The Legend of Barack Obama

From out of nowhere, he’s become DC’s brightest star. Will his charisma and sense of destiny propel him to the White House in 2008?

By: Garrett M. Graff

Obama, half black and half white, has always lived in both worlds. Photo by Garrett Graff.

From the November 2006 issue of Washingtonian  

Iowa senator Tom Harkin stood at the podium firing up the 3,000 supporters who had paid $25 to join him at the Warren County Fairgrounds in September. The scene was the annual Harkin Steak Fry, a gathering of Hawkeye State Democrats that, with Iowa’s vital spot in the presidential elections, is always a larger stage than the pumpkin-and-hay-bale-bedecked platform it takes place on. It was Harkin’s 29th such gathering, but the day belonged to a 45-year-old freshman senator from Illinois—or as Harkin called him, “the kid next door.”

“Honestly—tell you the truth—I really tried to get Bono this weekend,” Harkin told the crowd. “I settled for the second biggest rock star in America.”

The crowd came to its feet cheering as a smiling Barack Obama rose. “What a warm reception,” Obama began. “I’m going to have to come to Iowa again.” Obama didn’t wink, but his meaning was clear. The crowd went wild.

A few short years ago, no one had heard of the skinny Chicago state senator and constitutional-law professor with the big ears and the funny name. A few months ago, he would have gamely demurred when asked if he’d run for president in 2008. Now all bets are off. According to advisers, colleagues, and friends, Obama just might be willing to be the next president of the United States. It would be the capstone of an amazing rise for a politician whose charisma and personal story—half-Ken­yan, half-Kansan, a Hawaii-born, Harvard-educated lawyer—has breathed life into the Democratic Party.

At the heart of “Obamania” is his personality and presence—part preacher, part professor, part movie star. His charisma seems effortless, his charm an afterthought. National Journal White House reporter Alexis Simendinger recalls the first time Obama visited the White House after his election. He was mingling in the East Room with other members of Congress. As she watched him move through the crowd, a photographer asked, “Who is that guy? He’s certainly got ‘It.’ ”

The question now is how far “it” takes Obama—and how fast.

During his two years on the national stage, Obama has collected a lifetime’s worth of honors and accolades: Just months after winning the Democratic primary for the US Senate—and before he became only the third African-American since Reconstruction to serve in that body—he delivered the keynote address at the 2004 national convention. He won a Grammy for the audio version of his memoir, which spent a year on the New York Times bestseller list. He posed for photographer Annie Leibowitz for the cover of Men’s Vogue. He’s been on the cover of Newsweek. On Will & Grace, Grace said she dreamed she was in the shower with Obama and that he was “Ba-rocking my world.”

In terms of seniority, Obama is the 98th senator in the 100-member club; he moved up from 99th when Jon Corzine left to be governor of New Jersey. At home in Illinois he jokes that being 98th means his only task is sharpening pencils. But he’s third-to-last in rank only.

Obama suddenly has found himself the standard-bearer for a generation. He need look no farther than his desk in the Senate chamber to be reminded of the last politician who embodied the hopes of a generation: The inside is signed by its previous occupants, including Bobby Kennedy.

Much of Obama’s allure is that he is new and exciting enough to be a sort of blank canvas onto which activists of all kinds can paint their aspirations. Says Chris Lu, his legislative director, “He’s like a Rorschach test—you see in him what you want.”

Where he goes from here, what he does with his popularity and fame, is a guessing game. With his new book, The Audacity of Hope —a meditation on American values—out in October, Obama launches a book tour and continues a soul-searching process that will determine whether he runs for president in 2008. All signs point to yes.

Obama’s 2004 keynote address at the Democratic convention, delivered in his sonorous baritone voice, transformed him into a rock star—or at least the hottest thing in the Democratic Party. By the time he arrived in Washington as a freshman senator he was much bigger than his transitional office in the basement of the Dirksen Senate Office Building. “He leapfrogged Washington before he got there,” says longtime aide Dan Shomon.

Since the day he arrived—the first question at his first press conference was “Senator Obama, what is your place in history?”—the only matter of debate in Democratic circles was not if he would run for president but when: Would he take a shot in 2008 or wait until 2012?

