I've been reading The Obamas and one thing that strikes me is the extreme bubble that the President lives in. Looking back at what I know of Obama, I think that this has been a defining trait of his life.
His childhood must have been difficult. He started as the son of a white woman and an African at a time when mixed race couples were shot at in some states (it happened to a friend of mine). His father abandoned him and his mother moved to Indonesia and married again. Obama's childhood alternated between of being a foreigner and being a black man raised by whites. Where most blacks in America are descended from slaves, Obama was descended from slave owners.
According to Dreams From My Father, by high school, Obama found a Marxist mentor. In college he says that he didn't have time for anyone except Marxists and radical feminists.
Obama worked for for a private company for a short time and felt like an outsider. He felt like an infiltrator. This antipathy to for-profit employers continues to show up in his speeches.
He spent two years as a community organizer but ultimately was a failure at it. He got his law degree and ran for office. He eventually settled in as a part-time college teacher and state senator. He disliked the Illinois Senate.
After being elected to the US Senate, he discovered that he didn't care much for it either. Several times The Obamas mentions Obama's low regard for Congress and politics in general.
After being elected to the US Senate, the Obamas decided that they would not make any new friends. They worried that new acquaintances would be false friends who were actually advancing an an agenda. They continued this trend after Obama's election to the presidency, actually pulling back on the number of friends they were still in contact with.
So, where does this leave us? All of his adult life Obama has shunned people with conflicting opinions. He is dismissive of them as shown in his speech about bitter clingers.
Obama came to office convinced that any problem could be solved by getting intelligent, well-meaning people to talk to each other. Eventually they would come to a compromise. He was shocked to find that this does not happen. Even within his own cabinet, people will become more fixed on their opinion instead of open to compromise.
Since he was never exposed to dissenting views, Obama tends to see them in the worst possible light. Republican opposition is not based on principled views, it is a cynical attempt to ruin his presidency. Tea Party opposition must be racially motivated.
This has hobbled his Presidency. He fully expected that a well-meaning outreach to countries such as Russia and Iran could reset relations.
During the Gulf Oil Spill, Obama's distrust of executives meant that the spill was going on for weeks before he ever talked with the head of BP.
Other presidents regularly socialized with Congress. Bush invited Congressional leaders to the White House regularly. So did Clinton This served him well when dealing with then-Speaker Gingrich. Newt said that he always "melted" in Clinton's presence and took a couple of days to recover.
In contrast, Obama does not socialize with Congress. It was a front page story when he played golf with the new Republican Speaker. Once.
The result of this is that not even the Democratic leadership in DC really cares for Obama. Reid and Pelosi distrust him. The circle of advisers he trusts keeps getting smaller and smaller and the remaining ones are reluctant to tell him what he needs to hear.
Ironically, Michelle Obama once worked in the Chicago Mayor's Office but left in disgust because he relied on such a small circle of advisers. Now, years later, Michelle and her husband are in the same position.