On a stiflingly hot July weekend just two years earlier, Barack senior was shopping in Nairobi when he bumped into his old mentor Tom Mboya. “You are parked on a yellow line,” Barack senior joked with Mboya. “You’ll get a ticket.” Minutes later, Mboya was gunned down on the street.
Barack, who worked in Kenya’s Ministry of Economic Planning and Development, had already infuriated his superiors by publicly criticizing his government’s economic policies and for complaining that he was working for men less capable than he was. Now he risked angering powerful forces in the Kenyan government by testifying at the trial of Mboya’s accused assassin.
On the basis of Barack senior’s testimony and that of nine other eyewitnesses, Mboya’s killer was tried and hanged. But from that point on, Obama’s career—and life—began to spiral out of control. On a visit to Nairobi’s Ministry of Economic Planning and Development, American international development expert Clive Gray noticed Obama lurching down a hallway.
“What’s the matter with that guy?” Clive asked a ministry staff member. Obama had changed so dramatically that Clive hadn’t recognized him at first.
“He is always very intoxicated,” the staffer replied, “and unable to do his job.”
Although the senior Obama had impressed Gray as “kind of a loudmouth” when he first encountered him at Harvard, he remembered how much promise the young Kenyan had shown back then. Looking at him now, Gray could hardly believe that this was the man who had vowed to save his country from economic ruin. “It was,” Gray said, “very sad.”
Although he did not share the details with either the Dunhams or his son, Barack senior had been driving drunk when he slammed into a tree and badly fractured his leg. It was only the latest in a series of accidents involving alcohol that left Barry’s dad with a permanent limp.
Barry was understandably horrified when he learned that his father had accepted an invitation from his fifth-grade homeroom teacher, Mabel Hefty, to speak to her pupils. But by the time Barack senior had finished telling Barry’s class about the wonders, challenges, and mysteries of life in Africa—about tribal customs, wildlife, and Kenya’s own struggle against the British for independence—his son was beaming with pride.
It was, Barry would recall, a “tortured moment” that ended with “tremendous relief” that his father had managed to impress teachers and students alike. “That he’s different, but is somehow able to communicate with great confidence a sense of common humanity was actually a great object lesson for me.”
At home, however, Barack senior’s humanity was somewhat less evident. Barry had eagerly anticipated watching Dr. Seuss’s How the Grinch Stole Christmas on television—a holiday tradition in the Dunham household—but instead was ordered by his father to do his homework. “I tell you, Barry, you do not work as hard as you should,” he said. “Go now, before I get angry at you.” From that point on, Barry could not wait for his father to leave.
That Christmas visit would last scarcely four weeks. Despite the tensions with Barack senior and the fact that both his parents were married to other people, Barry would treasure this as the only time he could recall being together with his father, mother, and grandparents as a family unit.
What Barry did not know at the time was that his father had pleaded with his mother to return with him to Africa—and to bring Barry and Maya with her. Ann, who was aware that Barack senior already had at least two wives and a half-dozen children waiting for him back home, declined.
When his father and mother both left—he bound for Kenya, she for Indonesia—Barry tried to accept the separation as “just the way things were.” But later, he would confess, “I suspect it had more of an impact than I know.”
Ann promised her son that she would return to live with him in Hawaii the following year. In the meantime, his character would continue to be molded and shaped to a large extent by Toot and Gramps.
Now occupying a modest two-bedroom apartment just ten minutes away from Waikiki, on Beretania Street in Honolulu’s Makiki neighborhood, the Dunhams were going through some trying times of their own. Without the ability to literally pump someone’s hand or look that person in the eye as he told one of his over-the-top stories, Gramps quickly discovered that he just wasn’t cut out for life as a telemarketer. “Of course, people were hanging up on him all the time, or making excuses for why they were too busy to see him,” said a family friend. “It was really killing him slowly inside, making him very resentful—especially toward Madelyn.”
