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In Obama's circle, Chicago is the tie that binds

Sen. Barack Obama's closest friends today are a biracial cross section of Chicago's business and professional elite.
Image: Barack Obama, Valerie Jarrett
Democratic presidential hopeful, Sen. Barack Obama, D-Ill., and his senior advisor Valerie Jarrett, second from left, sit in a campaign train near Wayne, Pa., in april.Jae C. Hong / AP file
/ Source: a href="" linktype="External" resizable="true" status="true" scrollbars="true">The Washington Post</a

For once, Barack Obama left his iPod and stack of news clips at his seat and worked the front cabin of his campaign's chartered plane, laughing and reminiscing with the people who know him best.

The senator from Illinois does not typically travel with an entourage, instead spending his time on the plane reading, working or listening to music. But this was a special occasion -- the night last month when he was claiming the Democratic presidential nomination. Joining him and his wife, Michelle, for the flight from Chicago to St. Paul, Minn., were half a dozen of their closest friends, a biracial cross section of the city's business and professional elite: Martin Nesbitt, a parking lot magnate; Valerie Jarrett, a prominent businesswoman; Eric Whitaker, an executive at the University of Chicago Medical Center; and John Rogers, the founder of an investment fund.

Some were mainly social friends from Hyde Park, their Chicago neighborhood. Some have played a major role in Obama's campaign, including Penny Pritzker, a billionaire Hyatt hotel heiress and Obama's national fundraising chairman; James Crown, son of Chicago billionaire Lester Crown and another prominent member of the local Jewish community; and David Axelrod, who has been Obama's Chicago-based political adviser and confidant since his U.S. Senate campaign in 2006.

Together they constitute the core of Obama's inner circle, the friends he had before he became a senator and entertained thoughts of the presidency, and who he would bring with him in a sense if he ends up in the White House. "There are a lot of people with shared values," said Nesbitt, whose family vacationed with the Obamas over Easter and whose daughters spend most Saturdays together.

Like Nesbitt, most were present at the creation of Obama's long-shot presidential bid. They have opened important doors for him, given him counsel and bad news, and demonstrated a low-profile loyalty that has set the tone for his campaign. They also have taken to heart the two rules Obama has imposed on everyone associated with his presidential bid, whether old friend or new hire: "no drama" and "no leaks."

"He's going to gravitate toward people like him," said Jarrett, who also serves as a senior campaign adviser and is one of the code's quiet enforcers within Obama's world. "He's going to look for people with similar temperaments."

One campaign aide described Jarrett's loosely defined role as liaison between Obama's private life and campaign life. In meetings, she will weigh in when an idea "doesn't sound authentically Barack," as one campaign aide put it. She also will quietly smooth internal riffs and other disruptions.

Whitaker goes back the furthest with Obama, having met the idealistic community organizer during their student days at Harvard. They shared a drive to reverse troubling patterns in the African American community. A public health specialist, Whitaker founded "Project Brotherhood," a barbershop-based program aimed at improving the health of black men, and served as a senior physician at Chicago's Cook County Hospital, now known as John H. Stroger Jr. Hospital.

Pritzker and Crown have played instrumental roles in building Obama's huge campaign war chest, but their prominence has also provided him a pathway to Jewish voters. Speaking at a synagogue in Boca Raton, Fla., in May, Obama called Pritzker and Crown "dear friends" from "pretty prominent" Jewish families, and told the crowd: "One of the raps on me when I first ran for Congress in the African American community was, 'He's too close to the Jewish community.' You can look this up. 'All his friends are Jews. He's from Hyde Park; he's from the University of Chicago.' "

Nesbitt fits into several circles. As the campaign's treasurer, he plays a lead fundraising role. "Barack said, 'I want to run this like a business,' and I've tried to help do that," he said. Nesbitt also shares Obama's passion for basketball and is a member of a travel team that includes Whitaker; Rogers, who founded Ariel Capital Management, the country's first black-owned investment firm; Alexi Giannoulias, the Illinois state treasurer, who played professional ball in Greece; and Reggie Love, Obama's 26-year-old "body man" and a kind of surrogate son, who played basketball and football at Duke University, and who is one of the few mainstays on the court without Chicago ties.

