Yes, a successful businessman with a lovely wife, great family, millions of dollars, and strong legacy is a failure.
He's held high political office before. It did not go especially well, except for something that he's now running away from.
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Obama's position is favored right now to the extent that his best bet will, I think, be to try to simply run out the clock. Both sides running plodding, negative campaigns, all else being equal over the next couple of months, will I think lead to results vaguely similar to 2004, possibly a bit less narrow for the incumbent.