The Bridge: The Life and Rise of Barack Obama

by David Remnick

  The piece described how Rush had been able to turn the generational tables on Obama. At a debate on WVON, moderated by Cliff Kelley, Rush talked about leading a protest march in 1995 after an off-duty police officer killed a homeless man. Obama jumped in, saying, "It's not enough for us just to protest police misconduct without thinking systematically about how we're going to change practice." Rush found his opening, saying, "We have never been able to progress as a people based on relying solely on the legislative process, and I think that we would be in real critical shape when we start in any way diminishing the role of protest. Protest has got us where we are today."

  "A week later," Kleine reported, "Rush was still rankled by Obama's suggestion that the black community's protest days are past. 'Barack is a person who read about the civil rights protests and thinks he knows all about it,' he said. 'I helped make that history, by blood, sweat, and tears.'" The exchange made Obama look callow and ungrateful.

  Kleine interviewed the candidates at length and concluded that Obama spoke in "a stentorian baritone that sounds like a TV newscaster's." He also allowed Trotter to hold forth with a series of remarks that deepened the impression that Obama was insufficiently black. "Barack is viewed in part to be the white man in blackface in our community," Trotter told Kleine. "You just have to look at his supporters. Who pushed him to get where he is so fast? It's these individuals in Hyde Park, who don't always have the best interests of the community in mind."

  The article depicted Obama as being on the defensive during the campaign, fending off attacks that, to Obama, were not only offensive but reflected a tragic suspicion of higher education among some voters. Obama told the Reader that when his opponents ripped him for going to Harvard Law School or teaching law at the University of Chicago, they were sending a signal to black children that "if you're well educated, somehow you're not keeping it real." He insisted that his kind of background allowed him to live in more than one world--an essential quality for a modern politician.

  "My experience being able to walk into a public-housing development and turn around and walk into a corporate boardroom and communicate effectively in either venue means that I'm more likely to be able to build the kinds of coalitions and craft the sort of message that appeals to a broad range of people, and that's how you get things accomplished in Congress," he said. "We have more in common with the Latino community, the white community, than we have differences, and you have to work with them, just from a practical political perspective.... It may give us a psychic satisfaction to curse out people outside our community and blame them for our plight. But the truth is, if you want to be able to get things accomplished politically, you've got to work with them."

  Obama's campaign raised over six hundred thousand dollars and spent some of it on a series of three radio spots that cast Obama as the new wave, an earnest idealist tough enough to work effectively in Congress. One of the spots, written by Chris Sautter and his brother, Craig, was called "Blackout":

  MAN'S VOICE: Oh, man, there go the lights again.

  WOMAN'S VOICE: Another blackout!

  MAN'S VOICE: I'm tired of this. When's somebody going to do something?

  WOMAN'S VOICE: Obama.

  MAN'S VOICE: Say what?

  WOMAN'S VOICE: State Senator Barack Obama. He's fighting for reforms that would force Con Ed to refund customers who lose power.

  VOICEOVER: Barack Obama, Democratic candidate for Congress. As a community organizer, Obama fought to make sure that residents in Roseland and Altgeld Gardens received their fair share of services. Barack Obama. As a lawyer, Obama fought for civil rights and headed up Project Vote, registering over a hundred thousand minority voters. Barack Obama. Elected to the Illinois Senate, Barack Obama pushed to make health insurance available to everyone, regardless of income, and brought millions of dollars into our community for juvenile crime prevention.

  MAN'S VOICE: Here come the lights. Con Ed must have heard from that Senator Bama.

  WOMAN'S VOICE: That's Obama, Barack Obama. And they'll be hearing a lot more from him.

  VOICEOVER: Barack Obama, Democrat for Congress. New leadership that works for us.

