When Donald was born, less than a year after World War II ended, Fred and Mary Trump and their four children lived in a two-story Tudor revival on Wareham Place, a couple of blocks from Grand Central Parkway, a major commuter thoroughfare. But when a fifth child, Robert, was on the way, Fred bought two adjoining lots across the backyard and built a twenty-three-room manse on Midland Parkway. It looked like a faux Southern plantation. Seventeen brick steps led up a sloping hill to the front door, which was framed by a colonial-style portico, a stained-glass crest, and six imposing white columns. The house was the talk of the neighborhood of lawyers, doctors, and business executives, if not for its size than for Fred Trump’s apparent wealth, as suggested by the navy-blue Cadillac limousine in the driveway, with a license plate boasting his initials, FCT.
The Trumps had other things hardly anyone else possessed, including a chauffeur, a cook, an intercom system, a color television, and a sprawling electric train set that was the envy of the neighborhood. Later, while his pals were riding Schwinn bikes, Donald would cruise on a ten-speed Italian racer. But wealth was not all that set the Trumps apart. When Fred Trump asked if he could put a television antenna on a nearby house, thinking its higher elevation would improve his signal, the neighbor, Chava Ben-Amos, agreed. But when Fred told her she could not use the antenna for her own television, Ben-Amos told him the deal was off.
Fred Trump’s children apparently inherited their father’s chilly attitude toward the neighbors. When a neighbor’s ball accidentally bounced into the Trumps’ spacious backyard, young Donald growled, “I’m going to tell my dad; I’m going to call the police.” Another neighbor, Dennis Burnham, grew up a few doors away from the Trumps. When he was a toddler, his mother placed him in a backyard playpen. Once, after going inside for a few minutes, she returned to find that little Donald—five or six at the time—had wandered over and was throwing rocks at her son, Burnham said. Donald’s fearlessness impressed his sometime babysitter Frank Briggs. As afternoon turned to dusk one day, Briggs led Donald into a sewer that was under construction in Forest Hills. They remained belowground for two hours. “All of a sudden, it was pitch-black and you couldn’t see the entrance or anything,” Briggs recalled. “And the thing that amazed me was that Donny wasn’t scared. He just kept walking.”
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WHEN DONALD WAS READY for kindergarten, the Trumps sent him to the private Kew-Forest School, where they had enrolled his older brother, Fred Jr., a fun-loving boy who dreamed of becoming a pilot. Donald’s two older sisters, Maryanne, who had her father’s drive, and Elizabeth, sunny like her mother, also went to Kew-Forest. In high school, Maryanne, who would grow up to be a lawyer and a federal judge, emerged as the family’s academic star. She joined Kew-Forest’s debating team and student council and wrote poetry, including a maudlin riff entitled “Alone,” which was published in the school yearbook: “On the familiar school grounds, where groups of boys and girls stop to chat, laugh and then move on to see their other friends, she stands disregarded by all. She, alone and friendless, cannot even hope to join their happy crowd as they walk toward the corner candy store.”
Donald spent the most time with Robert, his little brother, a quiet, sensitive youngster and easy prey for an aggressive older sibling. As an adult, Donald liked to tell the story of when he appropriated Robert’s building blocks for his own and glued them together because he was so pleased with what he had made. “And that was the end of Robert’s blocks,” Donald recalled.
At Kew-Forest, Donald encountered a dress code—ties and jackets for boys, skirts for girls—and a strict set of rules, including the requirement that students rise at their desks when a teacher entered the classroom. From the start, Donald and his friends resisted their teachers’ commands, disrupting class with wisecracks and unruly behavior. “We threw spitballs and we played racing chairs with our desks, crashing them into other desks,” recalled Paul Onish. Donald spent enough time in detention that his friends nicknamed the punishment DTs—short for “Donny Trumps.”
