Young Mr. Obama

by Edward McClelland

  VOICE-OVER: Barack Obama, Democrat for Congress. New leadership that works for us.

  OBAMA: Paid for by Obama for Congress 2000.

  Primary day is always cold in Chicago, but Obama stood dutifully in front of elementary schools and park field houses, shaking hands with voters. He cut a lean, handsome figure in his black topcoat and gray scarf. Over and over, the old ladies shuffling to the polls told him the same thing: “You seem like a nice young man, but Bobby hasn’t done anything wrong.”

  If Obama had known in his bones that he was going to lose, now he was hearing the bad news to his face. The local TV stations called the race even before Obama arrived at his Election Night party. The final tally was 61 percent for Rush, 30 percent for Obama, and 7 percent for Trotter. Obama barely won his own neighborhood, taking 55 percent of the vote in Hyde Park.

  “There’s no more difficult play in politics than running against an incumbent,” Obama told his supporters in a concession speech at the Ramada Inn Lakeshore. “I think we did it very well.”

  But later, talking to a reporter at the party, Obama sounded fed up with politics. He wasn’t sure whether he’d ever run for office again.

  “I’ve got to make some assessments about where we go from here,” he said. “We need a new style of politics to deal with the issues that are important to people. What’s not clear to me is whether I should do that as an elected official or by influencing government in ways that actually improve people’s lives.”

  Obama was dejected, demoralized, and bitter about his opponents’ personal attacks.

  “Me being president of the Harvard Law Review, I never thought it could be a liability,” he told Jesse Ruiz, “but it was a liability in this race.”

  Obama didn’t lose because he was “too white.” He lost because he was a presumptuous young man challenging a popular incumbent. If anything, his whiteness spared him a bigger beating. He ran strongly in Beverly and the southwest suburbs. Obama also hemmed and hawed too long before committing himself to the campaign, and once he was in, he didn’t devote enough time to building a grassroots organization or raising money. Calling his Harvard classmates was no substitute for cultivating donors on the South Side.

  Winning the seat in the historic First Congressional District would have added Obama’s name to a lineage of powerful black leaders: Oscar DePriest, William Dawson, Ralph Metcalfe, and his own political inspiration, Harold Washington. It would also have put him in line for the job he had coveted ever since arriving on the South Side: mayor of Chicago.

  Defeat always smarts for a politician, especially one who has never before failed at anything.

  It stung Obama to have his credentials as a black man questioned, and it stung him even more to lose. But in losing, he absorbed a lesson that would carry him far higher than he could have risen as the First District’s congressman. Obama was never meant to be a voice of black empowerment, in the way that Rush and Jesse Jackson were. It wasn’t just a racial thing. It was generational, too. Confrontational sixties-style politics were not his bag. With his biracial heritage, Obama was born to reconcile the interests of blacks and whites. He tried to sell that message in 2000, but he was running against a civil rights icon in the blackest congressional district in America. It was the wrong race, and the wrong time, for the emergence of Barack Obama.

  The week of his defeat, Obama returned to Springfield, where he sat down to his regular poker game at Terry Link’s house. The same words were on the lips of every pol at that table: “I told you so.” Obama didn’t need to hear it. He knew he’d blundered.

  Around that time, Obama also had a soul-searching drink with Rich Miller, the publisher of Capitol Fax, a Springfield newsletter. During the campaign, Miller had told me, “Barack is a very intelligent man, but he hasn’t had a lot of success here, and it could be because he places himself above everybody. He likes people to know he went to Harvard.”

  Obama was upset about the way Miller had characterized him, but “he took that criticism the right way,” Miller would remember years later.

  “A lot of politicians, they know that they’re smart,” Miller said. “They know that they’re capable. It messes with their minds. Politics is not a game of qualifications. It’s a game of winning. That congressional campaign really showed that to him.”

