The Bridge: The Life and Rise of Barack Obama

by David Remnick

  Three months later, on March 19, 2007, both Obama and Clinton were in the race, and Penn wrote another memo that distinguished between the two candidates primarily on the basis of class: "We are the candidate of people with needs. We win women, lower classes, and Democrats (about 3 to 1 in our favor). Obama wins men, upper class, and independents (about 2 to 1 in his favor)." Penn called on Clinton to be the champion of "the invisible Americans" and attempted to establish an iconic distinction between Obama and Clinton: "He may be the J.F.K. in the race, but you are the Bobby." In this dichotomy, J.F.K. represented an entitled, intelligent, elite, cool politician, R.F.K. a man of privilege who had come to identify most closely with the dispossessed--the whites of Appalachia, the Hispanic immigrants of Southern California, Texas, and Florida, the blacks of the inner city. Obama, too, had spoken of the inspiration of R.F.K.'s 1968 Presidential campaign and the coalitions that it had created before his death, but Penn seemed convinced that Hillary Clinton could best summon that romantic, yet tragic, past.

  Penn's memo did not necessarily represent the strategy and psychology of the candidate herself. Clinton's campaign was, in fact, top-heavy with veteran advisers--Harold Ickes, Mandy Grunwald, Howard Wolfson, Patti Solis Doyle--and they generally loathed Penn, seeing him as cynical, pompous, and profoundly mistaken. To them, he was forever the associate of Dick Morris, the centrist operative who left the Clinton circle in disgrace, in 1996, after the tabloids published reports of his involvement with a prostitute. Ickes, who had been an activist in Mississippi during Freedom Summer, Solis Doyle, the daughter of Mexican immigrants, and others counseled greater caution than Penn, particularly on the question of race, and felt that his memos encouraged the candidate to go far beyond the bounds of brass-knuckle campaigning. Penn made no secret of the fact that he was more conservative than the rest of Hillary's team; what he resented was his need to win consensus from advisers who, he felt, were constantly undermining him.

  "It's clear that they resisted a lot of his more sinister suggestions," David Plouffe recalled. Nevertheless, Penn's memo accurately reflected the resentful attitude toward Obama that reporters were noticing in Hillary Clinton's camp both before and during the campaign. Clinton and key advisers felt that Obama was an inexperienced, unschooled upstart, a novice with a talent for public speaking (as long as he was within range of a teleprompter). Obama, they believed, was relying almost solely on his speech-making abilities and the historically glamorous prospect of becoming the first black President.

  In the March 19th memo, Penn suggested that the Clinton campaign target Obama's "lack of American roots." Using that supposed rootlessness, they could cast his candidacy as something fit only for the distant future. "All of these articles about his boyhood in Indonesia and his life in Hawaii are geared towards showing his background is diverse, multicultural and putting that in a new light," he wrote. "Save it for 2050."

  "It also exposes a very strong weakness for him--his roots in basic American values and culture are at best limited," Penn's memo continued. "I cannot imagine America electing a President during a time of war who is not at his center fundamentally American in his thinking and in his values. He told the people of N.H. yesterday he has a Kansas accent because his mother was from there. His mother lived in many states as far as we can tell--but this is an example of the nonsense he uses to cover this up."

  Penn counseled Clinton on how the campaign could "give some life" to these notions "without turning negative":

  Every speech should contain the line you were born in the middle of America to the middle class in the middle of the last century. And talk about the basic bargain as about the deeply American values you grew up with, learned as a child and that drive you today. Values of fairness, compassion, responsibility, giving back.

  Let's explicitly own "American" in our programs, the speeches and the values. He doesn't. Make this a new American Century, the American Strategic Energy fund. Let's use our logo to make some flags we can give out. Let's add flag symbols to the backgrounds.

  We are never going to say anything about his background--we have to show the value of ours when it comes to making decisions, understanding the needs of most Americans--the invisible Americans.

  "The invisible Americans" sounded a great deal like Nixon's "silent majority." Penn's strategy was to cast Obama as the candidate of the elite, a "phony," a neophyte, and an outsider--not quite as American as Hillary Clinton. Long after the race, Penn said to me that the memo "was not in any way, shape, or form meant to have any racial overtones. It was about the notion that [Obama's] childhood in Indonesia somehow better qualified him to manage international affairs--a fact he had repeatedly touted on the campaign trail."