  The play on Obama's name and the down-home "Say what?" had little effect. Neither did his rare appearances alongside his opponents. In debates sponsored by the Urban League and the League of Women Voters, Obama failed to draw a real distinction between himself and Bobby Rush. Obama's volunteers were encouraged by his ability to fence with Rush, but even to some allies, he seemed aloof to the point of arrogance. Obama "was kind of snotty," Toni Preckwinkle said. "His head was up in the air, he acted like he was too good to be there."

  If there were any doubts where this primary was headed, they were shelved when Bill Clinton came to town just before the balloting to campaign for Bobby Rush.

  Clinton's popularity on the South Side had only intensified during his impeachment saga. Rush had stood close to Clinton on the White House lawn after the House vote on impeachment. Clinton had not forgotten. He taped a thirty-second radio commercial for Rush that played constantly on WVON and other important stations. "Illinois and America need Bobby Rush in Congress," Clinton said, and even referred to the killing of Huey Rush to make the ad more emotionally resonant. "Bobby Rush has been an active leader in the effort to keep guns away from kids and criminals long before his own family was the victim of senseless gun violence."

  The commercial ran on March 13th and Clinton campaigned for Rush in Chicago that day, dominating local television news. "Until then, for us to win, you had to find Bobby with a live boy or a dead girl," Will Burns said. "When Clinton came into the picture, it was game over."

  On March 21st, Bobby Rush won sixty-one per cent of the vote. Obama got thirty percent, Trotter seven per cent, and a retired police officer from Calumet Heights, George Roby, won one per cent. The only area that Obama won was the Nineteenth Ward, with its Irish-Catholic teachers, firefighters, and police officers. He also scored well in the small part of the district that extended into southern suburbs like Evergreen Park and Alsip.

  The next morning, Obama went around to the houses in the district that displayed blue "Obama for Congress" signs and knocked on doors, thanking his supporters.

  In November, Rush beat the Republicans' sacrificial candidate, Raymond Wardingley, by seventy points. The last Republican to win the congressional seat in the First District had been a son of slaves, Oscar De Priest.

  Nine years after beating Obama, Rush recalled the experience with an almost unseemly relish. "Barack was not a good debater," he recalled. "He was too academic. He'd lose the crowd. And I knew something about political theater, after all. The message was simple: Where did this guy come from? Who is he? What's he ever done? ... My whole effort was to make sure that people knew that Barack Obama was being used as a tool of the white liberals. Now, these people later on also helped launch him as a candidate to the U.S. Senate and as President. You cannot deny Obama's brilliance, his disciplined approach. He is a very political guy, very calculating."

  The night of his defeat, Obama, speaking to his supporters at the Ramada in Hyde Park, said, "I confess to you, winning is better than losing."

  It was not clear that Obama would ever run for office again. Steve Neal, in a column in the Sun-Times, said that Obama would surely be heard from again--maybe he would run for Illinois Attorney General or State Treasurer--but for Obama himself even the prospect of getting Michelle's support for another campaign was forbidding. "I've got to make assessments about where we go from here," he told his supporters. "We need a new style of politics to deal with the issues that are important to the 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."

  Long after the loss, Obama recalled the sting of it: "It's impossible not to feel at some level as if you have been personally repudiated by the entire community, that you don't quite have what it takes, and that everywhere you go th
e word 'loser' is flashing through people's minds."

  Obama is not given to rages or to depression, but the loss to Bobby Rush was decisive in every way. Years later, Obama told me, "I was completely mortified and humiliated, and felt terrible. The biggest problem in politics is the fear of loss. It's a very public thing, which most people don't have to go through. Obviously, the flip side of publicity and hype is that when you fall, folks are right there, snapping away." Not only had he lost by a margin of more than two-to-one, he had been repeatedly insulted as "not black enough," as dull, professorial, effete. Was he stuck in Springfield? If Bobby Rush couldn't come close to beating Richard Daley, how could he? In addition to the professional anxieties, there were financial ones: thanks to the campaign, Obama was sixty thousand dollars in debt.

