Barack and Michelle Read online

  Barry’s Pakistan connection would continue even after he arrived in New York. Unable to get into the cold-water flat he had arranged to rent on 109th Street in Spanish Harlem—he would spend his first night in Manhattan huddled with his belongings in an alley—Barry called up the only person he knew in the city for help.

  Barry had met Pakistani Sohale “Hal” Siddiqi a year earlier, when Siddiqi was visiting his friends Hamid and Chandoo in Los Angeles. Now Siddiqi was making ends meet working as a salesman at a boutique during the daytime and as a waiter at night.

  “He arrived disheveled and without a place to stay,” Siddiqi said. Instantly, Siddiqi recognized something of himself in the homeless African American. “We were both very lost,” he said. “We were both alienated.”

  Siddiqi took Obama in, helped him move into the Spanish Harlem apartment a few days later, and then helped him move out when it turned out the apartment had no heat. Together, they found a sixth-floor walk-up on East Ninety-fourth Street between First and Second Avenues—but there was a catch. In order to secure the lease, they would both have to show they were financially stable. Obama refused to lie on the application—he put down that he was a Columbia University student with no income—leaving it to Siddiqi to falsely claim that he earned a substantial salary working for a high-end catering firm.

  Barry, despite his refusal to participate, was fully aware of the subterfuge. “We didn’t have a chance in hell of getting this apartment unless we fabricated the lease,” Siddiqi said. “So I was the one who had to do it.”

  A Park Avenue penthouse it wasn’t. Drugs were sold on the stoops of neighboring buildings in broad daylight, and gunshots punctuated the night. The apartment itself was a dark, cramped, postage-stamp-sized one-bedroom with leaky pipes, noisy radiators, and paint peeling from the ceiling. There was no money for furniture. The two men slept on mattresses on the floor; the living room couch and chairs were picked up off the street. There were no tables at all. They and anyone who happened to visit them ate from paper plates balanced on their laps.

  This spartan existence was all in keeping with Barry’s plan. He had actually begun reinventing himself the minute he arrived in Manhattan. Relocating to New York, he said later, “was a really significant break. It’s when I left a lot of stuff behind.” His name, for instance. From this point on, if anyone asked how he wished to be addressed, the answer was always the same: “Call me Barack.”

  This change was not, he later insisted, “some assertion of my African roots—not a racial assertion. It was much more of an assertion that I was coming of age. An assertion of being comfortable with the fact that I was different and that I didn’t need to try to fit in in a certain way.”

  Most important, Barack now eschewed the alcohol and drugs that had threatened to derail his life—“the final, fatal role,” he wrote, “of the young would-be black man.” There would be no more weekend bacchanals, no more Mexican maids throwing up their hands in despair.

  For the next two years, Barack embarked on a lifestyle that bordered on the monastic. He fasted on Sundays, and for the rest of the week adhered steadfastly to Dick Gregory’s vegetarian diet. Gone were the blazers and neatly pressed khakis of his prep school days, now replaced by a navy surplus peacoat worn with Levi’s and a turtleneck picked up at the Salvation Army for five dollars. “I think self-deprivation was his shtick,” Siddiqi recalled, “denying himself pleasure, good food and all of that.”

  Siddiqi made up for his roommate’s self-imposed asceticism. He drank, smoked pot, and did lines of cocaine with friends in their apartment. He continually offered Barack drugs, and every time, according to Siddiqi, he refused.

  For the most part Barack was, by his own admission, leading “a pretty grim and humorless” life. His routine consisted of getting up and running three miles, attending classes at Columbia, then coming home to spend hours reading. Any free time was spent aimlessly wandering the streets. His exploration of the city—from the stately limestone mansions and brick town houses of the Upper East Side to Chinatown and the Financial District to the slums of Harlem and the South Bronx—served only to underscore the inequities of American life and fuel his growing despair. He now began to keep detailed journals, which he filled with his observations and his poetry. “Strange,” he wrote after yet another cabdriver drove past him to pick up someone else. “Don’t they see my white relatives?”

