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In the sense that he managed to survive being a local and state politician without a criminal complaint or going to prison, I guess.
There are plenty of things to actively like about Obama. He's a smart and well-connected former law prof* whose recent appointments to the White House's Office of Legal Counsel--read Jane Mayer's The Dark Side if you wonder about the importance of it and how a few bad apples in that small office helped wreck America's international reputation--instill me with confidence that he can undo a lot of the damage the Bush administration did. My main hope, which has been confirmed by some (but not all) of his appointments, is that he can return the federal government to at least a Clinton-level degree of competence.
If you think that's a low standard, you should read more about how the Bush administration seeded the Department of Justice, FEMA and the Coalition Provisional Authority in a manner that would make a Chicago alderman blush (clout and ideological insanity). There's a tremendous amount of damage to be undone, probably more than we even realize.
But the idea that Obama's rise to power reflects well on Chicago politics, as keen observers like Steve Rhodes, John Kass, and Ben Joravsky have pointed out with various levels of concern, is patently absurd. He stayed far enough in the realm of probity to not torpedo his chances of being president, which may be an impressive strategic achivement, but holding it up as a sign of local progress does us locals no favors.
* One of the beefs about Obama was his thin political resumé, which may be valid as far as it goes, but his non-political resumé sometimes gets insufficient attention as part of his rise to power. The Bush administration did more damage, arguably, to the federal government's legal culture than it did to anything else. So his connections to politically moderate legal experts, not to mention his own experience, were a selling point to a lot of observers.