soon as she was able, Sim Wenner freed herself entirely from motherhood by sending Jann’s sisters, Kate and Martha, away to boarding schools in Vermont and Colorado, respectively. The house on Rainbow Road was sold, and Ed Wenner moved to Southern California. Wenner would never forget his mother’s parting words: “You’re on your own, Buster Brown.”
•
“I WAS UNHAPPY,” Wenner wrote in an English paper about his first year at Chadwick School. “The year was miserable.”
But he had arrived at the right place. A way station for the progeny of the wealthy and famous from Bel-Air and Hollywood, Chadwick was a progressive private school on the Palos Verdes Peninsula, nestled like a bucolic camp at the top of a shady hill. Founded in 1935 by Margaret and Joseph Chadwick, it enrolled fewer than four hundred students, with only fifty-two in Wenner’s class. In his first year at Chadwick—or “Chadsuck,” as he called it—Jann Wenner spent weekends sitting in his dormitory watching TV alone, a picture of his mother on his desk, sulking over the divorce. Ed had a new girlfriend, a nurse from South Texas named Dorothy, who recalled meeting Jann in a garage in San Francisco that year: A straw hat on his head, no shoes on his feet, he looked to her like Huckleberry Finn. She told Ed that his son would be famous one day because he “had the courage to be different.”
For Wenner, Chadwick was, among other things, an education in celebrity. He was surrounded by the children of movie stars and famous directors: the offspring of actor Glenn Ford; the daughter of Jack Benny; the children of George Burns and Gracie Allen; and Yul Brynner’s son, Rock, with whom Wenner roomed in ninth grade. In a letter to his mother, Wenner described waltzing with Liza Minnelli at a school dance. “Are the movie stars’ kids the big shots in school?” she asked. “You sound impressed by them.”
He was—very. He later claimed Minnelli was his first girlfriend at Chadwick and that they held hands for a week. “I would go home with friends on the weekends, and that was always great, to stay at someone’s fabulous house in Beverly Hills,” recalled Wenner. “It was the first time I saw these extremely big, extravagant houses. I stayed at Dean Martin’s house; I was friends with the Martin girls.”
Chadwick was accepting in a way his own home wasn’t. He said being surrounded by wealth, and by Jews, made him feel more at ease. “I felt at home at last,” he said. “They became my family.”
With Wenner, there was a lot to accept. Bristling with insecurity, he regularly insulted the other students and teachers and gained a reputation as a prickly braggart. “He can be, and frequently is, extremely cruel to his classmates,” reported one teacher, “and his actions show an alarming lack of integrity.” His English instructor, Bill Holland, dubbed him Nox, for obnoxious, and the nickname stuck. “The obnoxiousness was very interesting,” said Wenner’s friend Bill Belding. “I originally attributed it to his being short, but looking back, it was his way of getting attention.”
Wenner was advised by school counselors to tamp down his attacks. “I was not Mr. Popular at that point,” said Wenner. “I didn’t become popular until the tenth grade when I decided to work on it.”
Wenner abused his teachers with impunity, starting with the adult head of his dormitory, a disciplinarian named John Simon. “Jann wanted to walk around barefooted; [Simon] wanted him to wear shoes,” said Dorothy Wenner, the woman Ed Wenner would eventually marry in the 1960s. “He refused. They had a battle going on all the time. Every time the phone rang, I was nervous. He was always in trouble.”
Once, Wenner cleaned his room to inspection standards but then hung closet hangers from the ceiling, claiming it was a piece of art inspired by the school’s own philosophy of “self-expression.” “It looked like a messy pile of shit in the middle of the room,” recalled Andy Harmon, son of Sidney Harmon, who produced the 1958 film God’s Little Acre. “And [Simon] got so angry, because everything was neat—the beds were made, we dusted, it was just ‘self-expression.’ Jann was going, ‘I’m going to fuck you so bad that you aren’t going to be able to retaliate.’ And that was the way his mind worked.” (For another infraction, Simon barred Wenner from going on the annual school ski trip, a stinging rebuke because Wenner considered himself the best skier in the school.)
But as people got to know him, they found Wenner strangely sophisticated for his age. Every morning he would open his box of Raisin Bran and count the number of raisins in the bowl, declaring the economy good or bad. “It was a revelation at that age, when I started school there, that one of my contemporaries could be that erudite and fascinating,” said Terryl Stacy, formerly Kirschke, who went to school with Wenner and later to Berkeley.
•
IN 1961, Sim Wenner published a dime-store novel called Daisy about a group of swingers (“The Club”) who lived in a Northern California suburb. “But one Saturday night they ran out of kicks—so someone jumped in the pool . . . with no clothes on,” went the copy on the back flap. “From then on things were different.”
The book was a thinly veiled roman à clef. The protagonist, Daisy, was the fill-in for Wenner’s mother. Philip, the character who stands in for his father, “worked long days and played long nights, and if another woman was more sympathetic than his wife, well, he just wanted someone to talk to.” Jann Wenner didn’t have to scratch very hard to see beneath the surface: Here were the neighborhood families from San Rafael, with whom the Wenners had evidently been having affairs, if the book was to be believed. In one scene, Daisy gets pregnant and tries to have an illegal abortion, a procedure she recounts in excruciating detail:
Soon she could feel the scraping inside of her and then chopping and she thought, Oh, my God, he’s cutting it up. He’s cutting up my baby! . . .
When Daisy starts bleeding profusely and is rushed to the hospital, the hapless husband believes she’s miscarried his baby, not someone else’s. In the very last sentence of the book, Daisy acts out her rage at Philip by raising a .22 rifle to his temple and pulling the trigger.
Wenner was horrified. After reading it, he wrote back to his mother, “The last paragraph was too much for me to bear psychologically. Your bitterness must be great, whether justifiable or not, but when so openly expressed as in the précis paragraph, you must have some idea of the effect on me.”
In reality, Sim Wenner did have an abortion before the divorce. As columnist Herb Caen wrote of Daisy in the Chronicle, “definitely not for baby unless yours has a different formula than most.”
After 1959, Wenner’s mother parented him almost entirely through letters, updating him on the family business, calculating his allowance and debts, correcting his grammar, suggesting books to read, and even upbraiding him for his souvenirs from a field trip to Mexico (“A bullwhip and a switchblade knife are the weapons of a [pachuco] not a gentleman”). Wenner, feeling orphaned, wrote “Bastard” on a letter. But even as she drifted away, she was intent on conscripting her children in battles against their father, who once sued Sim to reduce child support. It was an attitude Wenner slowly absorbed and would last for years to come. “She turned us against him, me and my sister,” Wenner said. “We didn’t realize it at the time, but it was a constant, steady stream of picking away, a slow character assassination.”
His sister Kate, after years of therapy, would maintain that Wenner and his sisters were deeply impacted by their mother’s bitterness and cruelty—a view Wenner only partly subscribed to. “I came around to her point of view about how crazy our mother was,” said Wenner. “My mother is, like, according to Katie, a classic narcissist.
“I escaped the impact of it,” he insisted. “I mean, I went off on my way, fairly young, and just had this enormous success, which just overwhelmed all the need to be introspective, all the need to be insecure, it just vanished.”
In eleventh grade, Wenner added an extra n to his own first name, making it Jann, inspired, he said, by a friend named Tedd. (His mother, a sometime fabulist, would tell a different story: Wenner was embarrassed when the school delivered his luggage to the girls’ dormitory, believing “Jan” was a girl.) Wenner tried out other names as well, once asking