  Losing that race helped Obama in another way: It humbled him. Before his encounter with Bobby Rush, Obama was a cocky young pol in a hurry. He needed the deepening experience of defeat to learn who he was as a politician. It wouldn’t be enough to present himself as Barack Obama, first black president of the Harvard Law Review. He was going to have to stand for something, too.

  After the primary, Obama was broke—he had neglected his law practice for six months—and he was persona non grata in a party that had closed ranks around Rush. That summer, Obama flew to the Democratic National Convention in Los Angeles, at the urging of friends who still believed he had a political future. When he landed, he had trouble even renting a car. Hertz rejected his American Express card. Obama eventually got his car but then couldn’t get a pass for the convention floor. Sorry, the chairman of the Illinois delegation told Obama. I’m getting a ton of requests. So Obama watched the speeches on TVs in the Staples Center concourse. Once in a while, he sneaked into a skybox by tagging along with friends. Lesson: In Chicago, you wait your turn, young man. Dispirited, Obama returned home before Al Gore was nominated.

  Chapter 10

  “I’LL KICK YOUR ASS RIGHT NOW”

  A F T E R H I S F A I L E D C A M P A I G N against Bobby Rush, Obama’s reputation in the black political community was worse than ever. First, this young punk had knocked a little old lady schoolteacher off the ballot and taken her senate seat. Then, he’d tried to beat an incumbent congressman who’d been marching in the streets for civil rights when Obama was a kindergartener in Hawaii.

  On Election Night, Rush called Obama and Trotter “very important individuals” and invited them “to work together on the issues that are of concern to the residents of the First Congressional District”: “Let’s work on the transportation issues. Let’s work on the health issues. Let’s work on the economic development, and I think we can accomplish a lot together,” he said.

  Those were just the words of a winner who wanted to sound gracious in the press. In reality, Rush had developed a deep grudge against Obama. Rush had mortgages and children in college, and Obama had tried to take away his livelihood. (Of course, Rush himself had won the seat by beating an elderly incumbent in an election that was also about generational change, from the preachers and funeral directors of the civil rights era to the militants of the black power movement.) When the congressional districts were redrawn after the 2000 census, Obama’s condo was a few blocks outside the First District. Rush claimed he’d had nothing to do with the gerrymandering, which divided Hyde Park between himself and Jesse Jackson Jr. Obama pretended not to care, telling the Tribune he had no plans to run for Congress again.

  In fact, Obama was thinking of quitting politics altogether. During what friends would call his “pity party” after losing to Rush, he almost accepted a job as executive director of the Joyce Foundation. He didn’t want to leave politics, he told Ab Mikva, but it was a six-figure job, and Michelle was worried about the family’s finances, especially since the congressional campaign had put the Obamas even deeper in debt. The Joyce Foundation had supported the Developing Communities Project, so it was a place where Obama could work to improve the inner city, maybe more so than a politician could. If he couldn’t beat Bobby Rush, how was he ever going to get out of the state senate?

  Mikva urged Obama to stay in the legislature. If he couldn’t afford to do that, Mikva said, he should take the professorship the law school was pushing on him. That would pay as well as the foundation and offer more freedom to keep his hand in politics.

  Obama spent the first few months after the primary stewing over his defeat. Once he got over it, he realized that if he was
going to have a political future, he would have to repair his relationship with the black community. Bobby Rush’s crowd—the nationalists, the militants, the folks who wanted to rail against the white man—would never embrace him now. During the campaign, Obama had made it clear he considered their brand of politics self-defeating.

  “On issues of job creation, education, health care, we have more in common with the Latino community and the white community than we have differences,” he’d said. “And we have to work with them, just from a practical political perspective. It may give us psychic satisfaction to curse out people outside the community and blame them for our plight, but the truth of the matter is if we want to get things accomplished politically, then we’ve got to be able to work with them.”