Their classmates did not always appreciate their antics. In second grade, after Trump yanked her pigtails, Sharon Mazzarella raised her metal lunch box in the air and brought it down with a clunk on Donald’s head. No matter the consequences, Donald’s behavior did not change. “He was headstrong and determined,” said Ann Trees, a Kew-Forest teacher who monitored students in the cafeteria. “He would sit with his arms folded, with this look on his face—I use the word surly—almost daring you to say one thing or another that wouldn’t settle with him.” Steven Nachtigall, who lived a couple of blocks away from the Trumps in Jamaica Estates, said his own impression of Donald was cemented when he saw him jump off his bike one afternoon and pummel another boy. “It’s kind of like a little video snippet that remains in my brain because I think it was so unusual and terrifying at that age,” Nachtigall would say six decades later.
By his own account, Trump’s primary focus in elementary school was “creating mischief because, for some reason, I liked to stir things up and I liked to test people. . . . It wasn’t malicious so much as it was aggressive.” As a second-grader, as Trump has described it, he punched his music teacher, giving him a “black eye” because “I didn’t think he knew anything about music, and I almost got expelled. I’m not proud of that, but it’s clear evidence that even early on I had a tendency to stand up and make my opinions known in a very forceful way.” Peter Brant, his best friend at Kew-Forest, is among several of Donald’s pals who recall neither the incident nor Trump’s ever mentioning it. When Trump was asked again about the incident decades later, he said, “When I say ‘punch,’ when you’re that age, nobody punches very hard. But I was very rambunctious in school.”
The teacher, Charles Walker, who died in 2015, never told anyone in his family about a student’s striking him. Yet Walker’s contempt for Donald was clear. “He was a pain,” Walker once said. “There are certain kids that need attention all the time. He was one of those.” Just before his death, as he lay in bed in a hospice, Walker heard reports that Trump was considering a run for the presidency. “When that kid was ten,” Walker told family members, “even then he was a little shit.”
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TRUMP’S GRADES SUFFERED AND his behavior got him in hot water, but he found success in the gymnasium and on the ball field, where his athletic prowess was unmistakable. In dodgeball, Donald was known for jumping straight up in the air and pulling his knees up to avoid being struck. “The Trumpet was always the last man standing,” remembered Chrisman Scherf, a classmate, invoking his old nickname for Donald. Donald and his buddies played punchball and basketball, football and soccer. But his favorite sport was baseball, which inspired him to write an almost Zen-like ditty that was published in the school yearbook:
I like to see a baseball hit and the fielder catch it in his mitt. . . . When the score is 5–5, I feel like I could cry. And when they get another run, I feel like I could die. Then the catcher makes an error, not a bit like Yogi Berra. The game is over and we say tomorrow is another day. —Donald Trump
In the mid-1950s, New York City was America’s undisputed baseball mecca, with the Yankees in the Bronx, the Dodgers in Brooklyn, and the Giants in upper Manhattan. On a fall afternoon in 1956, when he was ten, Donald lined up with fellow Kew-Forest students outside the school to wave at President Eisenhower as he passed by in a Chrysler Imperial limousine taking him to throw out the ceremonial first pitch at the Yankee-Dodger World Series. Donald’s favorite players were Yogi Berra of the Yanks and Roy Campanella of the Dodgers, both catchers whose championship heroics Donald followed by sneaking a transistor radio into class, the wire of an earplug concealed beneath his shirtsleeve.
By sixth grade, Donald’s ability as a right-handed hitter was fearsome enough that opponents shifted toward left field to defend against him. “If he had hit the ball to right, he could’ve had a home run because there was no one there,” said Nicholas Kass, who was a couple of years older. “
But he always wanted to hit the ball through people. He wanted to overpower them.” When he played catcher, his favorite position, Trump’s uniform was the dirtiest on the field. He shrugged off foul balls that clanged against his mask and used his big frame to block errant pitches. “He was fearless,” Peter Brant recalled. “If he stole a base, he came in all guns a-blazing.” He did not like to fail, as his neighbor Jeff Bier discovered when Donald borrowed Bier’s favorite bat and made an out. Frustrated, Donald smashed the bat on the cement and cracked the timber. He was too lost in his fury to apologize.
In those years, young ballplayers wanted the new, webbed fielders’ mitts that Rawlings was beginning to make. Peter convinced his father to buy him one for $30, as long as the youngster earned $15 doing chores around the house. But Donald could not persuade Fred Trump that the more modern glove was worth the price. Fred bought his son a cheaper model.