While Love adds levity, Jarrett and Nesbitt provide a needed reality check from time to time. The two can raise issues with Obama that campaign aides are reluctant to broach, such as, 'You're dragging and people are noticing" or "Don't be so curt."

Last spring, as gasoline prices were beginning another precipitous rise, Nesbitt made sure his friend understood what was happening. "In case you're not living in the real world, being driven around by Secret Service," his e-mail to Obama said, "it just cost me $85 to fill up my tank."

Axelrod said that "it's helpful to have people who the candidate trusts, where you know anything they say is going to be motivated by their concern for you."

But it's a role that Obama's friends sometimes take more seriously than he does. "Every now and then, someone will send me on a mission because he needs to be told something that only I can tell him," Nesbitt said. "I'll say, 'Hey, you know, they think you should be doing this.' " And Obama will respond, "You are just so transparent." Nesbitt added: "When he knows we're just trying to cheer him up or pump him up, he'll just start laughing."

Diverse profiles
Obama's world includes other circles of friends and advisers, many of whom remain little known to the public but who share the candidate's discretion and intense sense of commitment -- and whose reward is to rise along with him.

One group is connected to Obama through Harvard Law School and includes economic adviser Michael Froman; domestic policy adviser Cassandra Q. Butts; and Julius Genachowski, who engineered Obama's cutting-edge campaign technology. Two of Obama's most prominent Harvard professors, Laurence H. Tribe and Charles J. Ogletree, continue to provide guidance on legal issues.

Obama's core foreign policy team is an eclectic mix of 40-somethings, such as former assistant secretary of state Susan E. Rice, veteran diplomats such as Anthony Lake; Senate aides Denis McDonough and Mark Lippert; and prominent military experts such as Clinton administration Navy secretary Richard J. Danzig and retired Air Force Maj. Gen. J. Scott Gration. Gration, the son of missionaries in Congo, speaks Swahili and voted for George W. Bush in 2000, but he fell for Obama when the two traveled to Africa together in 2006. For help on the Middle East, Obama turns to longtime Chicago friend Lee Rosenberg, an entrepreneur and board member of the American Israel Public Affairs Committee, a Jewish lobbying force.

Obama has collected a core of Washington insiders, including prominent lawyers Greg Craig and Eric Holder; former Senate majority leader Thomas A. Daschle (S.D.), and former congressman Timothy J. Roemer (Ind.). Sen. Edward M. Kennedy (Mass.) and his niece Caroline Kennedy also are close to Obama; Caroline Kennedy and Holder are leading the campaign's vice presidential vetting team.

Despite their diverse profiles, Democratic establishment types who gravitated early to Obama share his distaste for the divisive, personality-driven culture of today's Washington. "He is a sincere, down-to-earth, in-touch person," Roemer says. "It's just not that common in politics today."

Another important group in Obama's life consists of the Chicago progressives who have mentored him throughout his career. The leader of this group is Abner J. Mikva, a retired federal judge, White House counsel and congressman from Chicago who has known Obama for 20 years, and who often is described as a father figure to the senator.

Mikva has quietly helped guide Obama since his Harvard Law School days. He encouraged his political aspirations, was an early advocate of his presidential run and has pulled numerous strings to help to ease the candidate's path.

One Mikva protégé is Axelrod. A former Chicago Tribune reporter, Obama's message maestro left his home town of New York for the University of Chicago in the early 1970s and has never looked back. Like Mikva, he belongs to the city's progressive elite. Axelrod and Obama also shared a second mentor: the late senator Paul Simon (Ill.), who took Obama under his wing when he joined the state legislature.

Other members of this circle include Newton Minow, a longtime Mikva friend who hired Obama to join his civil rights law firm and whose daughter taught Obama at Harvard; Forrest Claypool, a Cook County commissioner and Axelrod partner who is a member of Obama's media team; John Schmidt, a Clinton Justice Department official who founded the reform-minded Chicago Council of Lawyers and is a member of Obama's finance team; and John Bouman, a longtime friend from Springfield, Ill., who is president of the Sargent Shriver National Center on Poverty Law in Chicago.