The Dunhams were secure financially—thanks to Toot’s steady rise at the Bank of Hawaii. She now earned far more than her husband, despite the fact that the male executives she was training were often promoted ahead of her and invariably paid fatter salaries. It was a commonly seen brand of overt corporate sexism that infuriated her daughter. “How can you stand it, Mom?” Anne would demand. “It’s not right. It’s totally unfair. You should stand up and do something about it.”
Not that Toot could ever be described as a shrinking violet. “I was afraid of her,” said Alton Kuioka, who was a young trainee in the Bank of Hawaii’s loan department in 1969. Kuioka would eventually become the bank’s vice chairman. “She definitely intimidated me. If you were new and learning she was like a drill sergeant.” Another trainee at the time, Dennis Ching, also confessed to being “totally scared” of Barack’s grandmother. “She was like the grande dame of escrow…. She gave me a file and said, “You’re a college grad. Here, close this.’ You don’t know how to swim, and she throws you in, and you either sink or swim.”
Barry was sensitive to the new dynamic in the Dunham household and to the simmering tensions between his grandparents. Fortunately for Barry, his mother left Lolo and returned with Maya to Honolulu, determined to pursue her master’s in anthropology at the University of Hawaii. Ann found a small apartment just off the Punahou campus and moved into it with her two children.
To all outward appearances, Punahou was not unlike any small New England college. There were arched windows, broad lawns, indoor and outdoor tennis courts, ivy-covered lecture halls of neo-Romanesque design, state-of-the-art laboratories, an Olympic-size pool, and—to maintain it all—a $180 million endowment. Barry would flourish here academically. “Barry could whip out a paper that was due the next day the night before,” recalled Suzanne Maurer, whose son, Darin, was a classmate of Barry’s. “The other kids spent weeks writing the same paper.”
Losing the baby fat that had made him the butt of jokes as a boy back in Jakarta, Barry became one of the lesser stars on Punahou’s basketball team—its sole left-handed player.
One of Barry’s closest friends at Punahou, Bobby Titcomb, remembered Barack “dribbling his ball, running down the sidewalk on Punahou Street to his apartment, passing the ball between his legs. I mean, he was into it.”
If he was not the most talented player, he was, said teammate Alan Lum, “a leader on the court” in part because of his penchant for enforcing the rules. “He would call people on it if they were doing something wrong,” Lum said. “He would question coaches. He was strong and confident enough to ask those questions. I respected him for that.”
Barack’s knack for “calling people out” did not make him any less popular with his fellow students. “He was the kind of guy,” said classmate Dan Hale, “who could walk into a room and navigate the cliques.” Although never regarded as a big man on campus, he made friends easily, went to school dances, and, like all adolescents, made his first few awkward attempts at dating. Weekends were spent bodysurfing at Sandy Beach in East Honolulu or picnicking at Puu Ualakaa State Park on Mount Tantalus, with its sweeping views of Diamond Head, Punchbowl Crater, and downtown Honolulu.
Occasionally, Barack would take off hiking with one of his friends. “We’d go hike up Peacock Flats and camp, just the two of us,” recalled Bobby Titcomb. “We’d try to get away from everything. We’d basically live on nuts and whatever we could eat on the trail for two or three days. And we’d talk
about how the world could be.”
Notwithstanding these periodic soul-searching treks into the wilderness à la Henry David Thoreau, Barack was never regarded as a loner. “He fit in as much as, if not more than, any other student,” Darin Maurer said. “He wasn’t the most popular kid in school, but he was certainly well liked. I never really saw that he was suffering.” Neither did Alan Lum. “To always have had that smile on his face…and yet to be going through that internal struggle,” Lum said. “I feel I lost an opportunity to connect with him.”
But Barry was suffering. Beginning with those first embarrassing questions from the other kids and their attempts to touch his hair or rub his head, Barry became increasingly sensitive to the fact that others viewed him as different. “I began to think,” he later conceded, “that as a black man being raised by white people, I should belong to both worlds—and yet I couldn’t help feeling that I really belonged to neither.”