  When Barack did bother to venture outside the little world he had created for himself, it was to lecture Siddiqi and anyone else he came in contact with about the plight of the world’s poor and the failure of Western societies to do anything about it. Predictably, Siddiqi, whose own goal in life at the time “was to make a lot of money to buy stuff,” grew tired of Barack’s sermonizing.

  “Who do you think you are, Barack? A saint?” Siddiqi asked. “Why are you so serious all the time?” Then he delivered the coup de grâce. “Barack,” Siddiqi said with a sigh, “you are becoming a bore.”

  Perhaps. But Barack wasn’t, Siddiqi hastened to add, “entirely a hermit” during this period. He would invite friends over to the apartment and relax on the floor listening to Van Morrison, Ella Fitzgerald, Bob Dylan, Stevie Wonder, and his new favorite, Billie Holiday. Nor had he given up his principal vice: smoking. “He’d be sprawled out on the couch,” Siddiqi recalled, “listening to his music and blowing smoke rings in the air.”

  There was something else Barack was not entirely willing to give up. He would join friends for a night out every now and then, and even went cruising some of the East Side’s more notorious singles bars with Siddiqi. “We were always competing,” recalled Siddiqi, who claimed that several of his female friends told him they considered Barack “a hunk.” Although Barack still abstained from alcohol, he and his roommate would, said Siddiqi, “go to bars and try hitting on the girls. He had a lot more success. I wouldn’t outcompete him in picking up girls, that’s for sure.”

  Years later, Barack would write that during this time he had a yearlong affair with a wealthy young white woman who had “dark hair, specks of green in her eyes. Her voice sounded like a wind chime.” The romance ended, he claimed, after he visited the young lady’s stately country home, looked around at the photographs of Presidents, Senators, and industrialists that hung on the walls, and decided he could never be a part of her world. The actual breakup, as Barack would describe it years later in his book Dreams from My Father, supposedly took place in the street after he had taken her to see a new play by an angry young black playwright. “She couldn’t be black, she said,” Barack wrote. “She would if she could, but she couldn’t. She could only be herself, and wasn’t that enough?”

  Barack then observed that even if she’d been black it wouldn’t have worked out. “I mean,” he wrote, “there are several black ladies out there who’ve broken my heart just as good.”

  No one, including his roommate and closest friend at the time, Siddiqi, knew of this mysterious lover’s existence—or could recall Obama’s heart ever being broken by a woman regardless of her race. Not that Barack had taken a vow of celibacy—far from it. “One-night stands,” a barhopping friend remembers. “That seemed to be pretty much it.”

  Neither his mother, Ann, nor his sister Maya encountered any of Barack’s women friends when they visited him that first summer in New York. Thanks in part to Ann’s enduring fascination with all things Third World, they hit it off instantly with Barack’s free-spirited Pakistani roommate.

  The same could not be said for Siddiqi’s mother when it was her turn to visit from Pakistan. Having never known a black person, she treated Barack with contempt. “My mother was terribly rude to him,” Siddiqi admitted. Barack reacted by being “so polite and kind to her.”

  Accordingly, Siddiqi was there for Barack in November 1982 when the call came from Africa that would change Obama’s life forever. As he so often did, Barack senior had been out carousing with friends in the honky-tonk town of Kaloleni, this time celebrating rumors t
hat he was soon to be given a big promotion. Having already lost both his legs in another one of his accidents and now walking on crude prosthetic limbs, he was driving himself home but never made it. Veering off the road, he crashed into the six-foot-high stump of a giant gum tree and died instantly. He was forty-six.

  Barack was frying eggs in the tiny kitchen of his apartment when his Aunt Jane, a woman he had never met, phoned with the news. “Listen, Barry, your father is dead,” Aunt Jane said. “He is killed in a car accident. Hello? Can you hear me?”

  Barack scarcely knew how to react. His father remained a myth to him—“both more and less than a man”—and because of that he would later say he felt “no pain, only the vague sense of an opportunity lost.” When he called his mother to tell her Barack senior had been killed, she cried out in anguish.

