• • •
DONALD’S COMPETITIVE DRIVE TOOK over as he learned to master the academy. He won medals for neatness and order. He loved competing to win contests for cleanest room, shiniest shoes, and best-made bed. For the first time, he took pride in his grades; he grew angry when a study partner scored higher on a chemistry test, even questioning whether he had cheated. Donald also learned to manage Dobias, projecting strength—especially in sports—without appearing to undermine the sergeant. “I figured out what it would take to get Dobias on my side,” Trump said. “I finessed him. It helped that I was a good athlete, since he was the baseball coach and I was the captain of the team. But I also learned how to play him.”
To fellow cadets, Donald could be friendly, aloof, and cocky, once telling Jeff Orteneau, “I’m going to be famous one day.” When meeting classmates for the first time, he liked to ask, “What does your father do?” Most of Donald’s friends knew that his family was wealthy because he would talk about his father’s business. Donald told David Smith, his senior-year roommate, that Fred Trump’s wealth doubled every time he completed a project. “He was self-confident and very soft-spoken, believe it or not, as if he knew he was just passing time until he went on to something greater,” said classmate Michael Pitkow. Despite his affluence, Donald’s tastes were often plebeian. In the waning months of the Eisenhower administration, in a culture defined by conformity, Donald used the record player in his dorm room mostly to listen to Elvis Presley and Johnny Mathis albums. Sometimes, Donald would screw an ultraviolet lightbulb into the overhead socket and announce to his roommate that it was time to tan. “We’re going to the beach,” he’d say.
As a senior, Donald drew notice for bringing women to campus and showing them around. “They were beautiful, gorgeous women, dressed out of Saks Fifth Avenue,” said classmate George White. Trump was never shy about judging a girl’s appearance, pronouncing one of White’s visitors a “dog.” Ernie Kirk went on double dates with Donald and two girls who lived in town. Because the boys weren’t allowed off grounds, the girls came to campus, where they watched a ball game and had burgers and Cokes in the canteen. Donald was cordial and talkative with his date, a brunette. A few months later, Trump was identified as “Ladies’ Man” in his senior yearbook, posing for a photo alongside an academy secretary.
On occasion, Donald demonstrated that he was still capable of the aggression that had defined him at Kew-Forest, and he seemed to enjoy wielding authority. As a junior supply sergeant in Company E, Trump commanded that a cadet be struck on the backside with a broomstick for breaking formation. On another day, when he was on inspection duty, Trump came upon fellow student Ted Levine’s unmade bed. Trump ripped the sheets off and threw them on the floor. Levine, a foot shorter than Trump, threw a combat boot at Donald, then hit him with a broomstick. Infuriated, Trump grabbed Levine and tried to push him out a second-floor window, Levine recalled. Two other cadets intervened to prevent Levine from falling. Trump and Levine clashed again when they became roommates. Disgusted by Levine’s messiness, Trump often shouted at him to clean up. Trump, his roommate would later say, would try to “break” anyone who did not bend to his will.
• • •
AS AT KEW-FOREST, TRUMP could rely on his athletic ability to win respect from his teachers and classmates. In his second year at NYMA, Trump played on the freshman football and baseball teams, the latter coached by Dobias. By his sophomore year, as he shed baby fat and continued to grow, Trump had made the varsity in both sports. He particularly excelled at baseball, playing first base and developing a reputation for stretching his long body to scoop up balls that the team’s shortstop, Gerald Paige, threw in the dirt. Donald could also swing the bat, inspiring a caption beneath an action photo in the yearbook that read, “Trump swings . . . then HITS.” A headline in the local paper—“Trump Wins Game for NYMA”—may have been the first to celebrate his exploits. “It felt good seeing my name in print,” Trump said years later. “How many people are in print? Nobody’s in print. It was the first time I was ever in the newspaper. I thought it was amazing.” Dobias taught his players the line famously attributed to legendary Green Bay Packers head coach Vince Lombardi: “I taught them that winning wasn’t everything, it was the only thing,” Dobias said. “Donald picked right up on this. He would tell his teammates, ‘We’re out here for a purpose. To win.’ He always had to be number one, in everything. He was a conniver even then. A real pain in the ass. He would do anything to win . . . [Trump] just wanted to be first, in everything, and he wanted people to know he was first.”
On the football team, Trump played tight end for two years. He wasn’t the fastest player, but he was a “big, strong kid” who was “hard to bring down,” said Paige, a running back. As a junior, however, Trump quit the team. He didn’t like the head coach, and the feeling was apparently mutual. “The coach was nasty to him,” Levine said. Trump “got personally abused by authority and was not appreciated.” Trump’s teammates, who valued his play on the field, were angry that he left the team. John Cino, the head coach, had his own theory: Trump quit, he said, because his father wanted him to concentrate on academics.
