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  Obama later wrote that Keith possessed “a warmth and brash humor” that led to “an easy friendship,” but around Punahou, opinions on Kakugawa varied widely. Tony Peterson thought “his social skills weren’t the best,” and Pal Eldredge felt “he had a chip on his shoulder.” Keith’s longtime friend David Craven later commented that “Barry was the nice guy he hung around with,” but Keith’s best friend at Punahou, Marc Haine, remembered him as “a popular athlete, a popular figure.”

  To Kakugawa, fifteen-year-old Barry was “very, very quiet” and “very, very shy . . . I wouldn’t say introverted, but he was just a very shy, cautious kid.” Keith took a great liking to Stan Dunham. “Gramps was so great to all of us,” he recounted years later. “He was everyone’s grandfather.”

  Tenth grade was also the first time Barry played on an actual basketball team. Punahou’s junior varsity one was coached by 1961 Punahou graduate Norbie Mendez and played five preseason and fourteen regular season games between December 1976 and February 1977. Barry’s friends Mark Bendix, Greg Orme, Tom Topolinski, Joe Hansen, and Mark Heflin were also on the team. Obama never cracked the starting lineup, but he ended up as the third leading scorer as the team won nine of its fourteen official games.

  Yearbook photos that year show Barry with a bushy Afro and sometimes more than a little extra weight. A classroom picture captures a decidedly chubby Obama, whereas the ones for JV basketball and concert choir, perhaps taken later, show a visibly more mature fifteen-year-old. Sometime midyear Barry also spent significant time reading The Autobiography of Malcolm X. Keith Kakugawa remembers Obama pointing out the book in Punahou’s library, and Mark Hebing recalls Barry recommending it to him. Barry would later acknowledge absorbing the book that year, saying that Malcolm’s “repeated acts of self-creation spoke to me . . . forged through sheer force of will.”

  One Saturday evening sometime in the late spring of 1977, Kakugawa, Mike Ramos, a junior athlete on Punahou’s varsity basketball team, Obama, and fellow sophomore Greg Orme headed to a party at Schofield Barracks, a large U.S. Army base almost twenty-five miles northwest of Punahou. Most of Oahu’s African Americans were from military families, and the people at this party were predominantly black men and women several years older than the teenage Punahou quartet. Barry didn’t yet drink, but the group stopped to buy a case of Heineken on the way. Once there, the Punahou youngsters were not welcomed with open arms by everyone present.

  “The place was packed” and “it was dark,” Ramos remembered. He was more than a year older than Obama, and he was from a Filipino family of modest means; he had first met Barry a year earlier at a party where they discovered they were both fans of jazz saxophonist Grover Washington Jr. Orme was white, and he had known Obama since their seventh-grade year. Barry had passed along his interest in jazz to several friends that year. But at the Schofield party “everyone else, except the four of us, was dressed for a night at Studio 54, and we were dressed for a luau at the beach,” Kakugawa later said.

  Especially if they were haoles, Punahou students were looked upon “as the snobs, the rich kids” in many circles on Oahu. “Everyone on the island treated you differently once they knew you were from Punahou,” Keith said. Ramos remembers that Kakugawa, who was known to some of the people at the party, took offense whenever a verbal putdown of Punahou was uttered, and Ramos also remembered Keith “doing a bunch of trash talking” that night in response. Kakugawa admitted “we got in an argument because we were from Punahou,” and the four of them were headed for the door in less than an hour.

  Ramos was confused. “I was having a pretty good time”—“Why are we leaving?” For Orme, it was the first time he had been one of the few white people in a mostly black setting, and during the car ride back, he mentioned that to Barry. “One of us said that being the different guys in the room had awakened a little bit of empathy to what he must feel all the time at school,” Orme later recalled. Ramos agreed. “For the haole guys in our group, it was a kind of eye-opening experience for them.” But for whatever reason, Obama was upset by Orme’s comment—“he clearly didn’t appreciate that,” Greg remembered. Kakugawa thought Barry was bothered that one or more girls at the party had refused to dance with him, but Barry had been the youngest person there. Years later, he would describe the evening as a racial coming-of-age moment for him, but Ramos and especially Orme, who would become Obama’s closest friend during their two remaining years at Punahou, never heard or saw anything of the sort. Barry “would bring up worldly topics far beyond his years. But we never talked race.”

