Is he tough enough? That’s the question being asked of Barack Obama. To those who have known the candidate since boyhood, it’s not just those “dreams from my father” that make Obama a contender, but also his mother’s daring, his grandmother’s grit, and his own relentless drive.
Senator Barack Obama (with Lincoln and King) in his Capitol Hill office. Photograph by Jonas Karlsson. View images of the young Barack Obama.
By the fall of 2002, Barack Obama had been in the Illinois state senate for not quite six years. He was a member of the Democratic minority, representing a swath of Chicago’s South Side. He had done what he could in a state capital where Republicans ruled, and he was ready for a change. As it happened, so were voters in Illinois, who that November put the Democrats back in power in Springfield.
A few months later Obama went to see Emil Jones Jr., the newly chosen state-senate president and the man who loomed as perhaps the most powerful black politician in Illinois. He went to see Jones with a big idea. By that point the two men had known each other for the better part of 20 years, but theirs had not always been an easy relationship. They had first met in the mid-1980s, when Obama, as a community organizer on the far South Side, had seen Jones as an “old ward heeler” who backed the wrong horse in Harold Washington’s successful quest to become the city’s first black mayor. Jones had had to jockey for a place on the stage near the new mayor at a public event that Obama had helped plan.
Jones, a chain-smoking, gravelly voiced, unvarnished throwback to the era of the old Daley machine, was wary of Obama, a freshly minted agitator from Columbia University. Obama and other community activists were the sort who used politicians as foils, “shunned them, more or less, I guess,” Jones told me on a winter morning, a cigarette smoldering in the ashtray in his office high above the city that Carl Sandburg famously called “coarse and strong and cunning.” Jones went on: “They were in-your-face types. I happened to see them out there one day. And I told them, I said, ‘You don’t gotta be outside. Come on in the office.’ ”
A friendship was born. A decade later, after returning to Chicago with a law degree and the mantle of first black president of the Harvard Law Review, Obama won his own state-senate seat, taking the place of an incumbent who had decided to run for Congress, placed a distant third in the Democratic primary, changed her mind, and—with Jones’s help—tried to run for her old seat after all. Obama’s team, in a move as bold as it was adroit, challenged her nominating petitions and managed to keep her name off the ballot. Obama arrived in Springfield and told Jones, then the minority leader, that he wanted to “work hard.” He promptly became Jones’s point person on a number of tricky issues, including ethics reform. Now, with Jones elevated to the senate presidency, Obama was approaching him with a cold-eyed proposal.
“After I was elected president, in 2003, he came to see me, a couple months later,” Jones recalled, relishing the tale. “And he said to me, he said, ‘You’re the senate president now, and with that, you have a lot of pow-er.’ ” Jones stretched out the word, as if savoring the pleasure of it, and his voice became very quiet as he continued: “And I told Barack, ‘You think I got a lot of pow-er now?,’ and he said, ‘Yeah, you got a lot of pow-er.’ And I said, ‘What kind of pow-er do I have?’ He said, ‘You have the pow-er to make a United States sen-a-tor!’ ” Jones let out a soft, smoky laugh. “I said to Barack, I said, ‘That sounds good!’ I said, ‘I haven’t even thought of that.’ I said, ‘Do you have someone in mind you think I could make?,’ and he said, ‘Yeah. Me.’ ”
Jones let the words hang for a moment, and then went on. “The most interesting conversation. And so I said to him, ‘Let me think about this.’ ” Obama knew that Jones’s support could single-handedly freeze the discretion of other powerful politicians in the state, and put endorsements of possible rivals on ice. “We met a little later that day, and I said, ‘That sounds good. Let’s go for it.’ ”
This is not a story about the presidential horse race. It’s not about the policy positions of a freshman senator and candidate for national office. It’s about the enduring character of a boy and a young man, and how that character has emerged in adulthood. The Barack Obama who wrote so poignantly of adolescent alienation and the search for racial identity is the same Barack Obama who learned, the hard way, how to deal with the likes of Emil Jones Jr., a man whose cell-phone ring tone is the theme from The Godfather. Obama’s good looks and soft-spoken willingness to ponder aloud some of the inanities of modern politics have masked the hard inner core and unyielding ambition that have long burned beneath the surface shimmer. He is not, and never has been, soft. He’s not laid-back. He’s not an accidental man. His friends and family may be surprised by the rapidity of his rise, but they’re not surprised by the fact of it.
In The Audacity of Hope, whose publication in the fall of 2006 effectively turned what was first billed as a book tour into a march toward the New Hampshire primary, Obama cops a plea to the quintessential qualification for any presidential candidate: “a chronic restlessness, an inability to appreciate, no matter how well things were going, those blessings that were right there in front of me.” He has tried to turn this to his advantage. “I know I haven’t spent a lot of time learning the ways of Washington,” he said in announcing that he would run for president. “But I’ve been there long enough to know that the ways of Washington must change.” Obama’s restlessness is a quality that would lead him to conclude, again and again, that the time had come to make a move—to take a chance, to aim higher—when others told him to wait his turn. Far more often than not, his timing has been right.