Off the field, Trump rose steadily from private to corporal to, in his junior year, supply sergeant, an important if dull position that required him to procure supplies for his company, including deactivated M1 rifles. New cadets were required to meticulously clean their weapons. Trump went further, demanding that the boys memorize their rifle numbers. “Being a new guy, it was overwhelming,” said Jack Serafin, who was a freshman when Trump was a supply sergeant. “But you could always go to Donald and he would figure out how to get things done.”
• • •
IN JUNE OF 1963, as Donald was completing his junior year, the National Guard escorted two black students into the University of Alabama, pushing their way past Governor George Wallace as he made his stand in the schoolhouse door. Three months later, New York Military Academy accepted its first two African American cadets. On his first day at the academy, after arriving from Harlem, Vincent Cunningham was tying his shoes when a corporal called him a “nigger.” Cunningham knocked the corporal down and wound up in a commandant’s office. The abuse continued all year. “You had to have thick skin and know how to carry yourself,” Cunningham said. “If you overreacted to everything and were in disagreement to everything, they’d make your life miserable.” David Prince Thomas, another black student, got into a fight on his first day after a white student called him a “jungle bunny.” At night, fellow cadets would call up toward Thomas’s room, saying the Ku Klux Klan was coming to get him. “It was almost socially accepted,” Peter Ticktin, a classmate of Donald’s, said of the abuse. But when Ticktin and Trump heard a student call a black cadet “nigger,” they were both disgusted, Ticktin recalled.
On November 22, 1963, a Friday, Donald was sitting in class when an alarm bell rang. The cadets were called to the chapel, where an administrator announced that President Kennedy had been assassinated. At home, Donald had grown up absorbing his father’s enthusiasm for Republicans such as Barry Goldwater. Donald had gone to school wearing an I LIKE IKE button for Eisenhower. Yet because of his business interests, his father also had many allies in New York’s Democratic establishment. Kennedy’s death was a seismic moment, and many of the cadets assembled that afternoon broke out into tears at the news. It was an unsettling time: along with racial and political crises, US involvement in Vietnam was escalating.
At NYMA, Trump was focused on more personal tumult as senior year unfolded. Scadron, his friend, left the academy after a younger cadet accused him of beating him with a stick. At the same time, Trump was promoted to captain of A Company, a prestigious position. Ticktin served as Trump’s platoon sergeant, helping him “set the pace for all the parades” and managing their forty-five-man platoon. As a captain, Trump was “even-keeled,” Ticktin said, inspiring respect without screaming at his cadets. Often, he left his officers to manage the younge
r cadets. “You just didn’t want to disappoint him,” Ticktin said. “I came back from a trip to New York once, and I was five minutes late, and he just looked at me. He never yelled at anyone. He would just look at you, the eyebrows kind of raised. The kind of look that said you can’t disappoint him.”
A month into the school year, one of Trump’s sergeants shoved a new cadet named Lee Ains against the wall after the freshman didn’t stand to attention fast enough. Ains complained. With administrators still reeling from other hazing incidents, a colonel relieved Trump of duty in the barracks and reassigned him to the academic building as a battalion training officer. “They felt he wasn’t paying attention to his other officers as closely as he should have,” said Ains, who left the school at the end of the year. By Trump’s account, his transfer was a promotion and had nothing to do with hazing under his command. “I did a good job, and that’s why I got elevated,” he said. “You don’t get elevated if you partake in hazing.” After his transfer, Trump was put in charge of a special drill team for New York City’s Columbus Day parade. In white gloves and dressed in full uniform, Trump led the procession south along Fifth Avenue toward St. Patrick’s Cathedral, where he shook hands with Francis Cardinal Spellman. Turning to Major Anthony “Ace” Castellano, one of NYMA’s commanders, Trump said, “You know what, Ace? I’d really like to own some of this real estate someday.”
When Trump graduated from NYMA in May of 1964, striding across the quadrangle in full uniform in front of his family, his ambition was to follow his father into real estate. Despite his military preparation, Trump apparently had little desire to go to war. He registered for the draft—he was listed at six feet two, 180 pounds, with birthmarks on both heels—but his decision to go straight to college earned him the first of four educational draft deferments on July 28, 1964. For a time, he flirted with signing up for film school at the University of Southern California—reflecting his lifelong love of movies—but he enrolled instead at Fordham University because he wanted to be closer to home.
In the summer between high school and college, Donald worked for Fred, traveling to Cincinnati, where his father had purchased a run-down, twelve-hundred-unit apartment complex called Swifton Village for $5.7 million. Fred would leave his son in Cincinnati for a week at a time to take care of menial tasks. “He’d get in there and work with us,” remembered Roy Knight, a Swifton Village maintenance man. “He wasn’t skilled, but he’d do yard work and clean up—whatever needed to be done.”