In the small apartment he shared with his mother and sister, Barry watched Soul Train on television and sang along with the Temptations and Stevie Wonder—all a conscious effort, he would later admit, to shore up his sense of self as a young black American. His mother had always been his staunchest ally in that endeavor, but when Barry turned fourteen she made a stunning announcement: She was returning to Indonesia to do fieldwork for her PhD. She was taking Maya with her, but Barry would be allowed to decide for himself whether he was going to accompany his mother or remain in Hawaii.
Barry chose to stay behind with his grandparents. He had had enough of starting over. As difficult as it was being one of the few blacks at Punahou, he had made friends and was thriving academically. Moreover, Gramps and Toot had always stood by Barry while at the same time giving him considerable control over his own life—actually more autonomy than he had enjoyed while living with his mother. “We have total confidence,” they liked to tell him when he was faced with a decision, “that you will do the right thing.”
For Barry, the “right thing” meant confronting prejudice wherever it reared its ugly head. While growing up in the racial and ethnic hodgepodge that was Hawaii, Barry still encountered the kind of discrimination inflicted on blacks in less exotic locales. He demanded but never got an apology from a woman in the Dunhams’ apartment building who bolted out of the elevator when he stepped into it. At Punahou, Barry reacted to being called a “coon” by punching a classmate in the face. After he overheard a basketball coach dismiss members of an opposing team as just “a bunch of niggers,” Barry angrily informed the coach that he was “an ignorant white motherfucker.”
One of his closest friends at Punahou, Keith “Ray” Kakugawa, believed Barry was perhaps too sensitive to perceived slights. “He made everything look like it was all racial,” claimed Kakugawa, who was half black, half Japanese, and two years older than Barry. During one basketball game being coached by Kakugawa’s father, Barry complained that he was frequently benched just because he was black. “No, Barry, it’s not because you’re black,” the senior Kakugawa told him. “It’s because you missed two shots in a row.”
“Barry’s biggest struggles then,” Keith said, “were about missing his parents. His biggest struggles were his feelings of abandonment. That idea that his biggest struggle was race is bull.”
In truth, Barry did not have to venture outside his own family to encounter evidence of the barriers that still existed between blacks and whites. One morning, as she stood waiting for the bus that would take her to work, Toot was approached by a homeless man asking for money. She tried to ignore him, but the man persisted. So Toot dug around in her purse, pulled out a dollar bill, and, with a wan smile, gingerly handed it to him.
Toot had hoped the man would move on to the next victim, but instead he kept his outstretched hand palm-up and asked for more. He was, she later said, “insistent” and “menacing.” It was at this moment that the bus pulled up and Toot quickly hopped aboard. As she settled into her seat, she looked back at the homeless man. He never stopped smiling.
Now Toot wanted Stanley to give her a ride to work each morning. The idea of being accosted once again at the bus stop was too much for her. But Gramps knew the real reason behind his wife’s anxiety—which he shared with Barack—and he was anything but sympathetic. She would never say anything of the sort to her grandson, but Toot confided to her husband that the homeless man “was, well, you know…. He was black.”
The sudden realization that even his beloved grandmother harbored a deep-seated fear of black men pushed Barry over the edge. Toot and Gramps and his mother had always loved him unconditionally, and yet they did not have the answers he needed as a biracial man. He was growing up in a white household, and now, Keith Kakugawa said, Barry “felt he was not getting a part of who he was.”
Barry got some of the answers he needed from Frank Marshall Davis, a leading black activist and writer of the 1930s and 1940s who eventually settled in Hawaii. Gramps had introduced Davis to Barry in hopes that the older gentleman might give him some insight into what it meant to be a black American.
Barry would later write that he was “intrigued by old Frank, with his books and whiskey breath and the hint of hard-earned knowledge behind the hooded eyes.” When he told Frank about the panhandler who accosted Toot, Barry was surprised at the old man’s answer. Frank told him she was right to be scared because “black people have a reason to hate.” It was at that moment that Barry felt he might never have really known his family at all. “The earth shook under my feet…” he recalled. “I stopped, trying to steady myself, and knew for the first time that I was utterly alone.”