As the presidential campaign whirls through the front-loaded primary season, Obama’s character has been under high magnification. The main point of attack is that he is not “tough enough” or experienced enough; New York Times columnist Maureen Dowd titled a column about him “The 46-Year-Old Virgin.” Hillary Clinton has openly encouraged this derisive assessment for many months. At the same time, coming across as too tough and gritty—too skilled at the sharp-elbowed arts of politics—will undermine the very qualities that make Obama attractive in the first place. The trap is obvious.
The rare talent is to wear ambition lightly, and to allow toughness to be taken for granted. Obama’s life and career suggest he has that talent—or at least that gift. He long ago decided that he had a chance to make something extraordinary of himself. With a calculating consistency that may not always have been apparent to others, or even sometimes to himself, he set out to do just that. His half-sister, Maya Soetoro-Ng, a schoolteacher in Hawaii, says simply, “He’s a very cool customer.”
Wags More, Barks Less
“This campaign cannot be about me,” Obama told a cheering crowd in Chicago on the weekend he declared his candidacy, a year ago. “I am an imperfect vessel for your hopes and dreams.” But, for better or worse, his own campaign is all about him and the compelling idea he embodies.
His life is the story of a person just slightly ahead of his time, of a boy and a man whose search for the meaning of his paternity, and thus his identity, has led him, over and over again, to make his own luck. Every person alive faces the challenge of finding a place in the world. Obama had to work harder than most to find his own place, and he long ago concluded that it would be a prominent one, in the public arena.
Barack Hussein Obama owes his very existence to a defiance of conventional odds. He was born and came of age in Hawaii, the 50th state and in many ways among the freest-thinking, where mixed-race ancestry is such a given that residents refer to their own backgrounds as “chop suey” or “poi dog,” where hotel-room bureau drawers hold not only the Gideon Bible but the Book of Mormon and the Teachings of the Buddha, and where bumper stickers urge, wag more, bark less. If Obama comes across as a bit of a softy—if you don’t see the toughness or the ambition at first—it may be in part because he spent his formative years in a place where “Live Aloha” had not yet become a slogan aimed at recapturing a more gracious time, but was simply a way of life.
His mother, Stanley Ann Dunham, was the white daughter of a Kansas furniture and insurance salesman who had wanted a son, and who moved to Hawaii on the eve of statehood in search of a new lease on life. She loved the speeches of Martin Luther King Jr. and the music of Mahalia Jackson, and thought Harry Belafonte was, as her son remembers, “the best-looking man on the planet.” At 18, she met and married Barack Hussein Obama Sr., a former Kenyan goatherd and an economist-in-training who had recently become the first African student in the history of the University of Hawaii—this in 1960, a time when inter-racial marriage was still illegal in almost half the mainland states. The couple divorced in 1963, when their son was just 2, and Barack met his father (who ultimately claimed paternity of a total of eight children by four women before dying in a car crash at age 52, in 1983) precisely once more in his life—for a month, at Christmas, in Honolulu, when he was 10.
Two-year-old Barack Hussein Obama in Honolulu, Hawaii, in 1963. From Polaris.
View images of the young Barack Obama.
Ann next married an Indonesian national named Lolo Soetoro. She eventually began pursuing a Ph.D. in anthropology that required frequent fieldwork in Indonesia, and Barack spent four years of his childhood there, in the world’s most populous Muslim nation. Because his mother wanted Barack to have the best possible bite at the American Dream, she left him in Hawaii for much of his adolescence in the care of his maternal grandparents, Stanley and Madelyn Dunham, who fed him a poly-cultural diet of sashimi and Jell-O with grapes, and got him admission and a scholarship to the prestigious Punahou School, in Honolulu. He arrived there in fifth grade as a round-faced boy with baby fat, and left the lanky figure of today.
Yet Obama had to grapple with the reality of life as one of only three black students in an elite high school of 1,200. The yearbooks show him as a respectable contributor but not a star. A friend once scrawled his funny-sounding last name in wet concrete outside the cafeteria, as a goof that might get him into mild trouble. (School officials point it out proudly these days, the way presidents point out the holes from Ike’s golf spikes in the Oval Office floor.) By diligent effort, constant practice, and a mean jump shot, he made the second string of the state-champion basketball team in his senior year, earning a slot that might have gone to a younger, more promising player. He went to college for two years in the West Coast sprawl of Los Angeles—at Occidental—and for two years in the dominant East Coast metropolis of New York, where he transferred to attend Columbia.