As hard as Obama has worked in his career, luck has played a big role in his rise. The frontrunner in his 2004 Senate primary, Blair Hull, and his Republican opponent, Jack Ryan, both were tripped up by troubles with their ex-wives. Had it not been for a restraining order against Hull and allegations of Ryan’s trips to sex clubs, Obama might never have stood before the Democrats in Boston that July. “He knows that he may be the best politician in America, but he also knows that in 2004 he was one of the luckiest,” says David Axelrod, his top political adviser.

A combination of skill and luck put Obama where he is today: poised to be the first black US president—if he wants to be. There are hurdles he has to clear. He has no administrative or executive experience. And although he has dedicated himself to foreign policy, he has no national-security background.

Then there’s his family: His wife, Michelle, has opposed his forays into electoral politics because of the strain it puts on the family and the long absences it requires from their daughters, Sasha, five, and Malia, eight. According to sources close to the family, she has expressed concerns about his security should he seek the presidency. “It’s a good time for his politics, but it’s not a good time for him personally, with his young family,” says adviser and law-school classmate Cassandra Butts.

At least half a dozen African-Americans have preceded Obama as candidates to be America’s first black president, from Jesse Jackson to Virginia’s Douglas Wilder. Colin Powell’s 1995 flirtation with the race traced much the same arc Obama’s has—the “Draft Powell” movement coincided with the publication of his memoir. But none has arrived at what seems to be such an opportune time with such broad appeal.

Poised for a multicity book tour and an appearance on Oprah, Obama is into a fall full of speculation.

Obama is cutting a new path in modern politics—one in which he is his own trailblazer. His campaigns for state senator and the US Senate were successful without early support from the Democratic Party. By the time the Democrats threw their arms around him in 2004, Obama was well on his way. “If you think about his trajectory, it was pretty much just Barack on his own. He’s been his own best political adviser for quite some time,” says Butts.

Intensely competitive, Obama typically saves his fiercest battles for the Scrabble board, the basketball court, or the golf course. He has navigated his political career in a way that has created few real enemies. “If Barack has any enemies out there, they come from just sheer jealously,” says Illinois state senator Kirk Dillard, a Republican. “I don’t believe he has any enemies who have a good reason.”

In Washington, Obama has become a policy wonk. “He’s an amazing person in his capacity to understand the issues,” says Chris Lu. Obama also has worked to develop the framework for his worldview and approach to governing. “Early on he wanted to come up with an overarching narrative,” says Samantha Power, who worked with him on foreign policy. “I was really struck by that desire to front-load the big thinking, the toughness of cracking this nut, articulating this balance between freedom and security.”

Obama has been frustrated by what he sees as the Senate’s wasted opportunities. “I think what has frustrated him more than the process itself is how the Republicans aren’t interested in the issues that he thinks are important to the American people,” says Lu, who explains that Obama would rather concentrate on issues facing the middle class, like healthcare and education, instead of the ideological issues the Republicans have been pushing. Says Obama, “A lot of times what gets done in Washington on a day-to-day basis isn’t all that much.”

The senator’s highest-profile ventures have been bipartisan, including a tutelage in nuclear nonproliferation with Indiana’s Richard Lugar that took Obama to Eastern Europe and Russia, an effort to bring transparency to government contracting with Oklahoma senator Tom Coburn, and a push for immigration reform with Florida’s Mel Martinez. Obama was the first to raise the threat of avian flu on the Senate floor and has spoken out for victims of Hurricane Katrina, pushed for alternative-energy development, and championed improved veterans’ benefits—all while working to expand his support in Illinois, where he held 39 town-hall meetings in his first year. “You have to devote time—things don’t just happen here because of who he is,” Butts says.

Every Thursday, Obama and his Illinois colleague Dick Durbin host a constituent breakfast at the Capitol, a tradition of bagels, coffee, and policy talk that began with Senator Paul Simon in 1985. With Obama, attendance has swelled to the point that people have to be turned away. While decrying recent corruption scandals, he decided to practice what he preached: After taking 23 subsidized rides on corporate jets last year, Obama said he will have his campaign reimburse in full those companies whose planes he rides on.

