Obama in particular embodies that common thread between my community and his by being (again from Samuels) "a self-made man, part con artist, part performer, living in an imaginary future that will make him and his audience whole."
The flip side is that, truly unlike any potential president since the early days of the Republic (except Lincoln, maybe), he is a person of the book, and of books, and of philosophy and literature. If he does get to be president, his memoirs will be vastly more penetrating in their insights than anything a president has produced since Ulysses Grant more than a century ago, and radically unlike any president's literary output since presidents stopped writing for themselves sometime last century. That literariness is balanced by an Ivory Tower-trained analytic intelligence --- as the Clinton campaign found out to their chagrin, he was in fact a fairly skillful and accomplished legal academic.
All of which means that if elected, Obama will be the first president in ages (if not ever) to suffer from what Joyce called the agenbite of inwit (from ME, meaning "remorse of conscience"), the near-universal soul-sickness of introspective literary and intellectual types in the modern age, grasping for and unable to find concrete, stable concepts of identity and historical progression by which to gain a foothold on their world.
The condition is a two-edged sword for scores of reasons. For example, on the positive side of the ledger, it can provide fuel for empathy, for a creativity in problem-solving, and for just enough misanthropy to motivate the enlightened governance that rejects crude, short-sighted populism (his stand against the gas tax pander, his connections to and education from people like Austan Goolsbee and Lawrence Lessig are the encouraging data points here). And on the negative side, consider that Woodrow Wilson was the closest precedent in this regard, and one of the worst presidents we've ever had, and Jimmy Carter and Richard Nixon are next closest. Intellectuality, especially when self-aware, can be a straitjacket and an amplifier for mistakes.
But more to the point here, the agenbite is, if not a Jewish condition, then more pervasive among Jews than any other group, by a wide margin. (It was no accident that Buck Mulligan described Stephen Dedalus as "a jesting jew jesuit," nor was it coincidental that the greatest song ever written about the suffering and dispossession of American southerners in the Civil War was written by a half-Jew half-Mohawk from rural Ontario.) Virtually every significant feature of Obama's biography --- from his name, to his twice-over paternal abandonment, to the clash of skin colors with all his relatives, to his drug years, to his Ivy League education, to his admission to modern day Talmud study in a law faculty --- scream of the agenbite, and through it, to a connection with the experience of overwhelming numbers of post-Haskalah Jews (which may or may not come to the same thing as the Jewish experience).