After weeks of rooting around in his past, in Chicago, in Springfield, in Honolulu, I went to see Obama in his Senate office. He had just returned from the Senate floor to a sparely decorated inner sanctum, notable for a large, bright, almost child-like painting of Thurgood Marshall. After exchanging pleasantries (we have a connection: my sister-in-law, Betsy Myers, a former Clinton-administration official, was chief operating officer of Obama’s campaign; she took the job after I received this assignment, and we have not talked about her new boss since), Obama sat down and put a foot up on the coffee table. Our conversation ranged from Indonesia to Illinois, but my first question was simple: when did he realize that he had an ambition that might be ever so slightly audacious?
“There was a fundamental rupture in my life between Occidental and Columbia, where I just became more serious,” Obama said. While he was in New York, his father died, giving the son “a sense of urgency about my own life.” He added, “Now, that doesn’t mean at that point I somehow instantly had these grand ambitions for political office. But I do think it was at that point in my life—those two years when I was in New York—where I made a decision that I wanted to, I wanted to make my mark.”
He began making that mark in Chicago, the capital of the American black diaspora. Obama arrived not knowing anyone, but ended up finding his life’s work, a deep Christian faith, and the woman who would become his wife and the mother of his two young daughters. Chicago remains his home today. In his work in Chicago, he not only explored his identity as a black American but determined to get the law degree that he believed would best prepare him for a career in public life. Since then, Obama has never veered from the course he set. He became the president of the Harvard Law Review not because he had the best grades (though he had good ones) but because he won the trust of both conservative and liberal factions in an arena in which the arguments were passionate because the stakes were so small. He spurned a sure path to a Supreme Court clerkship, opting instead for a small civil-rights practice, part-time teaching of constitutional law at the University of Chicago, and a contract for Dreams from My Father, his gripping memoir, which was published to general praise in 1995 but then sank from sight for almost a decade.
One of the clearest-eyed grandees of the Chicago establishment, Newton Minow has long seen something special in Obama. Minow played key roles in the two presidential campaigns of Adlai E. Stevenson, then went on to become John F. Kennedy’s chairman of the Federal Communications Commission, famously pronouncing television programming “a vast wasteland” in 1961, a few months before Obama was born. At 81, sitting in his law office at Sidley Austin, in the Loop, above a stretch of street christened Honorary Newton N. Minow Way, Minow is talking about the young man his daughter Martha, a professor at Harvard Law School, recommended for a summer associate’s job two decades ago. At Minow’s firm Obama fell in love with a young lawyer, Michelle Robinson, who would become his wife. Minow acknowledges that he initially opposed two of Obama’s earlier runs for office—his unsuccessful congressional-primary race against the Democratic incumbent, Bobby Rush, in 2000 (the only election for office Obama has lost so far), and his campaign for the Senate, in 2004—and says he asked Obama both times, “Are you nuts?”
Minow opposed Obama’s decision to run for the presidency too, until he caught the senator on C-span during a book-promotion tour in Iowa in late 2006. The formal program was over, but the cameras lingered, capturing Obama’s interaction with the crowd.
“I adored Jack Kennedy,” Minow explains, “and I saw the 21st-century version of Jack Kennedy in my mind. He is astonishing. I think the fundamental point is the country wants a different kind of politics.” He adds, “I also believe the race issue and the gender issue are yesterday, particularly with young people.” One-upping Justice Oliver Wendell Holmes’s famous summary of Franklin D. Roosevelt’s gifts, Minow, a former Supreme Court clerk, says, “I believe as the country sees Barack, gets to know him, they will see the same thing I see: really a combination of a first-class mind and a first-class temperament, all in the same person.”
Dreams from His Mother
Obama owes much of that mind, and that temperament—his spine, his audacity, his empathy—to a person about whom the public knows very little: Ann Dunham, Obama’s mother, who died of ovarian cancer in 1995 at the age of 52. In the preface to the paperback edition of Dreams from My Father, which was first published in hardcover the year his mother died, Obama writes that, if he had known how her life would be cut short, he might have produced a very different book, and he dedicated The Audacity of Hope to his mother and to her mother, Madelyn Dunham, “the women who raised me.”
“I don’t think there’s any question,” Obama said of his mother when we spoke, “she was the most positive influence in my life.”
I went to meet Alice Dewey, a granddaughter of the philosopher John Dewey and an emeritus professor of anthropology at the University of Hawaii, who was the chairman of Ann Dunham’s Ph.D.-thesis committee and became a close friend over many years. “For him, he needed to write the book about his father,” she said of Obama. “But when he says, ‘Who am I?,’ then Ann is a very important part of that.” We were sitting in her cluttered cubby of an office on the campus in Manoa, in the hills above Honolulu. “She was the most hardworking person I maybe ever have met,” Dewey told me. “And did it without seeming to. She was cheerful, down to earth. She absolutely was the kind of person you wanted on your side in any situation, from a barroom brawl to an academic argument, and she was always there for the little guy, particularly the little woman.” For most of the 1970s, 80s, and 90s, she shuttled between Hawaii and Indonesia, doing academic research and paying the bills by teaching English or working for nonprofit organizations such as the Ford Foundation.
