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 faster 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