  There was a segment of black Chicago that was ready to hear Obama’s vision of pan-racial politics: the business community. Although Obama was not wealthy—at best, the family was upper-middle-class—he already socialized with members of the city’s black bourgeoisie. John Rogers was a close friend, as was Marty Nesbitt, a vice president of the Pritzker Realty Group. (Nesbitt’s wife, an obstetrician, delivered both of Obama’s daughters.) Obama was also a member of the East Bank Club, a downtown gym/networking salon popular with Chicago’s professional class. He played pickup basketball with Jim Reynolds, CEO of Loop Capital Markets, an investment banking firm. Reynolds knew only that Obama was a state senator, which wasn’t enough to impress him. Then, one day, he was browsing at Borders and found Dreams from My Father in the discount bin. Surprised that one of his basketball partners had written a book, Reynolds bought a copy. The next time he saw Obama on the court, Reynolds mentioned Dreams.

  “Hey, you know, I read your book,” he told Obama. “You’re a pretty good writer. You had an interesting background.”

  “Well, I know I’m a good writer!” Obama shouted back.

  After that, Obama and Reynolds became regular teammates. They also met up for golf at the South Shore Country Club, where Obama always won by keeping the ball in the fairway and hitting no errant shots. When Reynolds was in Springfield, he used Obama’s state senate office as his own.

  Reynolds, who was one of the buppies on the Obama for Congress finance committee, also helped Obama plot his next political move: a run for the U.S. Senate. On the night Obama lost to Rush, Reynolds tried to buck up his friend by assuring him there would be other races, for bigger offices.

  “Hey, man, don’t feel bad,” he told Obama. “Let’s figure out what we’re going to do next.”

  It wasn’t long before they did. Obama and Reynolds sat down with Marty Nesbitt and ran through the list of statewide offices. Attorney general would be open in 2002, but Obama’s fellow state senator Lisa Madigan had her eye on it. And Madigan was the daughter of the state’s most powerful Democrat, House Speaker Michael Madigan. The Senate looked more promising. The Republican incumbent, Peter Fitzgerald, was seen as a one-term fluke. Fitzgerald had not so much beaten Carol Moseley Braun (herself a one-term fluke) as been in the right place to benefit from her missteps. Once in office, he alienated his party by appointing a U.S. attorney from out of state. Unfamiliar with the Chicago Way, Patrick Fitzgerald (no relation) prosecuted corrupt Republicans and Democrats with equal ardor. Senator Fitzgerald had even tried to block funding for a new Lincoln museum in Springfield, figuring it was just pork for Governor George Ryan and his lobbyist pals. As a result, he had no friends in the Illinois GOP, and the word was he would either step down or face a primary challenge from a Republican more willing to play the game.

  Reynolds began bringing Obama to meetings of the Alliance of Business Leaders and Entrepreneurs, an all-black business group that met for a monthly luncheon at the Chicago Club. Obama was one of the few politicians among a crowd of investors, bankers, publishers, and attorneys. Whenever anyone questioned his presence, Reynolds made one thing clear: “If you want to be a friend of mine, you have to be a friend of his.” While Obama never gave a speech at the ABLE meetings, he was meeting people whose money he would need to run for higher office.

  Chicago’s black business community has a history as long and rich as that of its black political class. Like the politicians, the entrepreneurs got their first opportunities because of segregation. Whites wouldn’t bury blacks or sell them life insurance policies, so storefront funeral parlors and insurance offices sprang up in the ghetto. Whites couldn’t cut African hair, so blacks opened their own barbershops and beauty parlors. The downtown dailies ignored life in the Black Belt (Tribune editors ordered reporters not to write “blue” news—a code word for African-American.) So blacks communicated with each other through their own network of newspapers, magazines, and radio stations.

  Some of America’s first black millionaires were Chicagoans, operating businesses that catered only to other blacks. John H. Johnson published Ebony and Jet magazines from a Michigan Avenue office tower that now bears his company’s logo. Ed Gardner sold his Soft Sheen and Ultra Sheen hair care products in drugstores across the nation.

  In Chicago, business and politics are inseparable. Wealthy blacks have always been expected to contribute a share of their fortunes to black politicians. In return, they benefit from pinstripe patronage, the practice of handing out big government contracts to big political donors. And, of course, some of that big money ends up back in the campaign funds of the politicians who handed out the contracts.

