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Ronald Reagan, for one, managed to use his landslide victories to get his policies made into political reality. If we have a candidate with crossover appeal-- and Obama has far more than Clinton-- we have a chance to get something done. It really is that simple.
And while I'm here-- if you want a case where Obama's more progressive than Clinton here's one: He supports full repeal of the Defense of Marriage Act, and Clinton does not. That's a big one to me.