For all his wealth, Fred did not want to spoil his children, encouraging them to earn money by collecting empty White Rock soda bottles and turning them in for the nickel deposit, and by delivering newspapers (when it rained, he’d drive them on their routes in his Cadillac). A workaholic, Fred would take Donald with him to construction sites and to his headquarters, a converted dentist’s office near Coney Island, where the boy would absorb his father’s attention to detail and obsession with cutting costs. At Kew-Forest, where Fred served on the board of trustees, he complained that the school was wasting funds by adding bathrooms for the new gymnasium. The school already had enough toilets, he groused. On his own projects, Fred would pick unused nails off the floor and return them to his carpenters. He saved money on floor cleanser by ordering lab analyses of store-bought products, buying the ingredients, and having them mixed to produce his own.
A fastidious, formal man who wore a jacket and tie even at home, Fred could be dour and socially awkward. His wife, Mary, relished attention, thrusting herself to the center of parties and social gatherings. She also loved pomp, sitting for hours to watch the coronation of Queen Elizabeth. A homemaker, Mary devoted herself to charitable work and volunteering at Jamaica Hospital, where Donald was born. Mary had various medical problems, including a hemorrhage after Robert’s birth that required an emergency hysterectomy. From his mother, Donald inherited a wariness about catching germs that led to years as an adult when he avoided shaking hands.
Fred and Mary Trump ran a disciplined household, forbidding their children to call each other by nicknames, wear lipstick, or go to bed past their curfew. The Trumps questioned their children each night about their homework and demanded that they perform their chores. Just as he did at school, Donald rebelled against the rules, arguing with his father. Nonetheless, Fred always told his son that he was a “king” and that he needed to become a “killer” in anything he did.
Hungry for a sense of autonomy, Donald and his friend Peter created a routine that they kept secret from their parents. On Saturday mornings, after playing soccer at school, they put on their pressed chinos and dress shirts and walked to the Union Turnpike subway station, where they boarded the train for Manhattan. The city was far more exciting and enticing than the quiet, orderly streets that defined deep Queens, a feeling that would not dissipate as they approached adulthood. Wandering the city, the boys fancied themselves urban Davy Crocketts, exploring Central Park’s bucolic expanse, watching black men play pickup basketball on outdoor courts along the East River, observing panhandlers in Times Square, eating hot dogs bought from street vendors, and hopping on stools at a diner to drink egg creams. At their favorite novelty shops in Times Square, the boys were drawn to the selection of switchblades. On Broadway, West Side Story was a smash hit, and Donald and Peter, imagining themselves gang members on the city’s mean streets, bought knives to fit the part. Back in Queens, the boys played a game they called Land, in which they flung their knives at the ground and then stepped on the spot where the blade had pierced the dirt. At first, the knives they used were six inches long, but they graduated to eleven-inch blades as they became more daring. (Trump denied ever being “a knife person. . . . I never had a switchblade in my life. That’s crazy.”)
Near the end of seventh grade, Fred discovered Donald’s cache of knives. Fred called Peter’s father, who found his own son’s collection. The parents were infuriated to learn about the youngsters’ trips to the city. As an adult, Peter Brant would see those adventures as an early sign of independence and ambition, a drive that would propel both men to fame and vast wealth. (Brant became a paper-industry magnate, publisher, and movie producer.) But Fred Trump, alarmed by how his son was evolving, decided Donald needed a radical change.
In the months before eighth grade was to begin, Donald seemed to vanish. Peter heard from a friend that his buddy would be attending another school. When Peter telephoned him, Donald, his voice thick with dejection, said that his father was sending him to New York Military Academy, a strict boarding school seventy-five miles north of Queens. Peter was stunned. His best friend was being sent away, and for reasons that seemed, at least to a thirteen-year-old, almost inexplicable.
