It is not farfetched to believe that Barack Obama has spent pretty much his entire 50 years trying to make people who find him fearful comfortable. Even his white grandmother admitted to being nervous if an African American male approached her, an attitude that could not help but affect him in his impressionable years. Add to that someone who appears constitutionally conflict-averse (his pre-politician career as a community organizer was to get people to work together, not fight it out), and you have the makings of a person ill-suited for the divisive environment of Washington and the full-contact political battles that have to be fought.
And we've seen that tendency manifest itself as a politician who is always willing to bend over backwards to those who will not trust him, whether from their own innate racism or from their own personal agenda. There's no question that racism plays a much greater role than liberal white America may have wanted to acknowledge, although our minority friends and colleagues would probably say "duh!". One little moment of expressed irritation will give rise to literally hundreds of thousands of reports in the media and right wing blogs/publications/foundations of the angry black man. So rather than play to those disposed to give him the benefit of the doubt, Obama rather tries to win over those who will never do so.
Do you know what I want in a president? I want for once someone who's worked on his childhood issues in a therapist's office instead of feeling he has to do it on a national stage.