In order to understand the Obama reelection campaign you have to keep in mind that it is taking its cues from President Obama himself. There are several traits that the President has that have manifested themselves in the campaign.
First, Barrack Obama is a jerk. Insider accounts such as The Obamas say that he is ultra competitive. It is possible that Obama is only running for reelection because leaving when he could run again would seem like losing. According to numerous accounts, he loves the privileges of the presidency but he and his wife hate the actual job.
Obama is a poor loser. He sulks. He pouts. Worse, he is a poor winner. When he wins he gloats. He rubs in in peoples' faces.
Obama also is a bit of a bully, at least verbally. Just listen to his speeches. Remember the "car in a ditch" speech? He loves to reduce his opposition to an easily-mocked caricature.
Obama has an unparalleled appreciation for his own talents and abilities. When Obama was interviewing people for cabinet positions he told at least two applicants that his big problem was that he could do everyone's job better than anyone he could appoint. He really does thing that he is the smartest person in Washington and that he has special insights that no one else shares. He doesn't even try to understand other viewpoints because he already knows that they are wrong. When the Tea Party started opposing Obama's policies the left declared that they could not possibly have a valid point of view so it must be racism. Obama never publicly said this but insider accounts indicate that he shared that view.
Because Obama is so convinced in his own innate superiority, it does not occur to him that people let him win basketball games. For his 50th birthday, he put together a mini-tournament of politicians and professional basketball players. He personally chose the teams (giving himself an edge). People who were there indicated that he seemed to think that a 50-year-old amateur could match a professional ball player.
This goes hand in hand with Obama's dislike of politics and compromise. When they moved to DC, the Obamas decided that they would not make any new friends because everyone in DC has an agenda so they couldn't trust any new friends. Where LBJ used games of golf as an opportunity to lobby the opposition, Obama only golfs with staffers so that he can get away from politics.
Obama is ideological. When he was in college he was a dedicated Marxist. At some point he moderated his views but he still has a Marxist tinge to his world-view. That is why he looks at current earnings instead of wealth when defining the rich and why he has so consistently insisted that raising taxes on the rich is justified in the name of fairness.
Finally, Obama hates Mitt Romney on a personal level. I've seen some speculation on why. It might be his dislike for the rich. He might the fact that Romney was brought up in a traditional family while Obama's mother divorced his father and step father and finally sent him to live with his grandparents.
Put it all together and you have a someone who will do anything to win and who hates his competition. Is it any wonder that his campaign staff is willing to throw any and all dirt? They probably don't even see it because they are so convinced of the rightness of their cause.