  "He was very dejected that it might all be over," Abner Mikva said, "and he was thinking how else could he use his talents." Obama began to wonder if he, and his family, wouldn't be better off if he didn't have to deal with the "meaner" aspects of political life: "the begging for money, the long drives home after the banquet had run two hours longer than scheduled, the bad food and stale air and clipped phone conversations with a wife who had stuck by me so far but was pretty fed up with raising our children alone and was beginning to question my priorities."

  Michelle Obama also had things to say post-Bobby Rush. She had been against the run in the first place and now she was wondering when her husband would settle down and figure out a practical way of reconciling his family's financial needs and the urge to contribute to the community. She did not see it in electoral politics. The family was hardly poor--their annual income was now more than two hundred thousand dollars--but the fact that they could be living immeasurably better was not lost on either of them. As graduates of Harvard Law School, both Obamas had serious earning potential, and Michelle had talked about spending all her time with the family if her husband would only tend to business. "My hope was that, O.K., enough of this," she said, "now let's explore these other avenues for having impact and making a little money so that we could start saving for our future and building up the college fund for our girls."

  Michelle Obama had long been displeased with the life of a political wife. "She didn't understand Springfield," Dan Shomon said. "She worried that he was wasting his time. He could have been making so much money and here he was mired in mediocrity." Barack was always on the move, campaigning, traveling, working in Springfield, teaching, or practicing law, but Michelle did not hesitate to make it clear that she expected her husband to do his share at home when he was there. "I found myself subjected to endless negotiations about every detail of managing the house, long lists of things that I needed to do or had forgotten to do, and a generally sour attitude," Obama wrote later in his second book, The Audacity of Hope. Dan Shomon told a reporter for Chicago magazine that Michelle said to her husband, "'O.K., Barack, you're going to do grocery shopping two times a week. You're to pick up Malia. You're going to do blah, blah, blah, and you're responsible for blah, blah, blah.' So he had his assignments, and he never questioned her, never bitched about it. He said that Michelle knows what she's doing--I trust her child rearing and the family rearing." (Sasha, the Obamas' second child, was born in 2001.)

  Obama certainly could have gone back to the University of Chicago or his law firm. Another option that he considered was leaving the State Senate and becoming the head of the Joyce Foundation, which was built on a great timber fortune and doled out around fifty million dollars a year to community projects in the city.

  "It was a sweet job--around a million a year, two country-club memberships, and I thought, Here it is, finally the day that all our hard work would pay off," said Dan Shomon, who imagined working as Obama's chief aide at the foundation. "Barack could have given out money to all kinds of good, progressive groups. He went into the interview, though, and his hands were shaking for fear that he would get the job. He knew that if he got it, that was it--he would be out of the game, out of politics."

  Obama sparkled in the interview, but, ultimately, both he and the board of directors knew that his heart wasn't in it. "For God's sake, Barack," one of the board members, Richard Donahue, said, "this is a great job. But you don't want it." Relieved, Obama promptly walked away from the foundation world.

  "That was the one thing Michelle didn't quite understand yet," Shomon said. "As much as he complained about Springfield, Barack had the addiction. And the narcotic was politics. He wanted to be an elected official. No matter what, politics completed him as a person, and he wasn't finished with it. Even when Barack was morose, when he was down and out after the race with Bobby, I never thought he would chuck politics. He had to pick up the pieces. But, ultimately, if it hadn't been for that race, there would be no Barack Obama. That was boot camp. That's what got him ready to do what he had to do."

  Chapter Nine

  The Wilderness Campaign

  A month after losing to Bobby Rush, Obama bought a cheap plane ticket and flew to Los Angeles for the Democratic National Convention, where the Party would put forward the ticket of Al Gore and Joe Lieberman. Obama was not a delegate. He had not gained much favor in the Illinois Democratic Party by trying to unseat Rush. He didn't even have a floor credential, but his friends urged him to go and make some contacts. Later, Obama realized that they were trying to get him back on the horse and have some fun.

