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There's very little chance he'll lose realistically. He's sitting in a very comfortable place right now. Just like most economic downturns, there will be an upturn and it will most likely happen right when the current administration is up for re-election. The president will say that it is due to his policies including health care/insurance reform as well as the economic stimulus. He may be correct, he may not, but the public will not be able to refute his claims, nor will they care much to.

Bottomline, if the country as a whole is in better shape then prior to when Obama was elected, he'll almost certainly be re-elected. As things currently stand, things are looking good for him.