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DONALD ARRIVED AT NEW York Military Academy in September of 1959, a stocky teenager bewildered by his new surroundings. An hour north of Manhattan, the school was located in tiny Cornwall-on-Hudson, on a campus with a culture so strict and unforgiving that one desperate cadet was rumored to have jumped into the Hudson River to swim to freedom. Instead of the delicious steaks and hamburgers served by the Trump family cook back home, Donald had to sit in a mess hall alongside fellow cadets and fill his plate from vats of meat loaf, macaroni and cheese, and something the students called “mystery mountain,” a concoction of leftovers that were deep-fried and shaped into balls. Instead of his own room in a vast mansion, he slept in a barracks, awakened each morning before dawn by a recording of a bugle playing “Reveille.” Instead of having his own bathroom, he had to stand beneath an oversize showerhead and bathe with other boys. Instead of adhering to his father’s commands, Donald had a new master, a gruff, barrel-chested combat veteran named Theodore Dobias.
Dobias, or Doby as he was known, had served in World War II and had seen Mussolini’s dead body hanging by a rope. As the freshman-football coach and tactical-training instructor, Doby smacked students with an open hand if they ignored his instructions. Two afternoons a week, he would set up a boxing ring and order cadets with poor grades and those who had disciplinary problems to fight each other, whether they wanted to or not. “He could be a fucking prick,” Trump once recalled. “He absolutely would rough you up. You had to learn to survive.” To glare at Doby, or suggest the slightest sarcasm, Trump said, caused the drill sergeant to come “after me like you wouldn’t believe.”
Whether his students were the sons of plumbers or millionaires, Dobias did not care. They would follow his orders, no questions or whining tolerated. Donald was no exception. “At the beginning, he didn’t like the idea of being told what to do, like make your bed, shine your shoes, brush your teeth, clean the sink, do your homework, all that stuff that a kid has to do when you’re a cadet at an academy of four hundred kids,” Dobias said. “We really didn’t care whether he came from Rockefeller Center or whatever. He was just another name, another cadet, just like everybody else.”
Founded in 1889 by a Civil War veteran in what had been a summer resort hotel, the academy modeled its strict code of conduct and turreted academic building after West Point, located five miles south along the Hudson. About 450 students were enrolled, all of them white except for a couple of dozen Latin Americans. The school did not admit blacks until Donald’s senior year. Women would not arrive for another decade. The military academy was a place where, as the school’s slogan put it, the boys were “set apart for excellence”; the idea was to inject discipline and direction into boys who arrived on campus unformed and untamed. That involved breaking them down to build them up. Every student received a blue booklet titled “General Order No. 6,” which laid out th
e punishments for a variety of infractions. A dirty uniform, unpolished shoes, uncut hair, an unmade bed, “not walking properly,” “holding hands with a young lady,” and nudity in the barracks all resulted in demerits. Hitchhiking, stealing, drinking, gambling, and possession of pornography could result in immediate dismissal. Every day, the cadets had to line up and face rigorous inspection. An officer wiped a white glove along the top of the lockers to check for dirt. A misspelling or missed punctuation on a term paper was enough to lower a grade.
The academy offered few distractions. Entertainment was limited to theater staged by an all-male cast and old movies in the chapel on Friday and Saturday nights. If a film included starlets, the cadets would erupt in howls and whistles, prompting commanders to order a punishing round of drill marches on the quadrangle. Only high-ranking student officers were allowed off campus in groups on Sunday afternoons, although cadets could leave for a meal with their parents. Fred Trump often came up to see his son. Once, when Fred arrived in a limousine driven by his chauffeur, Donald was too embarrassed to meet him. From then on, Fred drove his own Cadillac to check up on Donald.
The academy celebrated masculine excellence with a message carved above the school’s main entrance: COURAGEOUS AND GALLANT MEN HAVE PASSED THROUGH THESE PORTALS. When they weren’t studying or playing a sport, cadets were required to learn to clean an M1 rifle and fire a mortar. Physical brutality and verbal abuse were tolerated, even encouraged. Hazing was a part of freshman life, with upperclassmen pummeling new cadets with broom handles or forcing them to stand fully dressed in their uniforms atop radiators or in steam-filled showers until they passed out. Michael Scadron, a close Trump friend at the academy, said his own hazing culminated with upperclassmen requiring him to kiss the school’s mascot—a donkey—“on the ass.”
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