Her boldest step of all may have been marrying Barack’s father, a fellow undergraduate at the University of Hawaii, whom she had met in a Russian-language class. Obama has acknowledged that the precise circumstances of their marriage are a bit cloudy, even to him; it would turn out that his father was already tribally married to another woman, in Africa, and after he left Barack and his mother to pursue graduate studies at Harvard on a scholarship, he would marry and divorce another American woman, and then father a child by a second African woman.
Ann Dunham kept up a fond correspondence with Barack’s father, even after her marriage to Soetoro, another foreign student, who eventually went to work for an American company, Union Oil, in Jakarta. She made sure her son knew of his father’s intellect and his government jobs in the post-colonial regime in Kenya, and of the improbable courtship the two had shared. But Obama’s father would remain a distant, intimidating, absent figure, the disappointing details of whose life and career Barack would learn about only much later. “The truth is that none of the men in my life were that successful or that stable,” Obama told me. “They made an awful lot of mistakes.”
It was his mother’s presence—and not infrequent absence—that most colored his early years. She cried easily and remained an impossible romantic. (She would pull her children from bed to look at a particularly beautiful moonrise.) But she also possessed enormous drive and determination. In Indonesia, she would wake Barack up before dawn for English lessons from a correspondence course. Alice Dewey told me that Dunham “divorced happily” from Soetoro—who died in 1987 of complications from a liver ailment—in part because “he gradually became more and more like a Westerner and she became more and more like a Javanese.” Obama told me he could only laugh at the false press accounts that portray Soetoro as some kind of radical Muslim who had sent him to an Islamic school. “I mean, you know, his big thing was Johnny Walker Black, Andy Williams records,” Obama said. “I still remember ‘Moon River.’ He’d be playing it, sipping, and playing tennis at the country club. That was his whole thing. I think their expectations diverged fairly rapidly.”
“She was sort of unflinchingly and unwaveringly empathetic, you know,” her daughter, Maya Soetoro-Ng, who is nine years younger than Barack, told me over coffee one afternoon in Honolulu. “She had an ability to see herself in so many different kinds of people, and that is something she was very strict about with us—that absence of judgment, of acrimony. She was always very good at finding a language that the other person would understand, regardless of where they were from, or their socio-economic background. And I think that’s something that’s been given to us, a major gift that’s bestowed on us.”
The water to Ann Dunham’s fire was her mother, Madelyn, who at 85 still lives in the same high-rise in Honolulu where she helped raise Barack; she is ailing, and declines interview requests. “Barack is interesting,” Maya said, “because he has our mother’s romantic tendencies, but he has our grandmother’s pragmatic tendencies.”
The Dunhams had eloped just before Pearl Harbor, and Stanley enlisted. Madelyn gave birth to Ann living on an army base, and while Stanley served with Patton in Europe, Madelyn was a Rosie the Riveter in a bomber plant at home. “When my grandfather came back, he, by virtue of the G.I. Bill, gets to go to college,” Obama told me. “She doesn’t. She’s working as a secretary.” Stanley Dunham embarked on a peripatetic career as a salesman in Kansas, Texas, Washington, and, finally, Hawaii, where his wife worked her way up about as high as was possible for a woman with no college education. She became the first female vice president of the Bank of Hawaii, and for most of her marriage earned more money than her husband, who ended his days as a kind of Willy Loman in an aloha shirt, dreading the insurance sales calls he had to make. Madelyn insisted on being called Toot—short for Tutu, Hawaiian for “grandparent”—but balked at eating roast pig and poi at her neighbors’, preferring to go home for scrambled eggs and cigarettes.
“She was the opposite of a dreamer, at least by the time I knew her,” Obama said. “Whether that was always the case or whether she scaled back her dreams as time went on and learned to deal with certain disappointments is not entirely clear. But she was just a very tough, sensible, no-nonsense person.” During his teenage years, Obama said, it was his grandmother who “injected” into him “a lot of that very midwestern, sort of traditional sense of prudence and hard work,” even though “some of those values didn’t sort of manifest themselves until I got older.”
“My Afro Stickin’ Up”
The story of Barack Obama’s adolescent struggle with his racial identity, his disquiet, his dabbling with marijuana and cocaine, is by now well known, and well told in Dreams from My Father. His personal page in the Punahou senior yearbook includes not only a picture of him in full Saturday Night Fever leisure suit and wide collar but also a photographic still life of a beer bottle and a pack of Zig-Zag rolling papers. When I mentioned this, Obama laughed and said, “Right, and I’m sure if my mother had had any clue what that was, she would not have been pleased.”