As a member of the Foreign Relations committee, Obama is moving onto the world stage. An August trip to Africa found him visiting the cell where Nelson Mandela was held, talking terrorism in Djibouti, taking an AIDS test in Kenya, and visiting the rural village where his grandmother still lives. It covered the gamut of foreign-policy and national-security issues. The trip, half educational and half celebratory, had been in the works almost since the day Obama was elected to the Senate; he’s planning another to Southeast Asia and Indonesia, where he spent several years growing up while his mother worked at a US embassy. The Obama on display in Africa was more than a senator on a junket—it was Obama as beacon of American hope and optimism.

In South Africa, Archbishop Desmond Tutu teased the senator: “You are going to be a very credible presidential candidate.” According to the Chicago Sun-Times’s Lynn Sweet, Obama flinched and replied, “Oh, no, don’t do that.”

Though humble in the face of all the attention, Obama uses it to his advantage. One of the Democrats’ top fundraising draws, Obama has campaigned across the country, amassing IOUs from elected officials at every level. He’s raised money for dozens of candidates, all the while helping build the star power of the Democratic Party. “He does have a lot of credits in the bank, and when the time is right . . . he’ll definitely cash them in,” says Chicago congresswoman Jan Schakowsky.

For the moment Obama laughs off talk about 2008, but the staff he’s recruited exceeds the needs of a freshman senator. His Internet director, Jim Brayton, ran much of the online operations for Howard Dean’s 2004 presidential campaign, and Obama tapped as his foreign-policy adviser Samantha Power, a Pulitzer Prize–winning Harvard expert on human rights. His chief of staff, Pete Rouse, served in that role for former Senate majority leader Tom Daschle, and communications director Robert Gibbs is a veteran of John Kerry’s presidential campaign.

Few observers failed to notice that at Obama’s shoulder during the Harkin Steak Fry was Steve Hildebrand, who managed the Iowa caucuses for the victorious Kerry in 2004. Staff members deny that they were hired for an eventual presidential bid, but it’s clear that Obama can call upon top talent should he run.

Part of what sets Obama apart in the Senate is his relative youth. One of the first senators born in the 1960s, in a chamber dominated by greatest-generation colleagues, Obama is more likely to find peers on his staff—like legislative director and law-school classmate Chris Lu—than on the Senate floor. He has cordial but not close relations with party elders like Ted Kennedy. Advisers say Obama isn’t always comfortable with the party’s talking points; he prefers to discuss issues in his own words, reframing topics as he goes. His political adviser, consultant David Axelrod, is still based in Chicago. Obama travels with only a few aides—he is, he says, “a solo act.”

Obama’s decision to have his family stay in Chicago, close to his wife’s family, has shaped his approach to Washington. He rarely lingers in the capital, returning to Chicago whenever possible, even for as little as 24 hours at a time. He rarely attends evening social events. He prefers working dinners at places like Charlie Palmer Steak on the Hill; these can stretch for hours as he debates issues and picks the brains of people he assembles for a meal. He works out regularly in the Senate gym or at a club close to his one-bedroom apartment on Massachusetts Avenue near Chinatown.

Friends describe Obama’s wife, Michelle—a lawyer he met in 1988 when they worked briefly at the same Chicago firm—as his rock. Obama jokes that she is one of the two “higher powers” he consults with regularly.

Friends say one of the most striking changes from his old Chicago days is his attire:

He’s gone from wearing tattered sweaters and looking like a graduate student, even as a constitutional-law professor at the University of Chicago, to dressing in sharp suits from Barneys. Part of the difference is money: This year his reissued 1995 memoir brought in hundreds of thousands of dollars; the $1.9-million advance he got for his new three-book deal allowed him to pay off 15-year-old student loans and move his family out of an apartment and into a new $1.6-million house in Chicago’s Hyde Park neighborhood.

The financial security has boosted Obama’s already considerable confidence. Advisers say he’s more relaxed now that, for the first time in his life, he doesn’t have to worry about paying next month’s rent.

“One of the questions that Michelle kept asking when I was planning to run for the Senate was how are we going to manage all this?” Obama says. “I explained that what’s going to happen is, I’m going to win the primary, win the general, and then I’m going to write a book.” He laughs and fast-forwards to his arrival in Washington. “At the Mandarin hotel for orientation, we got off the elevator, I’d gotten my book contract, and she looked at me and said, ‘I can’t believe you pulled this off.’ ”

Obama’s biggest accomplishments as a freshman senator have taken place outside the Capitol. His “Call to Renewal” speech at DC’s National City Christian Church this past summer was perhaps the most important dissection of the political world and the role of faith made by any Democratic politician in a generation. Faith, he argued, was an important part of the American reform tradition—and yet Americans must remember that it was the most religious Founders who insisted on the separation of church and state so people could not be persecuted for their beliefs. More broadly, he has inspired in a generation of political activists a measure of hope for a better, more united America.