  In late April or early May 1977, not long after the party, Ann and Maya returned to Indonesia so that Ann could resume her dissertation fieldwork. Keith Kakugawa starkly remembers the day they departed. Ann told her son she was headed “home,” and “Barry was disgusted” after Ann and Maya were dropped off at the airport. “You know what, man? I’m really tired of this,’” Obama complained. Kakugawa told his friend that Ann was just doing her job, but Barry almost spat out his response: “Well, then, let her stay there and do it.” Keith’s buddy Jack McAdoo said he remembers that day too and recalls that “there was a lot of pain there” for Obama. Kakugawa knew that Barry “was going through a tough time” that spring and was experiencing a lot of “inner turmoil,” but “it wasn’t a race thing . . . Barry’s biggest struggles then were missing his parents. His biggest struggles were his feelings of abandonment. The idea that his biggest struggle was race is bullshit.” The crux of what his friend was wrestling with was “the hurt he felt about being abandoned by his mother” on top of his long-absent father.

  In later years, Obama would almost always suppress his past feelings about his by-then-deceased mother, but occasionally a highly revealing comment could slip out. “When I was a kid, I don’t remember having, I think, one birthday party the whole time I was growing up,” and he admitted, “I spent a childhood adrift.” But most of Barry’s classmates that spring were not aware of what Orme, Ramos, and especially Kakugawa could sense. “I was probably the only one who didn’t always see him smiling,” Keith recounted. To Kelli Furushima, an attractive Asian classmate whom Obama sought out at the once-per-class-cycle chapel sessions, Barry seemed “a happy guy, comfortable in his skin.” She enjoyed his “casually flirting” with her; “he was very friendly, very warm and had a great sense of humor.” When the school year was ending and everyone was signing each other’s 1977 yearbooks, Obama’s note on Kelli’s copy likewise reflected no angst: “Our relationship is still young so I am looking forward to picking it up where it left off next year. Your [sic] a small but dynamic person. Have a beautiful summer and see you next year. Love, Barry.”31

  Obama would not turn sixteen years old until August 4, 1977, so getting a summer job was a challenge, though years later he would say he had worked bagging groceries. But that birthday brought with it a driver’s license, and he began driving Stan’s reddish-brown Ford Granada, a car he would look back on with no fondness. One day that summer Keith Kakugawa and Marc Haine took Barry out paddling—Hawaiian for canoeing—and after they were back on dry land, beer was at hand. “I distinctly remember cajoling Barry into getting drunk with us.” He said, “I don’t drink,” but Keith corrected him: “You’re gonna drink.” Kakugawa boasted, “I was the one responsible for making Barry take his first drink, but Marc Haine was the one that handed it to him.”

  When Barry’s junior year began, a full-year course in American history was mandatory. Barry had the regular class, not the advanced placement version, taught by his classmate Kent Torrey’s father Bob, who knew Barry pretty well but remembers him as “a totally average” student. Another full year of English was required, but in addition to American Literature, the students chose from Punahou’s almost collegelike breadth of electives. With the standardized college-entry SAT exam scheduled for November, the fall kicked off with eight weeks or so of Saturday-morning preparation classes; instructor Bill Messer recalled Obama as “affable and ple
asant” but “oddly quiet in class.” Barry later claimed that “art history was one of my favorite subjects in high school,” but he also took drama. He and four classmates produced a short film they titled The Narc Squad, a parody of The Mod Squad. Linne Nickelsen, who had “long, straight blond hair and a closet full of miniskirts,” played the Peggy Lipton character, and Barry imitated the African American actor Clarence Williams III. Plenty of surfing footage was included, and Barry added a dashiki to his bushy Afro. Nickelsen later took credit for luring “Barry out of his dashiki for the pool party scene. . . . I must admit to being disappointed at not having received even passing credit for instigating that disrobing.” No screenings of the film have been reported for decades.

