The Bridge: The Life and Rise of Barack Obama

by David Remnick

  Working with health-care providers, insurance lobbyists, and other interest groups, Obama led a commission that studied expanding care to more citizens of the state. He had repeatedly expressed support for single-payer health care, but the commission was limited to modest reform. Obama, who had played poker with lobbyists and taken legal campaign contributions from insurance lobbyists, said in a debate during the U.S. Senate campaign that he had "worked diligently with the insurance industry" and with Republicans after concerns were raised about across-the-board state health coverage. "The original presentation of the bill was the House version, that we radically changed--we radically changed--and we changed in response to concerns that were raised by the insurance industry," he said.

  Jones also extracted promises from black politicians like Hendon and Trotter, who had not shown Obama much love, to endorse Obama. They agreed only after many loud discussions. "I made them an offer," Jones recalled telling Obama. "And you don't want to know."

  As he grew more experienced, Obama was also recognizing that, in order to rise in Illinois politics, in order to transcend the hermetic, somewhat independent base of Hyde Park, he needed to play ball with people higher up than Jones: in particular, with Richard M. Daley. To remain pristine in Chicago politics--to follow the path of someone like the independent alderman Leon Despres--was to put a cap on ambition. To advance, to have the means to win a statewide election, meant navigating the murky politics of Chicago. The city under the Daleys had avoided the fate of other industrial Midwestern cities like Detroit. Just as his father had built highways, O'Hare Airport, the convention center, parks, and countless office buildings, Richard M. Daley had transformed the Loop, building projects like Millennium Park, complete with its magnificent Frank Gehry-designed bandshell. Daley the Younger had been a far better mayor than his father when it came to schools, allowing more experimentation and building magnet schools and charter schools; he also leveled many of the city's horrendous high-rise projects, which housed tens of thousands of people and had become centers of gang violence. Daley showed no predilection for amassing a personal fortune. But Daley, also like his father, failed to transform the political culture of legalized bribery, the routine funneling of huge city contracts to friends of City Hall--the reality known as "pay to play." Millennium Park may be a source of civic pride and a great tourist attraction, but it was also millions over-budget. Chicago is no less a one-party political city than Beijing; only one of the fifty aldermen is a Republican. And so the impulse to reform these practices is minimal. Stories of corruption, enormous and banal, regularly appear in the Tribune and Sun-Times, but the citizenry kept increasing Daley's margins of victory.

  Sooner or later, any ambitious Chicago politician had to do business with the Mayor and had to think many times before criticizing him. In 2005, in the midst of a series of corruption investigations, which had been described at length in the Sun-Times, Obama told the paper that the articles gave him "huge pause." An hour later, though, he called the paper back and told the reporter that he wanted to clarify his remarks. Daley, he now said, was "obviously going through a rough patch" but the city "never looked better." To talk about endorsing Daley, or not, was "way premature." In January, 2007, Obama endorsed Daley, praising him as "innovative" and "willing to make hard decisions."

  When Obama was not in Springfield or teaching or spending time with his family, he was back to networking. Sometimes that meant making more trips downstate. Sometimes it meant attending the myriad events going on in Chicago: lunches at the business clubs, cultural events, fundraisers on the Lakefront and in the suburbs. After losing so badly to Rush, he started mending fences with black community leaders, clergy, Democratic committeemen, aldermen, and city officials. He attended a regular discussion group at Miller Shakman & Beem, a law firm where Arthur Goldberg and Abner Mikva had practiced. There Obama would talk politics with Abner Mikva, David Axelrod, Newton Minow, Don Rose, Bettylu Saltzman, and various other Democratic activists. Obama wanted to re-establish himself as a Democrat independent of the Daley circle and organization, but also as someone who would not wage an overtly anti-Daley race. He was willing to make common cause with the activists on the South Side as well as with Party regulars like Emil Jones. "This was a guy who was a quick learner," Don Rose said of that period between the congressional and Senate races. "When Obama makes a mistake, he only makes it once."