  Within the campaign, there was debate about Penn's tactics and an overall reluctance to highlight Obama's "otherness." But what could be expected of Bill Clinton, who had recovered from quadruple bypass surgery and was planning to campaign? Clinton had grown up in segregated Arkansas, comfortable in his relationships with black men and women. At Yale Law School he often made a point of sitting at the "black table" in the dining hall. Clinton's first adversary as a politician was James (Justice Jim) Johnson, a Klan-supported Democrat turned Republican who ran twice for governor and once for the Senate; Johnson was to the right of Orval Faubus, the infamous segregationist. As President, Clinton defended affirmative action, appointed African-Americans to his Cabinet, awarded Medals of Honor to black veterans whose heroism had been ignored, and apologized for the horrific Tuskegee syphilis experiment conducted on hundreds of black sharecroppers from 1932 to 1972. He delivered a number of speeches admired by the black leadership in Congress and cultivated friendships with leading civil-rights veterans like John Lewis, Andrew Young, and John Hope Franklin.

  And yet Clinton was a politician to the core, a brilliant one, and sometimes a cynical one. Winning came first. During the 1992 campaign, in the midst of the Gennifer Flowers controversy and under attack as a Democrat "soft on crime," he flew to Arkansas and, to bolster his law-and-order bona fides, presided over the execution of a mentally handicapped black prisoner named Ricky Ray Rector, who, eleven years earlier, had killed a police officer. Then, attempting suicide, Rector shot himself in the head, in effect giving himself a lobotomy. The same year, Clinton accepted an invitation to speak at Jesse Jackson's Rainbow Coalition, in Washington, D.C., and then used the occasion to criticize the hip-hop performer Sister Souljah for a foolish comment she had made about black violence. ("If black people kill black people every day, why not have a week and kill white people?") With his host sitting nearby, Clinton compared Sister Souljah to the former Klansman David Duke and criticized Jackson for allowing her to be a member of his organization. It was a performance that infuriated Jackson but appealed to Reagan Democrats--as Clinton undoubtedly intended. "I can maybe work with him, but I know now who he is, what he is," Jackson said of Clinton at the time. "There's nothin' he won't do. He's immune to shame. Move past all the nice posturing and get really down there in him, you find absolutely nothing ... nothing but an appetite." Eventually, Jackson forgave him.

  In 1997, President Clinton initiated a "conversation" on race, led by John Hope Franklin, but it was a pallid, ceremonial affair, which disillusioned some black critics. "The initiative displayed the parochial, shallow self-servingness that besmirches all too much of Clinton's talk about race relations," the Harvard Law School professor Randall Kennedy wrote. "Portrayed as an effort at dialogue, the President's conversation was from the beginning a tightly scripted monologue that regurgitated familiar nostrums while avoiding discussing real problems." Compared with commissions on race under Harry Truman in 1946 and Lyndon Johnson in 1967, Kennedy said, Clinton's effort was "laughable."

  In the long months before the Iowa caucuses and the New Hampshire primary, a generational drama played out among some of the most important figures in the civil-rights generation--a drama that reflected the dilemma of many ordinary African-Americans who were faced with a cho
ice between Hillary Clinton and Obama.

  Some made their choice without hesitation. Vernon Jordan, an attorney who had been president of the National Urban League, and who became a close adviser and friend of the Clintons, had given an early fundraiser for Obama's Senate campaign. But, before Obama announced for the Presidency, Jordan invited him to his house for dinner and told him, "Barack, I am an old Negro who believes that to everything there is a season--and I don't think this is your season.... If you do run, as I think you will, I will be with Hillary. I am too old to trade friendship for race. But, if you win, I will be with you."

  Andrew Young, one of Martin Luther King's close advisers and, later, a mayor, a congressman, and Ambassador to the United Nations, was far less subtle about his loyalties. Speaking on television in December, 2007, Young said that he wanted Obama to be President--but only "in 2016." In a strange ramble for such a serious man, Young warned about Obama's lack of "maturity" and the need for a "protective network."