Barry continued his journey of self-discovery by plunging into the works of Langston Hughes, James Baldwin, W. E. B. Du Bois, and Ralph Ellison. When Barry checked The Autobiography of Malcolm X out of the Punahou school library, Kakugawa was taken aback. “Hold on, man,” he said. “What you gonna do? Change your name to something Muslim?”
“Well,” Barry replied with a shrug, “my name is Barack Obama.”
Kakugawa looked at his friend quizzically. “No it isn’t,” he insisted.
“Yes, my name is Barack. Actually, it’s Barack Hussein Obama.”
“Get off it!” Kakugawa shot back before the librarian threatened to throw them out.
What upset Kakugawa most was the fact that, for all his friend’s railing against racism, Barry “seemed about as solidly middle-class American as you can get,” he recalled. “I knew his dad was African and had taken off when Barry was small, but I had no idea that he had left Barry with an African name. I felt that he had obviously gone out of his way to hide that from me and from the rest of his buddies at the time.”
Indeed, Barry was not yet ready to fully embrace his African heritage by insisting that he be called Barack. But he did find a kindred spirit in assassinated Black Muslim leader Malcolm X, whose unambiguous hatred of “blue-eyed devils” softened after he visited Mecca and saw whites praying to Allah alongside blacks. Already exposed to its teachings during his four formative years in Indonesia, Barry now wondered if Islam did not provide an orderly framework for racial harmony—and a way for him to reconcile conflicts over his own biracial background.
Barry returned to the Koran for answers and told friends at the time that he was seriously considering joining the Nation of Islam. “For a while he talked a lot back then about what a great man Malcolm was,” Keith Kakugawa said. “But the rest of us were just interested in basketball and beer and sex, so he kind of gave up.”
Unable to reconcile his own growing resentment of “white folks” with his abiding affection for his white mother and grandparents, Barry stopped talking race altogether. “I learned,” he later explained of this period in his life, “not to care.”
Barry turned instead to alcohol—and to drugs. At sixteen, he began sneaking off to drink, smoke pot, or snort cocaine (“a little blow when you could afford it,” as Barry later put it) with his new friends. He financed his marijuana and cocaine purchases wit
h money he earned working summers at the Baskin-Robbins ice-cream parlor on Honolulu’s South King Street.
Despite the fact that he played on Punahou’s basketball team, he was not welcome at the Senior Bench, the stone bench where the jocks, cheerleaders, and other “popular” kids hung out. Nor did he spend time with the theater people, the nerds, or student-leader types like classmate Steve Case, who went on to cofound America Online.
“Barry hung out with the stoners,” said another classmate, who remembered that Obama was among the school’s fifteen or so “druggies.” Barry’s new group of friends were known to both faculty and students as the “Bingham Benchers” because they gathered each day on benches outside Punahou’s Bingham Hall (named after one of the first Christian missionaries in Hawaii, Hiram Bingham).
“Junkie. Pothead. That’s where I was headed,” Barry would later say, admitting that in high school he made plenty of “bad decisions.” There were several Bingham Benchers who paid a heavy price for those decisions. One was severely injured in a car crash while driving under the influence, one was committed to a mental institution after taking LSD, another barely survived an overdose, and yet another was arrested after police pulled him over and found drugs in the trunk of his car.
Keith Kakugawa’s plight may have hit closest to home. A track star with Olympic potential, Kakugawa slid into a life of drugs after graduation from Punahou and would wind up spending years behind bars.
Barry, who had wisely resisted the persistent efforts of one of his Bingham Bench buddies to get him to try heroin, somehow managed to emerge relatively unscathed. “You’ve been very lucky,” his mother said after confronting him about his unsavory band of pals. “But your luck won’t hold out forever. Don’t waste your life.”
Barry remained unconvinced. On more than one occasion, he drove drunk—speeding down a highway with gin clouding my head,” he recalled. There was, he would also admit, more than one occasion when he found himself bloodied in a booze-fueled fight. Through it all, there were the furtive meetings with drug dealers in public parks and alleyways—encounters during which he risked losing everything if one of those dealers turned out to be what he, like his friends, derisively called a “narc.”
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