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I can understand how some people think he's "elite" and "arrogant", but arrogance usually comes from feelings of insecurity and I think that's the least of Obama's characteristics
On issue after issue, Preckwinkle presented Obama as someone who thrived in the world of Chicago politics. She suggested that Obama joined Jeremiah Wright’s Trinity United Church of Christ for political reasons. “It’s a church that would provide you with lots of social connections and prominent parishioners,” she said. “It’s a good place for a politician to be a member.” Preckwinkle was unsparing on the subject of the Chicago real-estate developer Antoin (Tony) Rezko, a friend of Obama’s and one of his top fund-raisers, who was recently convicted of fraud, bribery, and money laundering: “Who you take money from is a reflection of your knowledge at the time and your principles.” As we talked, it became increasingly clear that loyalty was the issue that drove Preckwinkle’s current view of her onetime protégé. “I don’t think you should forget who your friends are,” she said.
Others told me that Preckwinkle’s grievances against Obama included specific complaints, such as his refusal to endorse a former aide and longtime friend, Will Burns, in a State Senate primary—a contest that Burns won anyway. There was also a more general belief that, after Obama won the 2004 United States Senate primary, he ignored his South Side base.
Ivory Mitchell, who for twenty years has been the chairman of the local ward organization in Obama’s neighborhood—considered the most important Democratic organization on the South Side—was one of Obama’s earliest backers. Today, he says, “All the work we did to help him get where he finally ended up, he didn’t seem too appreciative.” A year ago, Mitchell became a delegate for Hillary Clinton.
Preckwinkle, and eventually she signed on as an Obama delegate. I asked her if what she considered slights or betrayals were simply the necessary accommodations and maneuvering of a politician making a lightning transition from Hyde Park legislator to Presidential nominee.
“Can you get where he is and maintain your personal integrity?” she said. “Is that the question?” She stared at me and grimaced. “I’m going to pass on that.”
“This administration has managed to divide its friends and unite its enemies,” said Steve Clemons, director of the American Strategy Programme at the New America Foundation.
He and others lay the blame on the Chicago team, advisers from Obama’s adopted city. “Obama’s West Wing is filled with people who are in their jobs because of their Chicago connections or because they signed on early during his presidential campaign,” complained Doug Wilder, who in 1990s Virginia was America’s first elected black governor and was an early backer of Obama. “One problem is they do not have sufficient experience at governing at the executive branch level. The deeper problem is that they are not listening to the people.”
Obama relies on five people, four of whom are Chicagoans. They are Rahm Emanuel, his chief of staff, David Axelrod and Jarrett, his political advisers, and Michelle, while the fifth kitchen cabinet member is Robert Gibbs, his chief spokesman, who comes from Alabama.
The president consults them on everything. Military commanders were astounded when they participated in Afghanistan war councils and referred to them as the “Chicago mafia”. It was this group that inserted into Obama’s Afghan surge speech the deadline of July 2011 as a date to start withdrawing.
The biggest hurdle may be Obama’s own ambition combined with lack of experience. A leading Democratic supporter described his administration as “unfocused”, adding that he had counted 137 items on Obama’s agenda.
“He needs to realise that he’s running a huge operation and has to sequence priorities,” said Clemons. “He’s not thinking like the chief executive of a complex organisation.”