  The return of the Democrats to power in 2002 also helped Obama in a more subtle way. Like that of many other state senators, his district--the Thirteenth--was reconfigured. In the spring of 2001, anticipating a Democratic sweep, Obama had gone to see a Democratic Party consultant named John Corrigan in a room at the Stratton Office Building, in Springfield, known as the "inner sanctum." The room is locked down; to get in it was necessary to use a fingerprint scanner and tap a code into a keypad. Inside was an array of computer monitors. The Senate Democratic caucus in the legislature had hired Corrigan to look into the details of re-aligning districts in the state to the Party's advantage. This was perfectly legal. The majority party has the right, within legal guidelines, to rearrange legislative borders. The Republicans, of course, preferred to maximize the percentage of African-Americans in a particular district. Because blacks voted almost solely for Democrats, it was better to have one district be close to a hundred-per-cent black and a neighboring district have a minimum number of blacks. The Democrats preferred to spread out their black voters. As Corrigan showed Obama on a computer screen, the best thing that could happen to his district would be to retain the Hyde Park base, along with Englewood and other black neighborhoods, but to push the district north toward the Loop rather than west into poorer black neighborhoods. The district would remain reliably majority African-American and Democratic, but it would also provide more black voters for another district. For Obama, there was an added bonus as he looked forward to a race for the U.S. Senate: his constituency would now include many more wealthy, liberal whites--many of them Jewish--along Lake Michigan. As far as Corrigan could tell, his friend was no longer depressed about the loss to Bobby Rush. He was preparing for the next act.

  "I have seen people who have run for lesser office than Congress and just disappear after losing," Corrigan said. "Barack has always been calm, cool, and collected. Nothing seems to faze him. He doesn't get mad. He is always creative when someone presents a barrier to get through. He can always think or talk his way through things."

  In October, 2002, Obama was touring downstate with Dan Shomon again. One evening, they were standing beside Route 4 in Carlinville, a town of about seven thousand in Macoupin County. The town was known for houses ordered from the Sears catalogue. The two men, who were heading to a political dinner, were discussing what effect a Senate race would have on Obama's family. Shomon knew that Obama was the kind of person who tends to feel guilty, and he thought the race would end up making him feel guilty for the pressures it would put on Michelle. He was already feeling bad that he was missing so much of his little girls' childhood. When they pulled over to the side of the road, Shomon said, "I don't think you should run."

  "I'm running anyway," Obama replied.

  Chapter Ten

  Reconstruction

  In the generation after the Civil War, men of color--some born free, some born into slavery--began to fight their way into statehouses and the halls of Congress. These were, in the main, men of intelligence and bravery: There was Robert Smalls, who stole a Confederate ship in Charleston Harbor and handed it over to Union forces; in Philadelphia, after the war, he caused a sensation when he was thrown off an all-white streetcar and then led a black boycott of the city's transit system. In 1875, Smalls was elected a member of the South Carolina delegation to the House of Representatives. There was Hiram Revels, of Mississippi, a brilliant seminarian and itinerant minister, who had been imprisoned in 1854 in Missouri for preaching to blacks; in 1870, the Mississippi State Senate voted to send him to Washington to serve out the term for a U.S. Senate seat lef
t vacant during the war. Revels, the first African-American in the Senate, served just one year. And there was Blanche Kelso Bruce, a wealthy landowner in Mississippi, who was born to a slave in Virginia. In 1875, he was elected to the U.S. Senate, where he fought for open immigration and the rights of Native Americans; at the 1880 Republican National Convention, Bruce received eight votes for Vice-President.

  For black men and women, however, Reconstruction was a short-lived interregnum between slavery and Jim Crow, between iron subjugation and the rise of insidious voting restrictions and the lynching parties of the Ku Klux Klan. The ability of blacks to run for, and hold, higher office faltered miserably after neo-Confederate insurrection and terror in the mid-eighteen-seventies finally forced Washington to withdraw federal protection of blacks from white violence; by 1900, Southern states began to deny blacks, de facto and de jure, their right to vote. As Eric Foner, the leading historian of Reconstruction, points out, the resistance to black political empowerment was well and cruelly embodied by one of the country's greatest filmmakers and a best-selling historian: D. W. Griffith's "Birth of a Nation" (1915) and Claude Bowers's best-seller The Tragic Era (1929) depicted black office-holders as flamboyantly corrupt mountebanks and helped justify disenfranchisement of black citizens and the brutality of the Klan.