  "It's like somebody wanting to be the next Martin Luther King," Young said. "They say, I wouldn't wish that on a friend of mine. Martin's home got bombed the first year, they took all his money the second year, and sued him for income-tax evasion. He got stabbed the third year. The fourth year, he came to Atlanta to try to escape from Alabama. They locked him up for picketing ... and put him in a straitjacket, and took him from Atlanta to Reedsville before there were expressways.... Leadership requires suffering, and I would like to see Barack's children get a little older, see, because they're going to pick on them."

  Young even went on about Bill Clinton's racial bona fides as a reason to vote for Hillary. "Bill is every bit as black as Barack," he said. "He's probably gone out with more black women than Barack. I'm clowning, but, when they went to Nelson Mandela's inauguration, they had a whole planeload of black folk who went down there. After the inauguration, there was a party. And Clinton was the one that said, 'Let's start a soul-train line.' All these middle class, bougie folk looked around, 'A soul-train line?' And Bill did the moonwalk in the soul train.... And Hillary pulled her skirt up above her knees, and she got down and went through too.... You look at Barack's campaign, and, first of all, I've talked to people in Chicago, and they don't know anybody around him. To put a brother in there by himself is to set him up for crucifixion."

  Young eventually apologized, but his rhetorical flight did betray some commonly held anxieties about Obama--anxieties not only about his inexperience but also about his safety and about his authenticity as an African-American. Yet again in the life of Barack Obama, there were the old questions: Was he black enough? Was he ready? Was he tough enough?

  Among all the living heroes of civil rights, the figure whom Obama admired most was John Lewis. At first, Lewis had signaled broadly to Obama that he would support him. Even though Obama had come to Washington only in January, 2005, the two men had formed a bond. That year, Obama went to Atlanta to speak at Lewis's sixty-fifth-birthday party.

  Lewis was astonished by Obama's post-Boston appeal. "We walked the streets of Atlanta together and blacks and whites were asking him to run for President," Lewis recalled. "When we got to the restaurant, the waiters and waitresses were asking him to run. And when I introduced him that night I said, 'One day this man will be the President of the United States.'"

  At the Selma speech in March, 2007, Obama felt confident that Lewis would be for him, but through the summer and into the early autumn, the Clintons kept appealing to Lewis on the basis of their long shared history.

  "I've known Bill Clinton for so long--it was more than friendship, it was like a brotherly relationship.... And when Hillary would come to Georgia to speak, she would say, 'When I grow up I want to be like John Lewis,'" Lewis says. Lewis's bond with the Clinton family deepened at their worst moment. In August, 1998, after Bill Clinton went on television to admit to his relationship with Monica Lewinsky--an unprecedented humiliation--Lewis invited him to Union Chapel, on Martha's Vineyard, to commemorate the thirty-fifth anniversary of the March on Washington. "He didn't want to come, but I convinced him," Lewis recalled. "And, when the time came, I got up to introduce him and said, 'Mr. President, I was with you in the beginning and I will be with you in the end.' We both cried.... How could I abandon a friend like that?"

  In October, 2007, Lewis finally came down on the side of the Clintons--there was just too much history to overlook. Lewis is one of the most principled figures in government, but there were also political considerations. Lewis represents the Atlanta area, a majority-black district, and Obama was not yet as well known or as popular as the Clintons among his constituents. "They didn't know him (a), and (b), they thought it was a long shot," Jesse Jackson said. "Black voters are comparatively conservative and practical." In 1984, Jackson had also struggled to get support from African-Americans who didn't think he had a chance.

  For John Lewis, it was an agonizing time. Even before the Iowa caucuses, he was beginning to realize that Obama's candidacy was becoming increasingly serious and that his constituents were shifting away from Clinton. "If I had gone maybe with my gut," he said, "I probably would have gone with Obama from the outset."

  The dilemma was plain. "These were people who knew Bill and Hillary and thought well of them and couldn't quite believe that this young guy with a foreign name had a chance to get elected," the civil-rights activist Julian Bond said. "After two Jackson campaigns, after Al Sharpton's campaign, after Shirley Chisholm, it seemed that these symbolic races hadn't delivered much. The promise had been that these candidates would extract some kind of benefits from the winners and the black cause would be advanced. That turned out to be less true than they had hoped."