  Barack senior was buried in the village where he was raised, Nyang’oma Kogelo. Attending the funeral were several top government ministers, as well as more than forty members of Obama’s extended family. His American son was not among them.

  Siddiqi, meanwhile, continued his wanton ways. “I was partying all the time,” he said. “I was disturbing his studies.” Barack needed to be free from unnecessary distractions; he had settled on a major—political science, specializing in international relations—and was now heading down the home stretch toward his degree.

  Frustrated that Barack would not loosen up, Siddiqi accused him of kowtowing to his white professors. “Look at you,” Siddiqi sniped. “You’re nothing but an Uncle Tom.” He would deliver this particular zinger on several occasions, and each time his target reacted the same way—with benign indifference.

  Indeed, Barack’s fabled unflappability was already very much in evidence. One morning he and Siddiqi were walking Siddiqi’s pug, Charlie, on Broadway when a hulking street person approached them and began stomping on the pavement next to Charlie’s head. Siddiqi angrily confronted the homeless man, and as the two men squared off, Barack suddenly stepped between them. “Hey, hey, hey!” Barack said, shoving his face right into the stranger’s. The man looked into Obama’s eyes and backed down. “It was an incredible scene,” Siddiqi said. “Barack could be pretty fearless. He always stood up for what he thought was right.”

  Still, Barack could not put up with his friend’s undisciplined behavior indefinitely. By the start of his senior year, he had moved out of the East Ninety-fourth Street apartment and in with a new roommate. “Barack was really patient,” Siddiqi later said. “I’m surprised he suffered me as long as he did.”

  Barack could not always count on friends. But he knew that the people he considered at the time to be his only real family—his mother, Maya, Gramps, and Toot—would be there for him when, in June of 1983, he graduated from Columbia University with a degree in political science.

  During his waning days at Columbia, he had nurtured dreams of becoming a community organizer—although he was not precisely sure what a community organizer actually was or what the job entailed. “I’ll organize black folks,” he told himself. “At the grass roots. For change.”

  For Barack, organizing would be no less than “an act of redemption”—a chance to earn, through shared sacrifice, “full membership” in the black community. He thought back to the “sit-ins, the marches, the jailhouse songs” of the civil rights era and imagined himself there—only this time fighting for the social, economic, and political rights of a new generation.

  In the spring of 1983, Barack fired off scores of letters to black politicians, civil rights organizations, and neighborhood, tenants’ rights, and community action groups around the country. He was a young black progressive-minded Ivy League graduate, he told them, and he was eager to do whatever he could for the cause.

  He received not a single reply. Undaunted, he decided instead to take a job that would pay the bills while he waited for some discerning activist group to take him up on his offer. He promptly landed a job as a research associate at Business International Corporation, a small publisher of newsletters tracking the activities of corporations operating overseas (a few years later the firm would be acquired by Britain’s The Economist Group).

  Barack would later describe Business International as a leading consulting house where, in order to fit in, he wore a power suit and carried a briefcase. Not so, according to those who worked with him. “It was a bit like a sweatshop,” said one of his BI coworkers, Dan Armstrong. “I’m sure we all wished that we were high-priced consultants to multinational corporations. But we also enjoyed coming in at ten, wearing jeans to work, flirting with our coworkers, partying when we stayed late, and bonding over the low salaries and heavy workload…. Barack never wore a tie, much less a suit. Nobody did.”

  Like others who worked alongside Barack then, Armstrong found him to be “aloof—reserved and distant with his coworkers.” Another BI coworker, Bill Millar, went a step further. “I worked next to Barack nearly every day he was at Business International,” said Millar, who had a degree in finance and Wall Street experience. “I found him arrogant and condescending. He just sort of rolled his eyes if you tried to explain something to him. I’ll never forget it.”

  Nevertheless, within a few months Barack was promoted to financial writer, contributing articles to one of the firm’s key newsletters, Business International Money Report. He was also put in charge of editing the company’s global reference service, Financing Foreign Operations, and given a substantial raise. (He was not assigned his own secretary, however, as Barack would later claim. “The idea that Barack had a secretary is laughable,” Armstrong said. “Only the company president had a secretary.”)

