"Obama, weaving around life’s potential barriers smoothly and largely alone, came to regard himself as not only lucky..."

"... but destined, a sensibility that could lead to overconfidence, if not hubris," writes David Maraniss, analyzing the cause and extent of Obama's problem debating Romney. Maraniss — who wrote a book about Obama — sees Obama as a man of contradictions, who "chose politics as his profession while harboring ambivalence about it."

He has played by the conventional rules yet at times betrays a disdain for the game, whether mocking the notion of sound bites or chastising the media for being slaves to a 24-hour news cycle while he thinks in the long term. 

This is in contrast to Bill Clinton, who "could immerse himself in the moment and excel at transactional politics."

Obama is more the participant-observer, self-consciously taking note of the surreal aspects of what he is doing. Clinton’s antennae were tuned to his surroundings; Obama’s are tuned to his interior being. Clinton, a brilliantly authentic phony, could assume any role the circumstances required. Obama yearns to play roles he admires. In the first debate, he was the constitutional law professor, listening, giving ground, offering complex caveats, soberly taking notes. None of that helped him.

Maybe a lawprof is not what you want in a politician. And yet, Bill Clinton was a lawprof. So was Hillary Clinton. And there are different types of lawprofs. They don't all listen, give ground, and offer complex caveats! Here's an old blog post of mine about how different Bill and Hillary were as law professors, with these quotes from Carl Bernstein's book about Hillary):

Hillary's style was confident, aggressive, take-charge, and much more structured than Bill's. "All business," a colleague said. Her questions to students were tough and demanding. Bill almost never put his students on the spot; rather, he maintained an easy dialogue with them. His conversational approach often gave students the run of the class, and he let them filibuster.

"If you were unprepared, she would rip you pretty good, but not in an unfair way," recalled Woody Bassett, who became good friends of both, and worked in many Clinton political campaigns. "She made you think. She challenged you. If she asked you a question about a case and you gave an answer, well then — here comes another question. Whereas in Bill Clinton's classes, it was much more laid-back." In class Hillary never mentioned her work on the impeachment inquiry."...

Bill was far more open about discussing political issues with his students, whether Nixon's impeachment or Roe v. Wade, on which he spent several weeks. The subject of his constitutional law course more naturally lent itself to political questions than Hillary's.

She taught — would you guess? — criminal law, criminal procedure, and trial advocacy.

He was regarded as the easiest grader in the law school. Hillary's exams were tough, and her grading commensurate with what she expected law students to know. There was little doubt that she was the better teacher, possessed with "unusual ability to absorb a huge amount of facts and boil them down to the bottom line," Bassett thought. Clinton was more likely to go at a subject in a circular way, looking at it from every angle and sometimes never coming to a conclusion. But usually his was the more interesting class, because of the passion and knowledge with which he addressed legal questions related to everyday events.

Neither of them seemed to be the Maraniss's lawprof stereotype: "listening, giving ground, offering complex caveats, soberly taking notes."