  On January 29, 1901, a black representative from North Carolina, George H. White, stepped forward to give his last speech in the Capitol--and what proved to be the last speech of any black lawmaker in Washington for a generation. White had initiated anti-lynching legislation, but his efforts had come to nothing. The racism that he now faced at home was unbridled. The Raleigh News and Observer expressed parochial shame that "North Carolina should have the only nigger Congressman." The paper's anxieties were soon relieved.

  "This, Mr. Chairman, is perhaps the Negroes' temporary farewell to the American Congress," White told his congressional colleagues, "but let me say, Phoenix-like he will rise up some day and come again. These parting words are in behalf of an outraged, heart-broken, bruised and bleeding, but God-fearing people, faithful, industrious, loyal people, rising people, full of potential force.... The only apology I have for the earnestness with which I have spoken is that I am pleading for the life, the liberty, the future happiness, and manhood suffrage for one-eighth of the entire population of the United States."

  The next time an African-American was elected to Congress was in 1929--this was Oscar De Priest of Chicago. There were no black Southerners in the House until 1973, with the arrival of Barbara Jordan, of Texas, and Andrew Young, of Georgia. The first African-American senators elected in the modern era were Edward Brooke, a Republican from Massachusetts, in 1966, and Carol Moseley Braun, a Democrat from Illinois, in 1992. It was Carol Moseley Braun who was very much on Barack Obama's mind in the fall of 2002.

  Moseley Braun had served only one six-year term in the Senate--a term troubled by allegations of financial impropriety and by an unsanctioned meeting with the Nigerian dictator Sani Abacha. Moseley Braun lost her bid for re-election in 1998 to the wealthy conservative Republican Peter Fitzgerald, who spent fourteen million dollars of his own money on his campaign. When that race was over, she accepted an offer from Bill Clinton to serve as an ambassador--to New Zealand. Fitzgerald's career, it appeared, would be just as brief as Moseley Braun's. After battling for six years with his own state party organization and the Bush White House, Fitzgerald was rumored to be going back to private life and his career as a banker. After losing in 1998, Moseley Braun had said that she would never return to elective politics--"Read my lips. Not. Never. Nein. Nyet."---but she was anything but predictable. Now, in late 2002, Obama was waiting to see if she would attempt to return to the Senate. Operatives in the Democratic Party organization tried to find her a lucrative job offer, but that went nowhere. And Moseley Braun, for her part, cared no more for Obama than, in the end, Alice Palmer did.

  Obama's dilemma was plain: in the 1992 Democratic primary, Moseley Braun won a narrow victory against two white candidates--the incumbent Alan Dixon and a personal-injury lawyer, Albert Hofeld. The way for Obama to win a primary in a crowded field would be to dominate the black and progressive votes in Chicago and the suburbs and to get at least some votes among the more conservative electorate downstate. Moseley Braun's presence in the race would be problematic and probably prohibitive. "Our bases overlapped so much--not just that she was African-American, but that she came out of the progressive wing of the party ... and our donor bases would have been fairly similar," Obama said. "So it would have been difficult, I think, to mobilize the entire coalition that was required for me to run." If Moseley Braun decided to run, he said, "I would probably have stepped out of politics for a while."

  Obama had been traveling the state, alone and with Dan Shomon, from Rockford to Cairo, from East St. Louis to Paris, for many months as an undeclared candidate, but he had not yet sold his closest circle of friends and advisers--much less his wife--on the wisdom of running. Both Valerie Jarrett, who had become a close and trusted friend of the Obamas, and David Axelrod, who was now advising Obama informally, told him that after his loss to Bobby Rush, to lose in a Senate race would finish him in politics. Jarrett and Axelrod felt that Obama would be better off waiting for Richard M. Daley, who had been mayor for more than twelve years, to retire and then run to replace him. He could transform Chicago in a way that Harold Washington hadn't. After all, Obama had been thinking about City Hall since his days as a community organizer.