  Basketball season began in December. Barry and his closest buddies had been playing ball whenever and wherever possible, including evenings and weekends, sometimes going up against adult men and occasionally heading up to UH’s Manoa campus to play there. Outside of basketball season, Punahou’s mandatory after-school phys ed class was another venue for practicing “hack league” skills. Classmates and teachers all unanimously agreed that basketball was Barry’s real passion during all of his high school years, but that December Obama was relegated to the number-two, A-level varsity squad rather than making the cut for the top AA team. Greg Orme and Mark Bendix were also on the A team, but second-class status meant their practices were held every morning from 6:30 A.M. to 8:00 A.M. Once games got under way, the A ballers stumbled to an unmemorable record of seven wins and ten losses. A story in the student newspaper Ka Punahou asserted that the players were “having a good time” nonetheless. Coach Jim Iams insisted the season was “successful,” but decades later, Iams had no recollection of Obama being on his team.

  By the fall of his junior year, Barry was a more memorable member of another Punahou assemblage, known as the Choom Gang. It’s not clear when Obama first started to smoke cigarettes, but his friend Mark Hebing can picture Barry coming out of his grandparents’ apartment building on their way to go bodysurfing at Sandy Beach, east of Honolulu, carrying only a towel and a carton of cigarettes. Stan Dunham smoked three packs a day—“always Philip Morris,” his brother Ralph recalled—and Madelyn smoked even more. But the Choom Gang didn’t choom tobacco, they choomed pakalolo, the Hawaiian word for marijuana.

  Barry’s friend Mark Bendix was seen as “the ringleader” of the group. Tom “Topo” Topolinski, who was half-Polish, half-Chinese, explained that “everything centered around him. He always had the idea first, or he had a stronger opinion, or he wanted to do something rowdier. That was Bendix.” The other core members—Russ Cunningham, Joe Hansen, Kenji Salz, Mark “Hebs” Hebing, Greg Orme, Mike Ramos, and eventually Wayne Weightman and Rob Rask—enjoyed drinking beer, playing basketball, bodysurfing when the waves were up, and getting high whenever they had enough money. When they did, Bendix, Topo, and/or Barry would head over to Puck’s Alley on the east side of University Avenue where Ray Boyer, their go-to drug dealer, worked at Mama Mia’s pizzeria.

  Boyer was haole, but just as visibly, he was gay. “Let’s just say if he was closeted, he wasn’t fooling anybody,” Hebs said later. The Choom Gang called him “Gay Ray.” He was twenty-nine years old, and he lived in an abandoned bus inside a deserted warehouse in Kakaako, a then-desolate neighborhood west of Waikiki. Topo remembered that the scene there “was very scary. . . . No one in their right mind would live there.” Ray also had another main interest: porn. “I think he was looking to convert some people,” Topo said years later. “He would bring them back to his bus and stone ’em, with porn movies on—they were heterosexual porn movies, but it was still really creepy.” But Ray always had good-quality pakalolo on hand, so the connection was important. “Ray freaked me out. I was afraid of the guy,” Topolinski said. “But he did befriend us, and he was our connection . . . there were times where he would take us to a drive-in movie. . . . He partied with us, but there was something about him that never made me feel comfortable.”

  “We were potheads. We loved our beer,” Topo said, but the Choom Gang was not entirely about getting drunk or high. “We loved basketball so much that we couldn’t get enough of it,” and that was especially true of Barry. “For us, it was just all fun and games and basketball and hanging out, listening to music and going to the beach,” Topo emphasized. Bendix’s mother taught at Punahou, and they would quietly borrow her car on days when they had a break in their Academy schedules or when they simply decided to cut class. “We could have been easily terminated for what we did,” Topo said. “We did it all the time” since the lure of the beach oftentimes was too great. For most Choom Gangers, parental supervision was lax at best; when Topo’s parents discovered sand in his shorts one weekday and angrily confronted him about how their tuition payments were being wasted, his lesson was obvious: “I just learned to rinse my shorts out better.”

  Even for Topo, who had two parents at home, “the Choom Gang became more of a family to me than my own family.” For Barry, whose grandmother left for the bank each weekday morning at 6:30 and whose grandfather often was trying to sell life insurance in the evenings, his buddies and especially their devotion to basketball became the centerpiece of his daily life. His friend Bobby Titcomb, a year younger and not a Choom Ganger but whom one upperclassman called “a bit of a badass,” has vivid memories of “Obama dribbling his ball, running down the sidewalk on Punahou Street to his apartment, passing the ball between his legs. . . . He was into it.” Topo saw the exact same thing, with Barry “dribbling his basketball to class every day. He was married to that thing.”

