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Isaac Davis Ripley, whose son would one day explore all corners of the earth, fled his dead-end Appalachian home at age fourteen and headed west. He didn’t get far before the Ohio River blocked his path. Unable to pay for a ferry crossing, Isaac swam solo across the turbulent river, eventually making his way to Northern California, seeking gold but instead finding work as a carpenter and cabinetmaker. By 1889, having settled in Santa Rosa, he fell in love with a woman fourteen years younger.
Lillie Belle Yocka’s family made their own risky journey toward dreams of a sunnier California life. The Yocka clan left Westport Landing (later called Kansas City) in the late 1860s, joining a straggly crowd along the Santa Fe Trail. During the westward journey, Lillie Belle was born in the back of a covered wagon, and she spent her childhood in a Northern California encampment on the banks of the Russian River.
On October 3, 1889, Lillie Belle—twenty-one and pregnant— married thirty-five-year-old Isaac Ripley, their union earning a brief mention in the Sonoma Democrat. Isaac built a cottage on a postage-stamp lot on Glenn Street, with intricate wood trim that looked like icicles.
A son arrived five months later, although the exact year and date of birth would remain a lingering mystery. Possibly to prevent profilers from revealing his mother’s premarital pregnancy, LeRoy Robert Ripley would never admit to being born on February 22, 1890; on passport applications and other documents he’d declare 1891, 1892, 1893, or 1894 as his birth year. He’d also later claim to have been born on Christmas Day or Christmas Eve.
Isaac and Lillie named him LeRoy but usually called him Roy. Only later in life would he adopt his middle name. A daughter, Ethel, arrived three years later and the family moved into a two-story bungalow Isaac built on Orchard Street, in a quiet grid of streets, home to saloon keepers and dentists, milliners and hops brokers.
LeRoy was lean and slight, socially timid but full of energy. He had a ball-shaped head and high forehead, a tousled mop of hair above comically jutted-out ears, a freckled and often-dirty face. His most notable feature was an unfortunate set of protruding and misaligned front teeth, a crooked jumble that practically tumbled from his mouth. When he smiled, it looked like he was wearing novelty teeth. He usually kept his mouth closed, lips stretched to hide his dental deformity.
He suffered from a debilitating shyness, caused largely by his disfigured smile, and by a stutter that filled his speech with uhs, ums, and frozen words. Ripley carried himself in ways meant to shield his smile and stutter from others: hunched inward, chin tucked down, shoulders drawn forward, a protective stance. He seemed fragile, almost effeminate, and years later would admit to feeling embarrassed about his “backwardness.”
Though thin, he grew to be fast and fit. A tireless neighborhood explorer, he ventured into the orchards north of town and probed south into the beckoning city. Mostly, he preferred to be alone. Barefoot, wearing carpenter’s overalls or knickerbocker pants and a ragged straw hat, the curious, dreamy boy roved and reconnoitered, collecting bottle caps, cigar bands, and the baseball cards that came inside cigarette packs. He amassed a set of nails bent in the shape of each letter of the alphabet, keeping them in a cigar box under his bed.
At the one-room Lewis School, he was forced to wear shoes. He owned a single beat-up pair and would stuff newspaper into the holes and gloss them over with shoe polish. Once, he actually made a pair of shoes from folded-up newspapers, tied together with string and caked black with polish. “He wasn’t fooling anyone,” said one classmate. When his clothes began to fray and tear, his mother crafted new outfits by recycling old dresses and leftovers from her laundry jobs. In his flower-print pants and shirts, LeRoy was cruelly mocked. Hey kid, why are you wearing a dress?
At lunchtime, while the other boys chased girls around the water pump and outhouse, Ripley sat beneath a tree, drawing pictures or reading books about pirates or explorers. In class, students were required to stand and recite poems or essays, but Ripley’s stutter made this an excruciating nightmare. Hunched over at his desk, he constantly scribbled and sketched in his notebooks. One teacher would smack him upside the head whenever she caught him copying scenes out of his history book instead of paying attention to the lessons.
“Everyone at school picked on him because he was so different,” a classmate would later say. “Not one of the guys,” said another.
After a bad day at school he’d escape to the attic of his house to draw or carve letters into the roof beams. Other early artistic inclinations included defacing his bedroom wall and chewing on pencils.
Though it would become an epicurean mecca, the land of Ripley’s youth—known by the Pomo and Miwok Indians as Sonoma, or Valley of the Moon—was more Wild West than wine country. A few years past its cowboy-and-Indian days, Santa Rosa and nearby Sonoma and Napa could be dangerous and deadly. When Ripley was a toddler, the Sonoma Democrat reported in breathless detail how Indians had looted a winery, adding: “The red-skins have been on a wild debauch.”
