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I agree that Kerry always made sense, eventually. He would come up with these wonderful baroque constructs full of curli cues and interjections, and qualifiers, and, and, and. He's very thoughtful.
Sometimes he needed to just say "Yes". And stop. So I think his speaking style hurt him among the non Henry James crowd (approximately everybody in America except for a handful).
Obama is just on another level. He can build complex passages, but it's not like being on Mr. Toads Wild Ride while you are listening to him.