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she had the same initials as Sim Wenner and buying her replicas of his mother’s clothes. Wenner was convinced he would marry Weigel once she graduated in 1964, a year after him. In Wenner’s yearbook, Weigel wrote in floral cursive, “I love you very deeply, I honestly do. With all my love, forever and ever.” (Margaret Chadwick congratulated Wenner on the yearbook but also advised, “Stop and think first my impulsive friend.”)

      When Wenner and Weigel returned to San Francisco for the summer, Weigel served as Wenner’s entrée to the small and provincial Bay Area society set, children of local industry and politics who mingled at lavish debutante balls. Wenner was enchanted by the Cotillion, the seasonal rite of house parties hosted by parents of young women and culminating in a grand ballroom party at the Sheraton-Palace Hotel in the winter. The swanning of the elite was closely monitored in the social pages of the Chronicle, complete with photo spreads and boldfaced captions, and Wenner read it religiously. “The wealth was on display, the booze, the big settings, young kids in black ties,” said Wenner. “I was just dazzled by it.”

      Wenner was a quick study, absorbing the backgrounds of the local gentry. There was Ned Topham from the Spreckels sugar fortune; James Pike Jr., son of the famous Episcopalian bishop and civil rights spokesman; John Warnecke, son of John Carl Warnecke, the architect of the Kennedy memorial. A few, like Richard Black, whose father worked for the California energy company PG&E, traveled in the same social orbit as the Hearst family, and Black’s stories of visiting the Hearst ranch in San Simeon were potent fuel for Wenner’s imagination.

      Meanwhile, Sim Wenner was living in Potrero Hill, at the time a largely black and industrial neighborhood that was becoming a bohemian enclave. After selling her share of the Baby Formulas business, she was socializing with a literary set at Berkeley, including beat writer Herbert Gold and artist and bullfighter Barnaby Conrad, and dating the Wenner family doctor, Sandor Burstein. Susie Weigel was fascinated by the unconventional divorcée but appalled by her lack of warmth for Jann. “She had three children and one bedroom,” said Weigel, later Susan Pasternak. “I was so upset for Jann because there was no place for the kids. And Jann wasn’t wanted by either [parent].”

      Weigel, who went on to become a Manhattan psychoanalyst, had a simple, powerful theory of her boyfriend’s psychology. “It was all about Sim Wenner,” she said. “There was no room for anybody else except her. I think Jann internalized that. The only way he was going to have room for himself was to create himself.”

      Through an acquaintance of Sim’s, Wenner was offered a job that summer as a traffic reporter at KNBR, the NBC affiliate, which required him to show up at 6:00 a.m. He didn’t like the hours so instead took a job as a day laborer on a construction site. He quit after a week—“I didn’t have the clothes for it,” he said—and accepted the NBC job. He fetched coffee, memorized the traffic jargon, and dubbed himself the Traffic Eagle around the bureau. Wenner spent his free time at the Weigel family’s retreat in Mill Valley, feeling at home with a Jewish family who had an “air of normalcy,” he said. Wenner impressed Weigel’s father, who told his daughter he believed Wenner would be famous, while Wenner labored to lose his virginity during secret make-out sessions with Susie in her bedroom. Weigel showed Wenner off to her friends, the brash young man with the oddly Swedish name and dashing grin who bragged a lot. They recognized the charm but also the grasping edge of his ambition. “When you’re on the inside where we were,” said Richard Black, “you can see faces pressed to the windows, and Jann was really determined.”

      Wenner opened a charge account at Brooks Brothers and had the pockets monogrammed on his button-down shirts, adopting the old-money look of William F. Buckley. That summer, Wenner bought a 1954 Jaguar XK120 for $120, hoping to fix it up himself and ferry his new friends around. When Weigel took him to pick it up, Wenner revved the engine and peeled off, leaving Weigel to frantically chase after him in her parents’ car. “He drove so fast,” she said. “So crazily fast. I was furious with him. It was so show-offy and made me so mad.” After that, Judge Weigel forbade her to drive with Wenner.