Less well known, but perhaps more revealing, is just how tough the young man then known as Barry had to have been to hide his deepest feelings from the wealthy world around him at Punahou, which had been founded for the children of white missionaries in 1841. No one among the many classmates and teachers I talked to remembers ever seeing any sign of the boy who avoided the only other black kid in his fifth-grade class (“as if direct contact would only remind us more keenly of our isolation,” he later wrote), chafed at the use of the n-word by an ignorant coach, and immersed himself in the writings of James Baldwin, Ralph Ellison, Langston Hughes, and Malcolm X, only to find “the same anguish, the same self-doubt, a self-contempt that neither irony nor intellect seemed able to deflect.”
“We were shocked beyond imagining that he was unhappy,” one of his classmates, Kelli Furishima, who now manages a kitchen-supply store in Honolulu, told me. “He carried himself comfortably at all times.” Eric Kusunoki, who was Obama’s homeroom teacher during all four years of high school, and still teaches at Punahou, told me that he never picked up any hint of Obama’s feelings: “He never let on,” says Kusunoki.
The school was, and is, happily multicultural, but its corny cheer is a white-bread chant, whose origins are murky, even to school officials: “Strawberry shortcake, huckleberry pie! / V-I-C-T-O-R-Y! / Are we in it? Well, I guess! / Punahou, Punahou, yes, yes, yes!” When I asked Obama about this, he just smiled and said, “What can I tell you?”
The school’s style of basketball was just as vanilla. “His game didn’t really fit our system,” recalled Alan Lum, a teammate who now teaches second grade at Punahou. “We ran a structured offense. We were very disciplined. Barry, he did a good job with that, but he was a very creative player, you know? I guess a lot of his best days were on the outside courts, playing with friends.” Obama acknowledged as much. “Basketball was a good way for me to channel my energy,” he said. “It did parallel some of the broader struggles I was going through, because there were some issues in terms of racial identity that played themselves out on the basketball court. You know, I had an overtly black game, behind-the-back passes, and wasn’t particularly concerned about fundamentals, whereas our coach was this Bobby Knight guy, and he was all about fundamentals—you know, bounce passes, and four passes before you shoot, and that sort of thing. So we had this little conflict that landed me on the bench when I argued.
“The truth was,” Obama continued, “on the playground, I could beat a lot of the guys who were starters, and I think he thought it was useful to have me there in practice.”
If most of Obama’s friends did not know his deepest feelings, he nevertheless managed to let some of them show, in writing, as he did in this poem for the school literary magazine, Ka Wai Ola:
I saw an old, forgotten man
On an old, forgotten road.
Staggering and numb under the glare of the
Spotlight. His eyes, so dull and grey,
Slide from right to left, to right,
Looking for his life, misplaced in a
Shallow, muddy gutter long ago.
I am found, instead.
Seeking a hiding place, the night seals us together.
A transient spark lights his face, and in my honor,
He pulls out forgotten dignity from under his flaking coat,
And walks a straight line along the crooked world.
Kelli Furishima showed me the poem, marveling, “And he was a jock!” Furishima also showed me, but asked me not to quote verbatim, the tender inscriptions in her yearbooks from Obama, who, in tiny, precise architect’s printing, expressed regret that they hadn’t gotten to know each other better, and the hope that someday he might be worthy of her attention. He signed one of them, at the very bottom of the page, with a squiggly cartoon of a mound protruding from the edge of the paper, and these words: “
When I mentioned the poem to Obama, he at first had no memory of it. After I read it to him, he said, “That’s not bad. I wrote that in high school? You know, it sounds in spirit that it’s talking a little bit about my grandfather.”
Obama acknowledged that the first years of college were simply an extension of “a cloudy period of, you know, having too much fun.” But then, he told me, his mother’s values began resurfacing, and in New York he could not ignore the obvious strains and tensions of urban life, or the tensions within his own. By the time he had finished Columbia, spent a year working as a writer and financial analyst for the publishing and consulting firm Business International Corporation, and gotten his first taste of community action, in Harlem, he knew what he needed to do: “I wanted to devote myself to something larger than making money or having a good time.”
A Really Tough Crowd
Obama embarked on what he says, even now, was the hardest work of his life: the three and a half years of community organizing in the impoverished neighborhoods of Chicago’s far South Side. His job: to work with the Developing Communities Project, a church-based effort that aimed to organize low-income residents to improve local conditions. The challenges were huge. He knew no one. He was in search of his own identity as a black man, but was greeted quizzically by some black ministers, who did not see why they should make common cause with the white Catholic clergy working with the organization. Congregants of every denomination wondered why Obama did not have a church of his own. It was a test of both mettle and resilience. Gerald Kellman, who hired Obama and is now an adult-Christian-education teacher in a Catholic parish outside Chicago, told me, “Barack never had any practical political experience before coming to Chicago, and that was one of the things he learned about, and he learned very quickly.” Kellman added, “In part, that was a conscious decision: that idealism only takes you so far.”