  When Harold Washington was running for mayor, he was backed by the city’s black grocers, auto dealers, undertakers, and tavern owners. Once he got into office, he tried to create a new class of black professionals by cutting his people into city business that had once been reserved for the Irish and the WASPs. Washington made sure that blacks got a bigger share of city contracts than they’d received from white mayors. This was a huge boon to black developers and contractors. Once they’d proven they could build a school in the city, why couldn’t they build a shopping center in the suburbs? The mayor also made it clear that he would steer more of the city’s lucrative bond counsel business to law firms with black partners. Maynard Jackson, who later became mayor of Atlanta, was then a partner with Chapman and Cutler, the city’s premier bond firm. After Jackson left to start an Atlanta office in the mid-1980s, the firm needed another black bond lawyer to stay on city hall’s good side. It trained a young partner named Stephen Pugh, who eventually started his own public finance law firm, Pugh, Jones, and became an ABLE member.

  Washington’s campaign to bring blacks into traditionally white businesses was so important because black entrepreneurs had actually been damaged by the civil rights movement. Once blacks could shop downtown at Marshall Field’s, they didn’t need the clothing boutique on Forty-seventh Street. Once they could go to the show at any movie theater, the neighborhood picture palace shut down (or started screening kung fu or porno movies). Black dollars were leaving the community, but white dollars weren’t coming in. The next generation of black millionaires couldn’t depend on the ghetto trade; they would have to do business with all races.

  As a state senator, Obama was valuable to the members of ABLE. Along with Emil Jones (who was also invited to ABLE meetings), he worked to open up the state’s pension fund to minority investment firms.

  “We wanted to, as black businessmen, have a relationship with everybody, so they would know our needs and where we were coming from, and be responsive to us,” Pugh would say. “In the public finance area, I’m sure that as he went down and looked at the deals that were coming through the state, he made sure that firms like Pugh, Jones were at least put on the list so that we could bid or be selected if we won the competition. It was never a thing that I knew him to say, ‘Pugh, Jones needs to get this next bond deal.’ Nothing like that. But the state workers knew we were out there. There were people like Emil who were making sure that they just didn’t ignore, as they had in the past, minority business in the process.”

  However Obama and Jones worked, Pugh, Jones got more business from the st
ate of Illinois. In 2002, Pugh’s firm was involved in a $10 billion bond deal to support the state retirement system. It also worked on a deal to privatize the state lottery. When the time came, Pugh would find a way to help Obama in return.

  During the congressional campaign, Obama had been caricatured as an ineffectual state senator, a man so consumed with his own ambition, so eager to use Springfield as a stepladder to Washington, that he didn’t bother to learn the ins and outs of legislating. Despite his success with welfare reform and child support, Obama was still seen as an idealist who thought cloakroom negotiations were beneath his dignity.

  When Obama returned to the capitol, he began taking his work—and his colleagues—more seriously. Before, he’d been a résumé in search of an office. Now he was determined to make a name for himself on issues important to his urban district. Some senators thought that Obama had been humbled by his loss to Rush. Donne Trotter didn’t quite see it that way. He had to admit his fellow senator was working harder, but humble? Barack Obama? Obama was a competitor, and competitors don’t like to lose. The once-impatient young man immersed himself in the legislative process, learning the “get-along” qualities necessary to pass a bill. No longer a loner, Obama was taking advice from colleagues he’d ignored during his first four years.

  Obama, Trotter, and Rickey Hendon cosponsored a racial profiling bill that would have required police to record the race, age, and gender of every driver they pulled over. (It never got out of the Judiciary Committee.) Obama also argued, unsuccessfully, against a bill that made gangbangers eligible for the death penalty if they committed a murder as part of gang activity. It’s never popular to look as though you’re sticking up for the Vice Lords, so Obama voted “present” on the bill, but only after insinuating it was racially motivated.