they may say "things didn't quite work out"). I do think that Hillary can keep some distance from Bill and mitigate some of these questions. It's a choice that has some risk and some upside.
The Lieberman move essentially puts him in a good position to advance the interests of Lieberman. As was the case over the past two years, Lieberman will turn a blind eye to companies who have business before his committee; the companies will in turn reward Lieberman with robust campaign contributions, and his cash position will be in a good place going into the 2012 re-election contest. Meanwhile, it's hard to see how the public interest is served by having a doormat as the chair of the Homeland Security Committee. More likely, when Lieberman uses his chair it will be to embarrass Obama. If that happens, Obama has no one but himself to blame. He made a gamble that could very well blow up in his face. In terms of the upside, well, it helps him win a couple news cycles, and perhaps a vote or two from Lieberman on a marginal issue down the line. I would have called Lieberman's bluff and given him a minor committee post -- and run the risk of bolting the caucus in the interim and running as a Republican in 2012.
The signal that this one sends is that Obama is desperate to co-opt those who disagree with him; even if it loses him core support. Hopefully he proves me wrong.