  When Obama arrived at the airport in Los Angeles, he went to the Hertz counter to rent a car only to have his American Express card declined. He finally managed to convince a supervisor that he was good for the money. That may have been his most successful act of persuasion in months. For a couple of days, he watched speeches gazing up at a JumboTron at the Staples Center while thousands of Democrats, many of them in funny hats and all in sure possession of floor passes, streamed by him. He made his way into the skyboxes, but he could not get to the floor. He didn't stay long in Los Angeles.

  Back in Springfield, Obama endured a round of "we-told-you-so"s at his Wednesday poker game. He became even closer to Emil Jones, who told him what had been so clear from the start of the campaign. The First Congressional District was not the right political arena for him. "It was a predominantly African-American district where you had to campaign solely on those issues," Jones said, recalling his conversations with Obama. "And Barack did not campaign that way, so as a result he lost. Which was good."

  With time Obama and his small circle of political advisers and operatives began to see the value in having lost to Rush. Obama came to understand his defeat as a political education. He could not match the local appeal of Rush, who, while hardly the noblest exemplar of the civil-rights generation, boasted a historical credibility that Obama, as a man in his late thirties, could not. Rather, Obama, as a member of what he later called the Joshua generation, had a broader, more modern kind of appeal; and, because he had greater access to the elite institutions of American life, to Columbia and Harvard, to the liberals and the downtown business establishment, he had a familiar kind of education, an acceptable set of positions, a capacity to attract constituencies that Rush never would.

  "Bobby did us a favor by running the campaign the way he did--it helped define Obama," Al Kindle said. "If Obama had tried to be 'more black' or be more like Rush to beat him, and if he'd been successful, he would have been forever pigeonholed. We already knew that he wasn't a traditional black politician. The race gave him exposure. He was not Harold Washington. He wasn't Bobby Rush. He was a different leader that the community had to grow toward, white and black. There was no model for it yet. The model was the flip side of what Harold couldn't be because the city back then was too divided racially. At this point in history, the city was less overtly racist and we didn't have the same lightning-rod politicians like Eddie Vrdolyak who organized on the basis of race. Obama became the next generation."

  It was hard to imagine, in 2000 and 2001, when and how Obama's political second chance would emerge--if ever. Many in the African-Am
erican community were searching for the next generation of progressive leaders; the men and women of Rush's generation did not have the capacity to challenge Richard Daley. The situation in the Senate was not especially promising: Richard Durbin was the popular Democratic successor to Paul Simon, and Peter Fitzgerald, a wealthy young Republican, had toppled Carol Moseley Braun after a single term that had been plagued by accusations of ethical misdemeanors. When Fitzgerald's term was up in 2004, Braun could easily run again. Despite bungling her campaign finances and gaining a reputation in some quarters for low-grade corruption, she had far greater name recognition than Obama.

  After the loss to Rush, Obama and Dan Shomon started traveling around the state again in earnest. According to Shomon, between 1997 and 2004, they put in nearly forty thousand miles stopping in at dinners, country fairs, Elks-club meetings, political rallies--any conceivable event that could get him better known in the state.

  "In the car, it was just the two of us and we talked about everything, from his marriage to golf to life to women to politics," Shomon said. "A lot of it was me listening to his ideas about politics and strategy, and then I thought about how those ideas would fit into reality and how to advance him politically."

  Obama quizzed Shomon about every political player in the state. He no longer thought about running for mayor: attorney general, governor, U.S. senator---those were the offices on the horizon of his ambition now. In the meantime, he was teaching and legislating, and he even brought in some legal work to his old firm. Obama's friend the African-American entrepreneur Robert Blackwell, Jr., thought there was money to be made in Ping-Pong, what he called "the No. 1 participation sport in the world." For fourteen months, Blackwell paid Obama's firm a monthly fee of eight thousand dollars to work on contracts. (The deal became a matter of controversy when Obama, in his capacity as Blackwell's state senator, wrote a letter recommending that Blackwell's Ping-Pong firm, Killerspin, receive a tourism grant to help sponsor international tournaments in Chicago.)