Also full of debauch were the newspapers. LeRoy learned to read in a lively two-paper town whose editors practiced what would soon be called yellow journalism. The Democrat and its rival, the Santa Rosa Republican, cackled with stories of murderous deeds and accidental deaths, divorces, suicides, and all variety of lunacy, a daily “news of the weird.” People plunged off railroad trestles, lost limbs beneath train wheels, became mangled by farm machines. They shot each other over card games, stole horses, robbed banks. The Democrat was especially poetic in its depictions of death, offering vivid descriptions of “putrescent” bodies “lying in pools of blood.”
Santa Rosa’s children were kept close to home and warned to stay away from the streets of downtown, especially Chinatown and its alleged opium dens. With his parents working—Dad as a carpenter, Mom taking in laundry and sewing jobs—Ripley had the freedom to ramble. A shoeless ragamuffin, he scampered through streets and alleys, avoiding the train and trolley traffic but irresistibly lured to Chinatown, where he’d peek into the laundries, restaurants, and shops. The proprietors, all men, puffed on long bamboo pipes and beckoned the curious kid, offering peculiar treats like lychee nuts.
Ripley found Santa Rosa’s small Chinese community exotic and bizarre. He was awed by the strange clothes, the spicy food smells, and the hand-lettered signs whose symbols looked like hieroglyphs. On the few occasions his parents took him to San Francisco, the highlight was always a brief glimpse of shambling Chinatown.
By 1900, Santa Rosa was home to six thousand farmers, timbermen, miners, vintners, and railroad workers—a vibrant downtown of dusty roads clotted by horse-drawn carts, bicycles, and livestock. The region had attracted a variegated mix of romantic eccentrics, including Thomas Lake Harris, charismatic leader of an alternative-lifestyle “Brotherhood of the New Life” commune, who extolled the virtues of wine, tobacco, and sexuality. As one Sonoma County historian put it, Santa Rosa and its environs was a land of “explorers, rancheros, vintners, artists, writers, athletes, movers & shakers & dreamers.”
Among the dreamers was famed horticulturalist Luther Burbank, who created hundreds of fruit, flower, and vegetable varieties at his agricultural laboratory—a thornless cactus, a white blackberry, a “New Seedling Cherry,” the result of grafting two hundred cherry varieties onto one tree. Burbank considered California an unconquered land, a new world where a man who avoided alcohol and tobacco “has ten thousand chances of success.”
Burbank’s prized creation, the perky perennial he named the Shasta Daisy, took seventeen years of trial and error.
The Santa Rosa of his childhood taught Ripley many things, not least of which was to appreciate off-kilter hobbyists, obsessives, and fanatics, the kind who would years later become targets of his own journalistic curiosity. Ripley’s hometown confirmed that you could be both odd and fascinating, obsessive and successful.
Even Ripley’s mother’s church had an appealingly curious backstory. In 1873, congregants of the First Baptist Church, having outgrown their place of worship, felled a 275-foot redwood; sawed and sliced it into studs, beams, and planks; hauled it to town; and assembled a new church from the single tree. Isaac Ripley had been among the builders of the structure that earned headlines as “The Church Built of One Tree.”
Evidence that a town of death and debauchery could also be a place of magic and wonder was found on the city’s stages, too. The Athenaeum Theatre hosted a unique medley of entertainment, from Shakespeare to vaudeville to minstrel shows. Newspaper ads hawked the “world’s greatest cornetist” and the “world’s most marvelous dancer.” The nearby Novelty Theatre hosted lowlier acts: a midget show, a bone-playing musician, a boxing kangaroo.
Santa Rosa was also a regular stop on the circus circuit, visited by Tom Thumb’s “Smallest Human Beings in the World” and Buffalo Bill’s “Wild West Show.” The Ringling Brothers Circus visited annually, and when Barnum & Bailey’s “Greatest Show on Earth” arrived in town, the Democrat described its “troupe of wonderful midgets [and] a giant who stands nearly eight feet tall—All these curious people . . . living wonders.”
For a kid who was mocked and teased for his funny looks and shabby clothes, his balky speech and his pathological dread of girls, Santa Rosa proved to be an ideal hometown, a place where the unusual was acceptable, where a person could be a bit peculiar and still succeed.