Obama’s broad appeal was evident in the thousands who turned out to see him in Iowa in September. College student Veronica Czastkiewicz, 19, drove three hours to hear Obama speak at the steak fry even though she’s a Republican. “Barack’s attitude is awesome. If he runs, I’d love to vote for him over any of the other names I’ve heard,” she said. “Barack’s the only Democrat I’d vote for.”

In his Call to Renewal speech Obama said Americans are seeking guidance in the uncertainty of modern life, and for politics to ignore, or worse, demean that search for meaning is a disservice to the nation. “They want a sense of purpose, a narrative arc to their lives,” he said. “They need an assurance that somebody out there cares about them, is listening to them—that they are not just destined to travel down the long highway towards nothingness.”

He was talking about Americans, but he might have been talking about himself.

Obama’s unusual family history is cited frequently as an embodiment of the American dream. His mother’s parents went to school on the GI Bill and bought a house in Kansas with an FHA loan. His father grew up herding goats in a Kenyan village before attending the University of Hawaii and Harvard. Obama was born in Hawaii, and his father, also named Barack, left when his son was two to return to Kenya. At age six Obama and his younger sister, Maya, moved to Indonesia with their mother when she remarried. After four years in the Pacific-island nation, Obama returned to Honolulu to live with his mother’s parents. His father died in a car accident in Kenya when Obama was 21.

In his memoir, Dreams From My Father, Obama writes about his struggles over his absent father, his white mother, his mixed-race heritage, and his faith and how he fell “into exaggerated stereotypes of black male behavior.” He tried marijuana and cocaine; he didn’t use heroin because he didn’t like the dealer who tried to sell it to him. In time he straightened himself out, heading to the mainland for Occidental College in California. He then transferred to Columbia University; in New York City he was surprised by the racial tension he encountered. He moved to Chicago in 1985 to work as a community organizer for a church-based group on the South Side.

Obama’s confidence stems in part from his education—from his days at Punahou, Hawaii’s elite prep school, to Occidental to Columbia to Harvard Law School, where he was the first black editor of the law review. “The kind of education I received makes you confident in your ability to understand problems—not necessarily to have good answers but at least understand the nature of the questions,” he says.

Harvard law professor Laurence Tribe, one of the nation’s leading constitutional scholars, calls Obama “one of the two most talented students I’ve had in 37 years in teaching. . . . When I look at my kids and grandkids and ask what makes me hopeful about the future—one thing is Barack Obama.”

After law school, Obama shunned clerkships and high-powered law-firm jobs to return to Chicago, where he organized a big voter-registration drive and got involved in politics, running for a state-senate seat at the urging of colleagues—and winning—in 1996.

He was greeted in the capital, Springfield, by much the same situation he would find in 2005 in Washington: The Senate Democrats were a minority in a state controlled by a Republican governor. Emil Jones, now the president of the senate and then the minority leader, recalls that Obama came to him and said, “I want to work.”

“That’s very rare,” Jones says. “He’s always someone who has wanted to work and champion causes. He’s always been that way.”

“When he first came to Springfield, many resented his good looks, his articulate speaking ability, and his intellect,” recalls state senator Kirk Dillard, a Republican. But Obama’s desire to move issues forward won over Dillard and many of his colleagues. “He’ll show up at any meeting that requires his attention,” Dillard says.

In Springfield, Obama made friends and built coalitions with the help of a weekly bipartisan poker game. He championed ethics reform and reform of the state’s death-penalty process. When Democrats became the majority, he chaired the health committee, but his best-known accomplishment was a requirement that police videotape interrogations in capital cases.

“It’s remarkable that a reform-minded newcomer could get as much accomplished as he did,” recalls federal judge Abner Mikva, who had tried to recruit Obama to clerk for him after law school. “He made a lot of friends.”