      The couple fought constantly. “He would annoy me to death,” said Weigel. Wenner enjoyed access to her family compound until her father discovered them making out to a Johnny Mathis record.

      In the fall of 1963, Wenner started classes at Berkeley, majoring in English literature with a minor in political science. A public school with twenty-six thousand students, Berkeley was a university at a crossroads. It was still an institution rooted in the 1950s, a factory producing graduates to plug into Eisenhower-era American capitalism. But a revolution was coming. In 1964, beatniks and Marxists were conspiring in local cafés to the sounds of Joan Baez and Bob Dylan while absorbing the literature of dissent from left-wing intellectuals like Eugene Burdick and Herbert Marcuse and North Beach cult heroes like Jack Kerouac and Lawrence Ferlinghetti. Wenner joined a student advocacy group called SLATE, run by two earnest young lefties named Phil and Joan Roos, who assigned Wenner to help edit student questionnaires for a tip sheet that rated professors called the Slate Supplement to the General Catalog. He took the most savage feedback from students and fashioned it into cheeky reviews tarring especially authoritarian professors. He remained an indifferent student—“it KEEPS ME OUT OF THE ARMY,” he told his grandmother—but he manicured his social life with great care, throwing parties for debutante girls and getting himself invited to the Sugar Bowl, a resort near the Nevada border that was a premier skiing destination for wealthy families. Joan Roos became Wenner’s surrogate mother, and he regularly showed up at her house for dinner and his favorite television program, The Man from U.N.C.L.E. Wenner became the associate editor of the Slate Supplement and bragged to the Rooses that he would one day be the head of NBC.

      Despite the far-left politics of SLATE, Wenner remained a stalwart establishmentarian. This was made clear the day President John F. Kennedy was assassinated in Dallas, November 22, 1963, news of which Wenner heard over loudspeakers coming from the student union at Berkeley. “This strange cry of agony went around, as if people were in pain and bodies being tortured,” he wrote of the moment. “I kind of slumped and bowed my head and cried.” When Barry Baron, a society friend Wenner met through Susie Weigel, showed up at Wenner’s apartment that evening, Wenner was conducting a private vigil, sitting cross-legged before two big candles, with tears in his eyes. “He took himself extremely seriously,” said Baron.

      Unlike Wenner, the SLATE crowd saw Kennedy as part of an imperialist conspiracy with ties to corrupt power. “The SLATE people were probably right, and had I been smarter, I would have agreed with them,” said Wenner. But Kennedy’s death, Wenner later said, was also the pivotal event that made the nascent counterculture possible.

      “It all wouldn’t have happened if Kennedy hadn’t got killed,” he told the British underground magazine Oz in 1969. “Everybody was still digging what was going on in that other scene. Kennedy made politics & the whole thing very relevant because he was young, he was attractive, he was just plain beautiful you know & not ugly.”

      •

      WENNER, like many young men, was focused on losing his virginity, though his reasons were more complex than some. He was troubled by his homosexual urges and thought that once he’d crossed that border, he’d be on the right path. When Susie Weigel came home for the holidays, she refused him sex. So Wenner pursued Weigel’s best friend, whom he considered the most “in” of the society crowd. Over the holidays, Weigel’s friend relieved Wenner of his outsider status. “I love you for what you have done for me,” he told her in a letter. “I hope you feel the same way.”

      She didn’t. After a weekend fending him off at the Sugar Bowl, she confessed the affair to Weigel, who was appalled and broke up with Wenner (and immediately took up with his best friend from Chadwick, Andy Harmon). Later, she saw Wenner crashing a deb party and was thoroughly disgusted. “I thought he was gross,” she said. “It was so obnoxious. I actually wanted nothing to do with him.”

      In his journals, Wenner admonished himself for pursuing Weigel’s friend, wondering what motivated him. “Is it her herself I want or is it what she represents?” he wrote. “There is something special, I can’t grasp it, about the SF society which I want.”

      Weigel, he wrote, had

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