I found this yielded some insight into why Obama thinks he can just cruise to victory in November:

“After his loss in the 2000 Congressional primary race to former Black Panther Bobby L. Rush, “colleagues noticed that he seemed exhausted and was smoking more than usual,” and they offered him a tenured faculty position (with a job for his wife). Think about that! He never produced a word of legal scholarship, after all those years teaching, and now they would simply give him tenure — at the University of Chicago Law School, a top 5 school, where the faculty is known for voluminous scholarly publishing. The case for tenure in law school depends predominantly on scholarship. You don’t get tenure for being a very popular teacher. The failure to publish anything should be fatal to the tenure case of a lawprof who was hired with a belief in his promise as a scholar, but here tenure is bundled into the original offer to someone who had demonstrated that he lacked that promise… It would be cruel to say that Obama was filling a quota at the University of Chicago, cruel, but not entirely inaccurate.”

The honors and positions awarded him in the past were basically handed to him for being cool and (part) black. Looking at today’s campaign he apparently believes this year will be no different.