  BI’s informal atmosphere aside—a former top executive of the firm called it “high school with ashtrays”—the fact remained that twenty-two-year-old Barack was the firm’s only black executive. All the other African Americans he encountered at Business International were secretaries, receptionists, mail-room clerks, and security guards—the men and women who were indispensable to the entire operation but seldom given the opportunity to rise above their station.

  Barack felt more than a little self-conscious about his management position, but he could not afford the luxury of feeling guilty. The women in the secretarial pool and the other black staffers were all rooting for him to succeed. Whether he liked the work or not, he was, for the time being at least, determined not to disappoint them.

  Barack kept toiling away at his Wang computer terminal until he received yet another wake-up call from Africa. This time it was his half sister Auma, Barack senior’s daughter by his first wife, choking back tears as she delivered more bad news. Their half brother David, Barack senior’s son by his third wife, Ruth Nidesand, had been killed in a motorcycle accident.

  Barack had never met David, but news of his brother’s sudden and shocking death rekindled his desire for “redemption” through community organizing. After a little more than a year laying the foundation for a climb up the corporate ladder, Barack quit his job at Business International.

  For the next three months, he worked as a community organizer for Ralph Nader’s New York Public Interest Research Group out of the Harlem campus of the City College of New York. He quickly discovered that students—even minority students—were less interested in protesting against the Establishment than they were in joining it. “A good job in corporate America, a fat paycheck, and nice things—that’s what they all want,” he told a fellow activist. “Can you blame them?”

  Of course, Barack had willingly given up all those things, and by the late summer of 1985 he was broke. It was then, while perusing a publication called Community Jobs, that he spotted a want ad offering a position as a community organizer trainee in Chicago. Barack answered the ad immediately, sending along his résumé. Within a week he found himself sitting in a Lexington Avenue coffee shop on the Upper East Side with the man who had placed the ad, Jerry Kellman.

  The ad had been an act of desperation for Kellman, a stocky, not quite middle-aged man who
looked like he had spent the night on tumble dry. Beginning with the campus antiwar movement in the 1960s, Kellman had spearheaded one social protest after another, and in the process built a reputation as one of the Midwest’s most effective community organizers.

  Now Kellman faced his most daunting challenge yet. Chicago was hemorrhaging manufacturing jobs, driving more of the city’s urban working class into unemployment and poverty. Unions no longer had the clout they once had, so now Kellman was trying to convince Chicago’s powerful black churches to stand up to the corporations on the workers’ behalf.

  Trouble was, Kellman and his colleagues were white and, for the most part, Jewish. Black pastors on Chicago’s South Side were suspicious of their motives. “Here we were trying to organize in Chicago’s African American community,” Kellman said, “and we didn’t have any African Americans on our staff. It did not look good, obviously.”

  Before their meeting in the coffee shop, Kellman had interviewed Barack on the phone for nearly two hours. “He was clearly very bright,” Kellman remembered. “But there are a lot of very bright young people out there. But he was also mature, confident, articulate.”

  Kellman was particularly intrigued by Barack’s upbringing. “His father had left the family, his mother wasn’t around a lot, he moved from one culture to another—and it all left him feeling like an outsider,” Kellman said. “Outsiders can do one of two things: they can try to join the mainstream or they can identify with the other outsiders. Barack identified with the other outsiders. That was important.”

  Satisfied that Barack was the right person for the job, Kellman came right to the point during their face-to-face meeting. “I can’t break through,” Kellman admitted to Barack. “So that’s why I need someone like you.”

  Barack, Kellman later said, “was looking for the civil rights movement, but it was over. Organizing was the closest thing he could find to it.” Barack was also looking to avoid the mistakes made by his father. “My father was a brilliant man, an intellectual,” Barack told Kellman. “He returned to Kenya bursting with ambition to do things for his native country, but he didn’t know how to turn his ideals into reality. So he ended up just another bitter, broken bureaucrat with a drinking problem. I am not,” Barack vowed, “going to end up like my father.”