Obama also turns to Rep. Rahm Emanuel (Ill.), a Chicago politician through and through, who stayed neutral during the Democratic primary because of his close Clinton family ties but who endorsed the home-town candidate as soon as Obama crossed the delegate threshold. Emanuel is close to Axelrod, Pritzker and Nesbitt, and has unofficially advised Obama since he was a long-shot Senate candidate. It was Emanuel who urged Obama never to board an airplane without his iPod and something to read, telling him: "When people see those earphones, they leave you alone."

Chicago taught Obama a key lesson, Mikva noted. He was an outsider with an unusual name, but he was able to overcome those obstacles. "This is a big city, but it's a very open city," Mikva said. "People plant their flag in Chicago, and this is where they're from. You can be accepted quickly. Being here has given Barack a very large comfort zone."

The city's tentacles reach deep into his campaign apparatus, linking disparate circles by a single phone call from Mikva. In 2003, during the early stages of Obama's U.S. Senate campaign, Mikva called Lake to ask him "to talk to this guy who may not win." Lake held several briefings with the candidate and put Obama in touch with Rice, who was advising Sen. John F. Kerry's presidential campaign.

In one of their early meetings, Obama read Rice the rules: "I don't want any drama. I don't want you to bring your history or your internecine warfare." This was the political culture that Rice had been seeking, with little success. "He creates a sense of openness and security, and therefore you don't have a whole bunch of people who are needy to prove themselves to the candidate," she observed.

Cautious and protective
As Obama's campaign expands for the general-election campaign and the candidate has less time for his friendships, certain strains are starting to show. At his Chicago headquarters, insecurities have flared as the circles multiply and more people crowd inside. Jarrett said her main focus in the coming weeks will be to help the new hires integrate smoothly: "It's important that people feel good about this."

Like others who know Obama well, Jarrett has watched her friend with a certain amount of awe at the 18 months of nonstop motion and incoming fire. "You can never be fully prepared for the rigor and the discipline," she said. "The campaign itself takes some getting used to."

Obama still struggles to maintain balance in his life, especially with his family. The only time he sounds wistful is when he talks about Michelle and their daughters, Sasha and Malia, whom he often sees only on Sundays.

As the stakes get higher, Obama's friends have grown more cautious and protective -- and in some cases have attracted controversy. Whitaker's name surfaced as part of the scandal involving longtime Obama fundraiser Antoin "Tony" Rezko, because Obama had recommended his shy and studious friend to Rezko for a state job. The exchange took place after Rod Blagojevich was elected Illinois governor, and Whitaker applied for the head job at the state Public Health Department.

A Chicago developer and early Obama supporter, Rezko, acting as one of Blagojevich's liaisons, had contacted Obama to seek recommendations for state jobs. Obama singled out Whitaker, noting that he had already applied for the public health post. "I simply said, 'I think this guy is outstanding and is certainly somebody who is worthy of an interview,' " Obama told the Chicago Tribune in a lengthy interview recounting his Rezko contacts. Rezko was later convicted of federal corruption charges, and although the case did not implicate Obama, his Rezko association has caused him significant political embarrassment.

Even now, Obama reverts to his Hyde Park friends and habits whenever he has a free day. One recent Sunday, he played basketball at the neighborhood's East Bank Club with Love, Chicago public schools chief Arne Duncan and others while Jarrett chatted with Michelle Obama. Later, the family headed over to Whitaker's house for a cookout. Most of a pool report on the event was devoted to rehashing the Whitaker-Rezko link.

The exposure has made some of Obama's friends, such as Whitaker and Rogers, reluctant to speak to reporters; the two declined requests for interviews. Others try to restrict their comments to generalities and innocuous details. Nesbitt learned the perils of public exposure when MSNBC host Chris Matthews saw a clip of Obama describing his friend's gas-price e-mail and challenged the $85 cost as inflated. Nesbitt is paying even more now to fill his 22-gallon tank -- but he's too embarrassed to disclose the make and model of his luxury sedan.

Acquaintances are "reaching out" to Nesbitt, knowing that he has ready access to the presumptive Democratic nominee. He tries not to e-mail Obama often, other than the occasional "hang in there" note and complaint about onerous tax provisions. They had fun hanging out in St. Thomas over Easter, but those moments come rarely now. "He can detach for hours at a time, but it's a constant now," Nesbitt said. "He's off for a conference call or an interview or something."

He recalls telling his friend early on, "I'm so glad I'm not running for president." And Obama replied, "No, but you are."