Sim would describe the birth of her son as a time of intense loneliness: The bars on the hospital windows, she told Wenner in 1982, were all that kept them both alive. “I would have jumped,” she said. Wenner’s first pediatrician was Dr. Benjamin Spock, the progressive doctor and civil rights activist, who published the best-selling Common Sense Book of Baby and Child Care the same year Wenner was born. Sim, whose name was shorthand for her maiden name, Simmons, came from a well-off family who lived on the Upper West Side near Central Park. Her parents were first cousins. Sim’s mother, Zillah, came to New York from Australia, where her parents were unsuccessful merchants. Sim’s father, Maurice Simmons, grew up poor in New York, but he shone with ambition: After graduating from City College in Manhattan, he served in the army during the Spanish-American War and helped found the Jewish War Veterans of the United States of America. He became a judge in New York and gave the nominating speech for Al Smith’s first run for office in the early twentieth century. Zillah, whom he married in 1919, ran an antiques store that sold silverware.
The Simmonses poured their immigrant hopes into their firstborn son, Robert, but the birth of their second child, a daughter, two years later, would mark the abrupt end of the marriage. A serial philanderer, Maurice had an affair with the family governess in a drama that actually made headlines: The New York Times reported that Zillah filed for divorce, the governess was arrested for physically attacking Zillah with a dog leash, and Maurice sued Zillah’s sister-in-law for libel after she called him a “scoundrel.” By the time Sim was born in 1922, Zillah was so bitter she couldn’t bring herself to name her daughter. “She was ‘baby girl something’ for the longest time,” said Wenner.
Sim’s childhood was shadowed by Zillah’s anger—her mother regularly threatened to throw herself out the window—and starting at age twelve, Sim was raised by her maternal grandmother, Kate Gilbert Symonds, with whom she often shared a bed. By the time she reached adolescence, Sim had developed a flinty independence and a desperation to escape her mother. Around 1940, a white knight presented himself: Edward Weiner, a stocky but sporting fellow she met on a ski trip to Stowe, Vermont.
Ed was raised by a single mother who immigrated to Boston from Russia with a penniless and ne’er-do-well husband. After Ed’s father died of cirrhosis when Ed was five, he and his mother, Mary, and an older sister made their way to Brooklyn, where Mary changed the family name to Weiner to escape her past (the previous name was forgotten, as was her husband’s name). Mary Weiner struggled with a lingerie business and tasked little Edward with helping women snap on their brassieres. Ed spent hours alone in the library, educating himself enough to start high school at thirteen. He came to hate his mother for reasons he couldn’t discuss: He had watched her and his sister spread newspapers around the shop and burn their business down to collect the insurance money—an act that nearly killed the Italian fruit vendors who lived upstairs. As he would recall later, he and his mother stood on the street and watched it burn: “The fruit merchant came out and he said, ‘You did this! You did this! You could have killed my baby!’ ”
His mother fainted. “After the fire,” Ed later said, “the Italian family moved out and she used the insurance money to expand and buy new merchandise.”
Though he spent years in denial, the event left Ed tortured with guilt. “I could have killed somebody,” he confessed in a documentary made by Jann Wenner’s sister Kate. “You don’t know what that feels like.”
“Cheating, lying—I thought that’s the way life was,” he admitted. “How could I be something people respected or admired? I’m going to be something that people will like. I’m going to make myself something.”
One day, Ed stole money from his mother’s cash register, she discovered it, they fought, he struck her, and she had him arrested. After a night in jail, Ed left home and never returned. “No matter what I did, I had to do something bigger, tougher, to prove myself,” he said. “I had to compensate for being poor and growing up in the slums.”
At the dawn of America’s entrance into World War II, Ed’s ambition was the antidote for Sim’s desperation. After Ed enlisted in the air force, Sim joined a women’s volunteer unit. And while on spring break from Hunter College, she flew to Alabama, where Ed was stationed, and they got married in an air base chapel in the spring of 1941.
At first, the couple lived apart. Sim was training as a supply officer at Radcliffe College in Cambridge when she discovered what she would call her “homosexual gene,” having an affair with a fellow volunteer. The woman, nicknamed Smitty, asked Sim to run away with her to California. Sim confessed the affair to Ed, who was surprisingly understanding and offered to end the marriage. But Sim would say she wanted a “normal” life with children—not one living as a lesbian pariah—and went with Ed. To cement the decision, they decided to have a baby. In the spring of 1945, while Sim and Ed were furloughed in New York, they conceived Jann Wenner on a train trip to Chicago. After he was discharged from the air force, Ed became a traveling salesman of surplus mattresses for recycling into paper mulch. With Jan Simon Wenner in utero, they moved to Elmhurst, Queens.
Ed and Sim rejected Judaism, viewing the old-world culture as an embarrassing millstone. In Wenner’s baby book, Sim wrote that “any religious ceremonies will be of his own choosing and not ours.” For Ed Wenner, “the words ‘Jew’ and ‘poor’ were synonymous,” Kate Wenner wrote in Setting Fires, a loose fictionalization of their father’s history published in 2000. If they were going to reinvent themselves, they had to get away. Around the time Jann was born, Ed and Sim changed the family name to Wenner from Weiner. “The explanation was that he didn’t want us as children teased,” said Jann Wenner. But it also obscured the Jewish background that Ed resented.
In 1946, Ed dreamed up a business idea, inspired by a story he’d read in a magazine: The babies of British war brides, while on boats to America, had gotten sick from drinking unsterilized milk. “It hit me right then,” Ed told Newsweek in 1961, “terminal sterilization had possibilities as a commercial venture.” So in 1947, they put Jann Wenner in the back of their Dodge Coupe and drove west, part of a great postwar migration to California. “Of course,” wrote Sim Wenner in a memoir published in 1960, “that’s where any real pioneer headed in those days. It was the land of gold, a state littered with patio pools and producing parents.”
After a period in the city, they settled north of San Francisco in Mill Valley, just over the Golden Gate Bridge, and Ed Wenner rented a former butcher’s shop with a freezer, spending nights in a sleeping bag while he figured out how to sterilize and bottle formula. To sell the idea, he peddled a twenty-five-page “Mother’s Guide” describing the benefits of formula but then shifted to bulk sales to Bay Area hospitals. Despite her skepticism, Sim’s mother, Zillah, lent them money to expand, and Ed bought a green truck, had a stork stenciled on it, and began delivering formula.
The business boomed, and so did the Wenners. Sim became pregnant again not long after they moved to California and gave birth to Kate Wenner in 1947. Two years later, she had another girl, Martha. But as Ed became consumed with the business, Sim began to think of motherhood as both too much and not enough. When Jann Wenner was two, she began going to work as the office manager for Baby Formulas, leaving the kids at home with a series of African American nannies. Sim Wenner later maintained that her motherly remove made her son independent. He could scramble an egg when he was three years old, she claimed.
However it happened, what nobody could deny was that Jann Wenner was precocious in the extreme. Short and pudgy, with a prickly intelligence and a bracing self-confidence, he was kicked out of nearly every school he attended until the age of eleven. “A pain in the ass,” his father said. He could be unpredictable and cruel. In third grade, he physically attacked the principal of his public school. A year-end review by his teacher characterized eight-year-old Jann as unusually intelligent but with a compulsion to violence. “In group situations he tries to dominate,” his teacher wrote, “withdrawing when the group does not recognize his leadership. He attempts to make