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I think you're wrong in suggesting the Clinton team actually "won."
The Clintons, notwithstanding their "new" Democrat label, both had one foot in the Roosevelt/Truman/Humphrey past. That led them to raise taxes in '93 -- a controversial move at the time -- to implement national health care in '94. The Clinton presidency really ended, in a sense, in November of '94. They had no chance to enact the "dream" beyond that point.
Mr. Obama, by contrast, does not seem to have one foot planted in that dream. Of course, he favors big government generally: Robert Gates pushed the DOD over $500 Billion last year; the new Treasury Secretary is as much a borrow and bail fiend as Henry Paulson; and we are now looking at trillion dollar annual deficits, with $200+ billion in interest payments alone, and rising exponentially. But what would the New Dealers think; i.e., the idealistic social planners of the past? Or today, those who pine for Euro-style univeral higher education and health care? I don't see us getting much closer to either of those goals, with this level of short-term borrowing.
Finally, I don't think Clintonism, or the absence thereof, holds the answers to big problems like the auto industry. First, we were told Mr. Obama wanted a bailout, while Mr. Bush insisted on a swap for Columbian Free Trade. Then, we saw polls showing just 30% support for the UAW . . . oops, I mean, the automakers generally, so in response we are going through a cycle of ritualistic (and pointless) humiliation for the executives because they fly on company planes. Detroit is now preparing for something like the Poor People's March of 1968, with vendors, workers, and executives all riding proverbial mule trains to Washington to sit in the mud and beg for money, in advance of their December deadline. It will take more than coolness -- or Clintonism -- for Mr. Obama to get this one right.