“Anybody who is born in Santa Rosa must turn out to be either an artist or a poet, for the spirit of the hills gets into your blood out there,” Ripley would say years later, calling his home “the quaintest little town in the United States.”
By the fall of 1904, when he entered Santa Rosa High, Ripley had grown taller and stronger, filling out his scrawny frame and showing signs of athletic prowess. In the spring of his freshman year he joined the baseball team, though he remained an awkward, eye-averting doodler. “No one thought he would amount to much of anything,” said a classmate.
In the presence of female classmates, he showed a laughable insecurity. Teachers recalled seeing him run when girls came near and classmates would later remember him as “not much of a ladies’ man.” His one true female friend, who had roamed with him through downtown and among Chinatown’s alleys, was Nell “Nellie Bell” Griffith. By high school, Nell had grown into a dark-haired beauty, a poet and basketball standout. Though she’d tell classmates that she and LeRoy were just “very close friends,” Ripley clearly thought it was more than that.
Nell never seemed bothered by Ripley’s gawky looks. She knew he was “awkward,” but also funny, smart, and artistic. Nell’s parents owned an orchard, where she and Ripley often played among the rows of trees. Ripley once upset a bees’ nest and ran away screaming—a scene that he captured in a pencil drawing, which he presented to Nell.
In class, Ripley began letting classmates lean over his shoulder to watch him draw amusing caricatures of peers and teachers. Among his popular sketches were those of the balding, bespectacled history teacher, Charles T. Conger, despised by students and teachers alike, whom Ripley posed in what he called “some of his favorite attitudes”: sitting at his desk with arms spread wide; sitting on a stool pointing a long ruler at the blackboard. Conger didn’t appreciate the likenesses, but others did, and classmates’ reactions to his drawings marked the first time Ripley stood out for reasons other than his crooked teeth and stammer.
Notebooks, textbooks, sheets of scrap paper—no empty space was safe from Ripley’s eager pencil. His happiest, purest school moments were with a pencil in his right hand, a clean white space before him. His family couldn’t afford art supplies, so he hoarded butcher paper and used a cutting board as an easel. Though he never took drawing lessons, he practiced relentlessly, sitting in front of a mirror to study his own lips, eyes, and facial muscles, then drawing his own expressions on crumpled scraps of butcher paper, smiling, scowling, frowning.
He once splurged on a five-cent postcard featuring a painting called The Wedding Feast, and practiced copying the scene, over and over. He would follow his sister and mother around, sketching them as they cleaned dishes, washed clothes, or hung laundry, pleading with Ethel or Lillie Belle to sit or stand still for just a few minutes. “Pose for me just a little while, will you?” he’d ask, and they usually gave in.
As he prepared to enter his second year of high school, in mid-1905, Ripley seemed to be settling into a comfortable routine. He’d started making a few friends, and had begun making a less-than-negative impression on classmates. The bucktoothed young misfit was beginning to feel normal.
That’s when everything changed.
Isaac Ripley was a glum, gruff, and serious man, judging by the scant few surviving photographs: the corners of his mustachioed mouth were pulled low and his deep, dark eyes were typically pinched into a scowl. He must have seemed especially forlorn that Friday night in September of 1905.
Ripley’s grandmother, who had recently moved to Santa Rosa, had died of a lung hemorrhage that summer, and Isaac was still mourning his mother’s death. After dinner on the night of September 15, he felt a crushing pain in his chest. Lillie Belle summoned the local physician, Dr. Jesse, who gave Isaac some medicine to ease his discomfort. A few hours later, just before midnight, Isaac was beset by another attack. Within thirty minutes he was dead, his wife and children by his side.
Ten days shy of his fifty-first birthday, Isaac was buried at the Odd Fellows Cemetery, just blocks from his home. A choral quartet sang as Isaac’s brethren from the carpenters’ union and the Woodmen of the World lowered his casket into the ground. LeRoy and sister, Ethel, stood beside their mother, who held in her arms the newest family member, sixteen-month-old Douglas.
Alone with three children, Lillie had no apparent skills with which to find a decent job. She began renting out a room to tenants, baking bread, continuing to take on needlework and the laundry of others while looking for a nursing job. Somehow, she was determined to keep her fragile household intact.
Short, tough, and attractive, she had always been the dominant parent, quick-witted and sharp-tongued. With a pouty mouth, dark skin and eyes, narrow waist, and shapely hips, even Ripley’s classmates thought his mother was “quite attractive.” Though he’d later speak adoringly of Lillie, Ripley “never spoke much about his father,” according to one longtime friend. “And the impression is left, somehow, that he did not think too much of him.”