By 2000, after four years in the state senate, Obama was impatient. He was teaching constitutional law at the University of Chicago and working in the legislature. In an ill-advised run against Democratic congressman Bobby Rush in 2000, Obama was beaten 2-to-1 in the primary, leaving him almost broke and prompting a Chicago political reporter to ask on the air, “Is Obama dead?” The campaign was, according to his advisers, a valuable political lesson.

By 2004, Obama had mastered the game. He got out of the gate early, declaring in January 2003 that he was going to seek the US Senate seat. He’d already become a local leader against the Iraq war. At a rally at Chicago’s Federal Plaza in 2002, long before anyone had heard of him nationally, he delivered an eloquent speech warning of the dangers of the war ahead. Just as Abraham Lincoln’s antislavery speech at New York’s Cooper Union in 1860 launched his national career, Obama’s Federal Plaza speech might be seen as his launching pad.

The Senate race turned into a walk as his opponents imploded and he won the seven-person primary with 53 percent of the vote, polling well even in the “collar” counties around Chicago that were assumed never to support a black candidate. Following his 2004 convention keynote speech, he was so far ahead of his opponent, the imported Maryland bombaster Alan Keyes, that Obama spent much of the fall campaigning around the country for other candidates.

“Obama now carries a burden of expectations and pressures that few political leaders could ever satisfactorily meet,” the Chicago Tribune wrote on the eve of the election. After two years in the Senate, his star is even brighter, he’s even more popular across the country, and his exposure in the coming months may be all he needs to get into the 2008 presidential race.

Few around him believe it’s in his best interest to stay in the Senate. The only two US senators to win the presidency in the last century—Warren Harding and John F. Kennedy—did so in their first terms. Numerous senators have failed in their presidential bids, most recently John Kerry and John Edwards.

Says colleague Dick Durbin, “I said to him a while back, ‘You think that casting about here for four more years and casting 2,000 more votes will help you be a better president?’ ”

“Barack’s in a category of his own right now,” says Congresswoman Schakowsky. “This is a phenomenon I don’t think we’ve ever seen before. I think 2008 is just the right time.”

“Everything is timing in this business, and ’08 is on him,” says his Illinois political godfather, Emil Jones. “If he doesn’t go in ’08, it may not come around again.”

The looming presidential race is as wide open an election as has been seen in modern politics. “What we saw in ’04 was don’t miss out on an opportunity with an open seat,” says Dan Shomon. “Barack would not be able to live with himself 20 years down the road if he looked back and realized he blew his chance. He wants to be the number one guy. He’s not going to wait 20 years to do that.”

“If I had to guess right now, I’d say he’s going to run.”

The walls of Obama’s office in the Hart building are decorated with photos of Nelson Mandela, Abraham Lincoln, Martin Luther King Jr., John F. Kennedy, Mahatma Gandhi, Thurgood Marshall, and Muhammad Ali—historical figures Obama cites as his role models in public service.

Lincoln, that other favorite son of Illinois, is a central part of Obama’s world. When he goes out running, he occasionally ends up at the Lincoln Memorial, standing on the steps, looking out from where King delivered his “I Have a Dream” speech. Obama is introspective, churning over issues in his mind during long, contemplative walks. As is evident from his 1995 memoir, he spends time internally debating his identity, his faith, his calling in the world, his God.

“I’ve had to reconcile a lot of different forces in my life,” Obama says. “For me growing up, nothing was given.” He says some of the introspection comes from his days teaching constitutional law, when he had to examine all sides of an argument and fairly present the evidence.

He came to his faith in God in adulthood, and it is a central facet of his life; his pastor in Chicago, Jeremiah Wright at the Trinity United Church of Christ, provided the phrase that is the title of his new book, The Audacity of Hope.

The book is meant, Obama says, to reinject meaning into American civic life. It is trademark Obama—written in his almost singsong style during long nights over the spring and summer. In it is the voice of a man who is frustrated with the pace of the Senate, frustrated with petty politics. Read between the lines, it is the book of someone with bigger plans and bigger ideas.

In the end, Obama might be pushed toward the presidency by what he calls his restlessness. At every stage of his life, he’s reached for the next rung.

“The more successful Senator Obama has become, the more impatient he’s become,” says Kirk Dillard, “because he knows how much more he can accomplish.”