  Mike Ramos’s younger brother Greg, who was a year behind Barry, and Greg’s best friend Keith Peterson shared the gang’s love of basketball and thought Obama was a visibly much happier teenager than most of his friends, including Mike, Greg Orme, Mark Bendix, and Joe Hansen. Keith was Tony Peterson’s younger brother, and by 1977–78 Keith and Barry were the only two black males in the Academy’s sixteen-hundred-plus student body. To Keith, Mike Ramos was “brooding, unpleasant . . . just mean.” From both Mike and Orme, Greg Ramos and Keith “got the full big brother to little brother treatment.” Orme was usually just “a jerk. Greg would challenge us to basketball games just for the pleasure of beating us to death.”

  Barry and Mike “were very close,” but Obama took part in none of the taunting the younger boys suffered from the older ones. Instead Barry manifested “a level of kindness and genuine caring” which “was pretty unusual, in particular with that group.” Hebs’s entire family felt the same way about how Obama treated Hebs’s younger brother Brad. Both Keith and Greg Ramos also felt that Topo and Bobby Titcomb were each “a great guy,” but they thought Obama “was always a happy guy.” Indeed, as Keith Peterson puts it, Barry “stands out in my mind as being the happiest of that group.”

  The Choom Gang had several regular off-campus hangouts—no one dared to choom at school. Each year’s catalog emphasized that Punahou “will not condone” drugs or alcohol and expressly prohibited even tobacco smoking “on or in the vicinity of” campus. Everyone understood that they would get expelled from school if they were caught. “We always gravitated to areas that were secluded,” Topo explained, and one of their favorite spots was a glade named the Makiki Pumping Station, near the Round Top Drive loop road that circles Mount Tantalus, just a bit northwest of Punahou. “It was a very tucked away, beautiful place,” Topo recalled. “It was kind of like our safe haven.”

  One evening the group headed up there in Mark Bendix’s Volkswagen van and Russ Cunningham’s Toyota. “We pulled over at the beginning of the hill and we puffed away,” Topo remembered. Then Mark and Russ decided their two vehicles should race. Barry and Kenji Salz were with Cunningham, Topo and Joe Hansen with Bendix. “‘On your mark, get set, go,’ so we took off, and we pulled ahead, and we made a turn, and then nothing happened. We’re up there, and we parked, rolled another fatty, and another one,” Topolinski said. “We’re not that much fast
er than them. Where the hell did they go?” So “we stayed up there for about twenty minutes and then we decided to go back down just to see what’s going on, and we’re about halfway down, and we see Barry running up the road, halfway in hysterics. ‘What the hell’s going on? Barry, where is everybody?’” Obama’s answer was startling: “‘Kooks rolled the car.’ ‘What do you mean he rolled the car?’ ‘It’s upside down in the middle of the road.’ ‘What?’ And he’s laughing. ‘Okay, well we need to go down there.’ So Barry got in the van, and we drove to the accident site and sure enough his little Toyota was on its roof in the middle of the road.”

  Cunningham had a bloody nose, but Kenji, like Barry, was fine. “We didn’t want to get in any more trouble so the rest of us left Russell there by himself,” Topo recalled, “and we piled in the van to go buy more beer.” After downing some, they decided, “Let’s go back up and see what’s up.” At the accident scene, “there’s fire trucks, flares,” even an ambulance. “We wanted no part of that,” so Bendix made a quick U-turn, and the Choom Gang headed for home.32

  Given the Choom Gang’s intake of both beer and pakololo, it was fortunate that nothing worse than a bloody nose and a totaled Toyota resulted from their many outings. In the middle of the 1977–78 school year, Ann Dunham and Maya returned to Honolulu, once again living at Alice Dewey’s home, so that Ann could take her doctoral candidacy exams in May. Lolo had been stricken with a serious liver disease, and Ann had taken the lead in forcing Union Oil to send him to Los Angeles for treatment before he then joined Ann and Maya at Dewey’s home to recuperate. It is unclear how much Ann saw of her son those months while he continued to live in his grandparents’ tiny apartment. Alice Dewey remembers Barry coming by one Sunday to take his mother, sister, and stepfather out for lunch. In late May, the three of them left to return to Indonesia, but no one recalls any intense bitterness like what Keith Kakugawa had witnessed when Ann left a year earlier.