  Some civil-rights leaders did side with Obama early. The Reverend Joseph Lowery, a co-founder of the Southern Christian Leadership Conference and a leader of the 1965 march from Selma to Montgomery, told an audience in Atlanta in January, 2007, that "a slave mentality" still haunted those African-Americans who had counseled Obama to wait his turn. He compared those who discouraged Obama to the white ministers who told Martin Luther King, a half century ago, that the time was not ripe for civil dissent. "Martin said the people who were saying 'later' were really saying 'never,'" Lowery said. "The time to do right is always right now." A resident of John Lewis's district, Lowery signed on immediately with the Obama campaign.

  When Lowery heard the news about Lewis's decision, he was just relieved he wasn't a politician. "John wasn't a civil-rights leader anymore, he was a politician, he had relationships and entanglements," Lowery said. "I told the Clintons that if Hillary got the nomination, I would support her, but, in the meantime, I felt Obama was destined to shake up the system."

  Not that every black political or cultural leader was so understanding. The director Spike Lee, whose films include "Do the Right Thing" and a biopic of Malcolm X, was brutally dismissive of those who wavered. "These old black politicians say, 'Ooh, Massuh Clinton was good to us, massuh hired a lot of us, massuh was good!' Hoo!" he said. "Charlie Rangel, David Dinkins--they have to understand this is a new day. People ain't feelin' that stuff. It's like a tide, and the people who get in the way are just gonna get swept out into the ocean."

  Similarly, not everyone in the Obama campaign was quite as forgiving of older black leaders like Lewis as the candidate himself. "Movements are led by the young," the pollster Cornell Belcher said, "and it was comical that the same people who were in their twenties during the civil-rights movement and demanded a seat at the table were now telling Barack Obama it wasn't his time."

  Jesse Jackson, who also sided early with Obama, is an American character of emotional complexity, glaring weaknesses, and, far more than he is ordinarily given credit for, immense importance in the political advance of African-American politicians, including Barack Obama.

  Jackson's flaws--his conceits, his neediness--are so well known that he is readily dismissed by those who do not bother to understand him. George H. W. Bush once called him a "Chicago hustler." Eve
n Martin Luther King, who, in Selma, brought Jackson close, raged against Jackson's need to thrust himself forward. Mario Cuomo, however, may have been right to say that when the definitive history of the 1984 election was finally written, "the longest chapter will be on Jackson."

  "The man didn't have two cents," Cuomo said. "He didn't have one television or radio ad. And look at what he did." What Jackson did was to run the most serious Presidential campaign ever conducted by an African-American--a feat that he repeated in 1988. Even the Chicagoans in Obama's circle who are most dismissive of Jackson admit that he opened the door for them to the White House. Roger Wilkins worked for Jackson in 1984, he said, not because he thought he could win but, rather, to give the country a "civics lesson that there are black people in this country smart enough to be President of the United States."

  Obama might have been wary of Jackson's presence in the campaign, but he could not escape his influence. In 2007 and 2008, when Obama quoted from King's speeches--quoted them with the same sense of reverence as a jazz musician quoting a passage in Armstrong or Coltrane--this was something fresh and affecting for younger voters. But it was hardly new. "When you are unkind to the homeless, disparaging them as derelicts, you on treacherous moral ground, Mr. Bush," Jackson said in the 1988 campaign. "'cause there is another power. 'The moral arc of the universe is long, but it bends toward justice.' Those who cannot defend themselves, they got a silent partner, they got ... got another power. And when you, when you attack liberals, good-hearted folks, lovers of civil liberties, Mr. Bush--Mr. Bush, watch out! You tamperin' with another power!" Jackson had a distinctively different style from Obama, but the sources of their inspiration converged.

  Jackson did not intend merely to quote the prophetic voice of King for political purposes; he spoke in that voice because it was his own. Jackson pushed issues that were not always permissible in mainstream politics in 1984 and 1988, including Palestinian rights and opposition to South African apartheid. He received so many death threats that he often wore a bulletproof vest when he gave a speech.