Even as he confronted the limits of community action, Obama was confronting the limits of his own father’s achievements. It was in Chicago that he was first visited by Auma, his older half-sister from his father’s first marriage, in Africa, and began to understand that the figure he knew mostly from letters and his mother’s lionizing memories had in fact died a broken man, his once bright hopes dimmed by political and personality conflicts with the Kenyan regime, and his personal life a shambles of drinking and family dysfunction. Obama visited Kenya, met his extended family of half-siblings, and began to make peace with his father’s memory. His father’s story became “an object lesson,” Obama told me. “I saw the pain of my sister and my brothers on my father’s side. I mean, they had a tough time; they had a much tougher time than I did. And I think it’s fair to say—and it’s a hard thing to say—but I was probably lucky not to have been living in his house as I was growing up. I do think that part of my life has been a deliberate attempt to not repeat mistakes of my father.”
Michael Kruglik, a fellow organizer, was struck by Obama’s intensity and toughness. “I was sort of amused, almost, by this debate about: Is he black enough?,” Kruglik said, referring to the contention of some critics that because his ancestors were not slaves Obama lacks the authentic experience of other American blacks. “Because if you saw the way he was then, he didn’t go around saying, ‘I’m a young black man on a search for identity.’ What he did was he said, ‘I’m here and I want to get something done.’ ” Kruglik added, “I wouldn’t use the phrase, because it probably doesn’t have the currency now, but there was a certain edge on it. It’s not a militancy. But it was an intense commitment, and an intense vibe, that came off him.”
By the time Obama decided to go to Harvard Law School, in the winter of 1988, he knew he wanted a career in the public arena. “I think Barack realized how much more useful he could be if he was actually inside, trying to make the system change, rather than trying to push it from the outside,” his friend Valerie Jarrett, former chairman of the Chicago Stock Exchange, told me. Obama himself described the years in Chicago to me as the time when he “finally and fully grew up.”
At Harvard, Obama shone as never before, though without seeming to show off. Jackie Scott Corley, now a law clerk to a judge in San Francisco, who knew Obama at Harvard, says, “I’ve never been in a place with a larger collection of egos. Lawyers, in particular, are already Type A. He stuck out as putting himself apart from that.” In his second year, he ran for president of the Law Review, and after a marathon voting session was elected on the 19th ballot, as an overt compromise candidate.
Nancy McCullough, an entertainment lawyer in Los Angeles, was a year behind Obama at Harvard and recalls him as “someone who wanted the group decisions to reflect the group’s intent, not Barack’s intent. One of the reasons people were comfortable putting him in the presidency was because he was going to listen closely enough that, whatever decisions had been made, people would know that he had [listened]. He was masterful in how he facilitated people’s talking.
“I actually would have been happier for him to say sometimes, ‘This is how we’re doing this, and shut up!’ ”
Obama himself made it clear that his ambitions were growing, that maybe it was time to start getting his hands on some pow-er. “I probably figured I would practice law for a while but then be part of some large-scale community-rebuilding effort, maybe running a large not-for-profit, or setting up a large not-for-profit, that could tackle some of the issues I’d been dealing with,” he told me. “But I don’t think at that point that I was absolutely focused on politics. I did think that there would be a possibility that at some point I’d be interested in politics.” And he added, “Sometimes I look back on letters I wrote, or notes, and I think there is a vague sense that at some point I might run for public office, but it wasn’t a systematic plan that I’d come back and work for three or four years and run for state senate and then go for the mayor’s seat. I don’t think it was that worked out.”
“Let Him Wait His Turn”
Obama returned to Chicago and began work on the book he had decided to write, about his search for the meaning of his father’s life, and his own. He joined the civil-rights law firm presided over by Judson Miner, who had been Harold Washington’s corporation counsel, and began teaching constitutional law part-time at the University of Chicago. In 1992, he served as executive director of Illinois Project Vote!, a voter-registration drive that added an estimated 125,000 black voters to the rolls and was credited with helping elect Carol Moseley Braun to the U.S. Senate.
Four years later, in 1996, Obama ran for the state senate himself. He played hardball, not only knocking Alice Palmer, the incumbent, off the ballot for not receiving enough valid signatures on her nominating petitions, but clearing the field of all other rivals too. By this time, Obama told me, he was “fairly practical” and “pretty mindful of wanting to forge alliances with people, even unexpected folks.” Yet he was also ambitious. One of his first moves was to co-sponsor a measure that would have amended the Illinois state constitution to make health care a fundamental right. Needless to say, it failed. But by the time Obama left Springfield, eight years later, he had managed to pass a measure mandating a study of a path to universal coverage, one that is bearing fruit in current proposals by the Democratic governor.