Obama has long said he’s not running for president in 2008, but recently he’s been leaving the door open a crack. Things change, he’ll say when pressed. And there was that trip to Iowa, where he was besieged by media and fans. If he doesn’t run, he’d be a top contender for a vice-presidential nod, although his advisers say he’d be unlikely to take it. Obama’s star is bigger and brighter than most of his fellow Democrats’—why would he settle for number two?

He keeps counsel with a small group of advisers and law-school classmates like Butts. But he says flatly that he’s his own best adviser. “He’s not a guy who’s looking to people to tell him what to do. He knows who he is and what he wants to do,” says Axelrod, who is in daily contact with Obama and his staff.

“I have good instincts about big-picture politics. I’m not a political mechanic,” Obama says. “There are a lot of people who are a lot smarter when it comes to press turnout, polling, or what have you. . . . But in terms of what’s important to the country and what’s important to people, I think my instincts are good. I trust them.”

A question facing Obama is whether he’s ready for the pace of the campaign trail, the weeks away from his family. “The decision to run for President of the United States is a much different decision than to run for any other office,” says Axelrod. “It’s not something that you should take lightly. It’s not the next move on a chessboard.” Reach too soon and you may never get another chance. Reach too late and you might miss your moment.

History is littered with people like Obama. Cyril Connolly, who was widely believed to be the greatest English writer of his generation, failed to deliver a single noteworthy work of literature. In his autobiography, The Enemies of Promise, Connolly tried to explain his shortcomings: “Whom the gods wish to destroy they first call promising.”

In today’s political world, no one is more promising than Obama. While he gamely handles most of the attention, there are cracks. His smoking habit—three Marlboros a day, never around his family—which he tries regularly to stop, restarted during the 2004 race, and he’s still struggling with it.

The immediate hurdle is that he hasn’t built any infrastructure for a presidential run—and despite a summer meeting with major donors to his Hopefund PAC, he hasn’t begun raising money. According to Axelrod, Obama hasn’t done any polling since his 2004 election. But he probably could ramp up an effort quickly if he decides that 2008 is his moment. “He’s the only one who could flip a switch, raise money, and hire talent,” says Jeff Zeleny, who covered Obama for the Chicago Tribune.

If he ran, Obama would run smack into his colleague Hillary Rodham Clinton. In becoming the Democrats’ other celebrity senator, Obama has tried to follow the so-called “Clinton model”—to be seen as a “workhorse” rather than a “show horse.” The two superstars—Obama and Clinton—as well as their Republican counterpart, John McCain, operate on a different stage than the other 97 senators.

In key ways, Clinton and Obama are opposites. Clinton is a pragmatist who takes the existing framework and figures out what she can accomplish in the “real world.” She tends to focus on policy bit by bit rather than reaching for a larger message. Obama, says Lu, his legislative director, is a dreamer more likely to ask, “Why accept the way it is as the way it is?”

Says Obama: “The way I approach problems is to say, ‘What’s the optimal solution?’ and then work backwards. I like to start with the idea—what’s true to me? Or what’s the best approximation of true?”

Hillary Clinton can’t match Obama’s rhetorical skills and often doesn’t come across well in larger groups. She wins over smaller groups and individuals one-on-one. Obama is the master of the large group. “I’ve seen him get going, and he just hits it. He feeds off the crowd,” says Shomon. In smaller groups, he says, Obama “gets sleepy, and he can make you sleepy.”

Obama isn’t a backslapper and gladhander like Bill Clinton. His demeanor is almost preternaturally calm—his poise makes him seem instantly in command. He’ll sign your book, take a photo with you, or give an autograph, but it’s done with a bit of bemusement at his own fame.

And where Bill Clinton’s rise was marked at every turn by scandal, controversy, and partisan vitriol, Obama has sailed through his brief time on the national stage largely free of controversy, burnishing his image as the hope of a new generation.

His September speech in Iowa, while long on traditional Democratic themes, had that extra something the crowd yearned for—the “it” factor. Strip away his charisma, strip away his personal story, and lots of candidates could have given a similar speech—but Obama is different.

In the end, Obama will probably make the decision on whether to run in 2008 during a long walk down the Mall or while staring at the icons on his office wall.

“I agree with the saying that timing is everything, but I believe that whether you have a good sense of timing is largely determined retrospectively,” he says. “I am a believer in Woody Allen’s adage that 80 percent of success is showing up.

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