  Jarrett conspired with Michelle Obama to organize a breakfast at her house and, together with two other friends, the investor John Rogers and the parking-lot magnate Martin Nesbitt, they planned an intervention. Jarrett said that she carefully "stacked the deck" to tell Obama the disappointing news: "We were all against him. We all thought it was a big mistake for his career and that he shouldn't do it.

  "But unlike what he normally does, which is to go around the room and say, 'Tell me what you think,' Barack started out by saying, 'I want to run, and let me explain to you why,'" Jarrett recalled. "We were all kind of taken a little bit aback, because we thought the purpose was to talk about it, not that he'd made a decision. He went through all of his logic. He said, 'I didn't have a big political supporter when I ran for Congress. Now I have Emil Jones. I've already lined him up. I think I can get the necessary aldermanic support. I think it's going to be a crowded field, and that will work to my advantage.'"

  Obama said that he had learned from the mistakes he'd made against Bobby Rush. In that race, he had challenged a powerful black politician with deep roots in a heavily black district--an act of impiety without sufficient justification. Congressional campaigns are waged door-to-door; they are neighborhood battles that often hinge on longstanding name recognition, ethnic solidarity, and personal connections. In a Senate race, Obama's particular talents--his ability to reach out to white suburbanites as well as to blacks and Hispanics; his increasingly evident talent to project on television--would be crucial, especially if he could raise enough money. Obama believed that if Moseley Braun stayed out of the race, he had a chance. According to Jarrett, Obama said, "I told Michelle if I lose, I'm out of politics. That would make her happy." He added, "If what you're worried about is fear, if I'm not afraid to fail, then you shouldn't be afraid to fail. And I need you in order to be successful. So why don't you step up and decide you're going to help me raise some money, because that's the one piece that I don't have worked out."

  By the end of the breakfast, Jarrett had agreed to chair Obama's finance committee. Rogers and Nesbitt agreed to donate both time and money. Nesbitt, in addition to running a parking-lot management company, was a vice-president of the Pritzker Realty Group, a division of the Pritzker empire, one of the biggest fortunes in Chicago. Not long after the breakfast, in the summer of 2002, Nesbitt got the Obama family invited to Penny Pritzker's country house, on Lake Michigan. After talking with the Obamas, Pritzker and her husband, Bryan Traubert, went for a run near their house
and, along the way, decided to play a key role in financing Obama's race. They were soon joined in the campaign by other wealthy Chicagoans: John Bryan, the head of the Sara Lee Corporation, James Crown, and old friends of Obama's like Newton Minow and Abner Mikva.

  Michelle also agreed to go forward, though her anxieties were hardly allayed. "The big issue around the Senate for me was, how on earth can we afford it?" she said. "I don't like to talk about it, because people forget his credit card was maxed out. How are we going to get by? O.K., now we're going to have two households to fund, one here and one in Washington. We have law-school debt, tuition to pay for the children. And we're trying to save for college for the girls.... My thing is, is this just another gamble? It's just killing us. My thing was, this is ridiculous, even if you do win, how are you going to afford this wonderful next step in your life? And he said, 'Well, then, I'm going to write a book, a good book.' And I'm thinking, 'Snake eyes there, buddy. Just write a book, yeah, that's right. Yep, yep, yep. And you'll climb the beanstalk and come back down with the golden egg, Jack.'"

  John Rogers, who had helped Moseley Braun re-establish herself in Chicago after she returned from Auckland, thought that he could sound her out about her plans. "My role was to talk to Carol and determine whether she was going to run and to even nudge her away from it," he said. But Moseley Braun was infuriatingly inscrutable. All Obama could do was continue to make contingency plans, travel around the state speaking at one event after another, and wait.