What Obama did best in Springfield, with the help of Emil Jones, was to rack up the kinds of small but measurable achievements that could further his ambition. “What I was able to do was to position myself as the negotiator for the Democrats on certain issues, where the Republicans were willing to give some cooperation,” Obama recalled. Jones says he promptly put him in charge of carrying the Democrats’ water in negotiations on the first overhaul of state ethics laws in 25 years, and on a revamping of the state’s welfare laws. Neither measure went as far as purists in both parties wished: the ethics measure’s ban on lawmakers’ personal use of campaign funds exempted existing accounts, for example. But Obama made friendships across the aisle.
In 2000, Obama made the one genuine miscalculation of his career: he decided to challenge Bobby Rush, the incumbent congressman from Chicago’s South Side and a former Black Panther, in the Democratic primary. He was not alone; Donne Trotter, a fellow black state senator, also entered the race, which meant that Emil Jones had to remain neutral. There were plenty of reasons not to run, but Obama was restless. “Bounce passes, and four passes before you shoot”—it wasn’t his kind of game.
“You’re in the minority and you’re looking to get out of there,” Obama’s colleague John Cullerton, a member of an old political family who himself once challenged the venerable incumbent Dan Rostenkowski in a primary, told me. He added, “The thought was: these chances don’t come along very often, and if you pass up the opportunity, you think of yourself being on a porch at 70, thinking, I really could have run. The other thing that motivates you is you really think you’re better than the other guy.” Obama clearly thought he was better than Rush, who, he argued, hadn’t done a lot for the district. Much of the black establishment felt otherwise. “I called every black friend I knew in town, successful businessmen,” Newt Minow recalled. “They said, ‘Let him wait his turn.’ He lost. I think that was a very good thing for him.”
Two years later, the Democrats took control of the legislature and Obama saw another opportunity. Peter Fitzgerald, the rich but lackluster Republican who had held one of the state’s two seats in the U.S. Senate for a single term, looked vulnerable in 2004 (and, indeed, opted to retire). Obama told Michelle his would be an “up or out” strategy, and he needed to get some things done. He found a willing ally in Cullerton, who represented North Side neighborhoods and was the newly named chairman of the Judiciary Committee. Their agenda included the death penalty, then among the hottest issues in the state. After widespread evidence of wrongful convictions, the Republican governor, George Ryan, first suspended executions, then commuted the sentences of some 150 inmates on death row. He appointed a task force that included the novelist Scott Turow to make recommendations for reform. But the G.O.P.-controlled legislature had not taken action by 2002, when Ryan, his administration beset by corruption scandals, chose not to run again, and Democrats took the governorship for the first time in 25 years, also taking control of the state senate.
Cullerton and Obama teamed up. They faced stiff opposition—from abolitionists on the left, who didn’t want “improvements” in capital punishment, because they wanted to end it, and from a broad group of police and prosecutors on the right. Obama took on a particular and pioneering measure to require videotaping of interrogations and confessions in capital cases. Laboriously, he negotiated compromises—such as giving judges discretion in administration of the program—that persuaded the police and prosecutors to go along. The measure passed overwhelmingly.
“He took it on when everyone else said it was a complete nonstarter, and in fact no one would touch it with a 10-foot pole,” Cornelia Grumman, an editorial writer for the Chicago Tribune who won a Pulitzer Prize for her commentary on the subject, recalls. “But he worked it, and worked it, and went back and forth for months and months between the Fraternal Order of Police and the State’s Attorneys Association, and to the reformers, and then to the Chiefs of Police, and then back again to everyone. And he really skillfully negotiated that stinker into an actual bill.”
By then the Senate race was crowded, dominated by two independently wealthy newcomers to politics: on the Democratic side, Blair Hull, a former securities trader who had made his first stake playing blackjack and pumped $29 million of his own money into the race, and for the Republicans, Jack Ryan, a former Goldman Sachs investment banker who had made a fortune and then spent time as a teacher in an inner-city Catholic school. Another Democratic contender was the state controller, Dan Hynes, from an old Chicago political family, who figured to have strong labor and organization support.
But Obama had his own ace: Emil Jones, whose support had the effect of tying the hands of Mayor Richard Daley and Governor Rod Blogojevich. “He knew if he had me in the run for the Senate, it would put a block on the current mayor,” Jones recalled. “The current mayor and the father of the controller, which was Dan Hynes, they were roommates in Springfield when the mayor was a state senator, so they had a relationship. Another big financial backer for the governor was Blair Hull. Barack knew if he had me it would checkmate the governor, ’cause the governor couldn’t come out and go with Blair Hull, ’cause the governor needs me. Same with the mayor. So he had analyzed and figured all of that out. He knew I could help him with labor support. And I could put a checkmate on some of the local politicians that didn’t know him, but they couldn’t really go against me. It was just like in a football game: you got this talented running back, but without those linemen opening the holes and blocking, the running back would never get out of the backfield.”
Obama secured the nomination and in November 2004 won election to the Senate.
In his Springfield hotel room one night that summer, watching a basketball game on TNT, Obama began, as he recalled, “jotting down some notes,” some thoughts about what he’d seen so far in his Senate campaign, incorporating parts of the stump speech that he’d developed. “Wrote it on the back of, I think, a schedule and some legal pads,” he told me, recounting the tale with the easy assurance of someone who might write the speech of a lifetime on, say, the back of an envelope. But Obama’s words in this instance were no idle jottings. He had been asked by John Kerry to deliver the keynote address at the Democratic National Convention, in Boston, in July. This is the speech in which Obama declared, “We worship an awesome God in the blue states, and we don’t like federal agents poking around in our libraries in the red states. We coach Little League in the blue states and, yes, we’ve got some gay friends in the red states.”
Obama’s good friend Martin Nesbitt, a successful black businessman in Chicago, spent the day of the speech with him, traveling from appearance to appearance. “We were walking down the street in Boston, and this crowd was growing behind us, kind of like Tiger Woods at the Masters. And I turned to Barack and I said, ‘This is incredible. You’re like a rock star.’ And he looked at me and said, ‘If you think it’s bad today, wait till tomorrow.’ And I said, ‘What do you mean?,’ and he said, ‘My speech is pretty good.’ ” It was an extraordinary display of self-confidence, and self-knowledge. “All of the rest of us are groping as to how to handle this, because we couldn’t ever imagine we’d be in this place we’re in,” Obama’s brother-in-law Craig Robinson told me. “I think the way my sister is processing it is day by day. I think the way that Barack is processing it is as just another step in his strategic plan.”
It has become all but impossible to mention Obama without invoking the name of his fellow Illinoisan Abraham Lincoln, however preposterous the comparison might seem at first blush. Obama himself is not so presumptuous as ever to liken himself to Lincoln, but he unself-consciously summons Lincoln’s legacy, as he did when announcing his candidacy on the grounds of the Old State Capitol, in Springfield.
What Obama did not mention—and what is so easy to forget about the holy Lincoln of hagiography, and the melancholy Lincoln of martyrdom—was Lincoln’s steely ambition, the conviction from an early age that he was destined for great things, and the cold political calculation that enabled him to beat out a half-dozen more experienced and ostensibly better-qualified men. These were the people that the historian Doris Kearns Goodwin has memorably called Lincoln’s “team of rivals.” And the Lincoln to whom Obama might be plausibly compared is not the Lincoln of statuary and the Second Inaugural but the circuit-riding prairie lawyer of John Ford’s Young Mr. Lincoln, or the searching, questing Lincoln of Robert E. Sherwood’s Pulitzer Prize–winning Abe Lincoln in Illinois, produced on Broadway on the eve of World War II.
That Lincoln was the young, improbable character described by his law partner, William Herndon, as “the most ambitious man in the world.” His cousin Sophie Hanks said of Lincoln that he “always had a natural idea that he was going to be something.” In 1832, at the age of 23, still struggling to master English grammar and after only six months’ residency in New Salem, Illinois, Lincoln ran for the state legislature. He lost, but took 277 out of 300 votes cast in his adopted village. Two years later, he ran again, and this time won, and two years after that he had this to say to an older, more experienced man who challenged his re-election: “The gentleman has seen fit to allude to my being a young man; but he forgets that I am older in years than I am in the tricks and trades of politicians.” Sound familiar? Lincoln’s folksy stories masked his cunning, and his tenderheartedness sometimes concealed his ambition. But both were there in full measure, and long had been. Lincoln set about at a very young age to find his place in the world, and with the conviction that his rightful place would be one of great significance.
On February 11, 1861, the day before his 52nd birthday, Lincoln left Springfield to assume the presidency, and as he did so he made one of the most eloquent speeches of his eloquent life, summing up his feeling for the place that had made him. “Here I have lived for a quarter of a century, and have passed from a young to an old man,” he is reported to have said. “I now leave, not knowing when, or whether ever, I may return.”
Obama’s own farewell to his colleagues in Springfield, on November 8, 2004, was less eloquent but no less heartfelt. Afterward, he faced the Springfield press corps for the last time. Someone asked why he had already ruled out running on a national ticket with Hillary Rodham Clinton in 2008. His answer was crisp and immediate. “You know,” Obama replied, “I am a believer in knowing what you’re doing when you apply for a job. And I think that if I were to seriously consider running on a national ticket I would essentially have to start now, before having served a day in the Senate. Now, there are some people who might be comfortable doing that, but I’m not one of those people.”
But he is one of those people. He is. And wherever he is going, he has been one of them for a long, long time.
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