• • •
STARTING IN FALL OF 1964, Trump commuted from Jamaica Estates to Fordham’s leafy Bronx campus in his red Austin-Healey. After being away at school for five years, Donald could spend more time with his father, joining him that November for the opening ceremony for the elegant, daring Verrazano-Narrows Bridge, then the world’s longest suspension bridge, connecting Brooklyn and Staten Island. Amid the pageantry, Donald noticed that city officials barely acknowledged the bridge’s eighty-five-year-old designer, Othmar Ammann. Although the day had been sunny and cloudless, Trump would remember pouring rain years later when he recalled Ammann’s standing off to the side, alone. “Nobody even mentioned his name,” Trump said. “I realized then and there that if you let people treat you how they want, you’ll be made a fool. I realized then and there something I would never forget: I don’t want to be made anybody’s sucker.”
At Fordham, Trump’s wealth was evident to classmates, most of them public school graduates from working- and middle-class families across the New York area. At a time when college students were beginning to experiment with drugs and dressing more casually, Trump showed up for school in a three-piece suit and carrying a briefcase. In classes, Trump often raised his hand to participate. Yet what caught the attention of Robert Klein, an accounting major who sat next to him in philosophy class, were Donald’s doodles. He drew pictures of buildings—skyscrapers. Klein discovered that Trump was not like his classmates in other ways, too. One afternoon, Donald invited Klein to a Mets game. Donald drove his convertible with his friend to Shea Stadium, where an attendant parked the car for Donald. He and Klein sat in the stadium’s front row, near the team’s owner, Joan Payson.
Trump joined Fordham’s squash team, cramming with teammates into his coach’s station wagon for rides to practice. Squash was not Donald’s game, but he was an eager learner and was aggressive on the court, preferring to smash the ball past opponents than to outlast them in a volley. “Way to go, Trumpie!” his teammates shouted after Donald won a decisive match. “He had a certain aura,” said Rich Marrin, a teammate. “He didn’t have tantrums, and he was never late. If anything, he was more of a gentleman than we were, more refined, as if brought up in a stricter family, with more emphasis on manners. We weren’t that rowdy, but we didn’t always know the right forks.” Trump made the first-string team, which traveled across the Northeast and mid-Atlantic. He sometimes drove teammates in his sports car, requiring them to chip in for gas and tolls even though the coach gave Trump travel money. Sometimes, at practice, a teammate would look over to see Trump, taking a break, reading the Wall Street Journal or the New York Times. On road trips to Yale and Georgetown, he snuck out at night with teammates to bars, even though he did not drink. After a crushing loss to the Naval Academy in Annapolis, Trump tried to boost his team’s spirits. As they were driving back to New York, he told a teammate to pull over at a Montgomery Ward department store, where Donald bought golf clubs, tees, and dozens of balls, which they took to a bluff overlooking Chesapeake Bay. Trump grabbed a club and hit a few balls into the water, inspiring his teammates to join in. After all the balls were gone, Trump and his teammates got back into the car, leaving the golf clubs on the side of the road.
Yet, for all the fun he seemed to have with his team, Trump also exuded restlessness at Fordham, as if the school’s reputation and its culture did not meet his standards. Brian Fitzgibbon, who lived near Donald in Queens, sometimes commuted to school with him in Donald’s car and did not think Trump “had a keen sense of belonging at Fordham. His family wealth and the fact that he was not Catholic may have made him feel different from others.” Trump, he said, sometimes complained “that there were too many Italian and Irish students at Fordham,” an assertion that struck Fitzgibbon as “elitist.” Fitzgibbon suspected that Trump’s attitude reflected his belief that he had really always belonged at an Ivy League school. After his sophomore year, Trump got his wish, transferring to the University of Pennsylvania. He left Fordham behind without saying good-bye to his buddies on the squash team.
• • •
TRUMP ARRIVED AT THE University of Pennsylvania’s Wharton School in the fall of 1966 as a man in a hurry. In the school’s tiny real estate department, Trump’s bragging stood out from the start. The kid with the big blond mop of hair told classmates that he was going to be the next Bill Zeckendorf, the Manhattan developer who once owned the Chrysler Building and amassed land for the United Nations headquarters (and who was also the son of a major builder). Trump promised he’d be even bigger and better than Zeckendorf.
Trump’s two years at the sole Ivy League school with an undergraduate business school would be the only time he ever lived outside New York, but even then, he returned home frequently on weekends to work with his father. Trump saw Wharton from the beginning as a place to pick up a patina of prestige. “Perhaps the most important thing I learned at Wharton was not to be overly impressed by academic credentials,” Trump said. “It didn’t take me long to realize that there was nothing particularly awesome or exceptional about my classmates, and that I could compete just fine. The other important thing I got from Wharton was a Wharton degree. In my opinion, that degree doesn’t prove much, but a lot of people I do business with take it very seriously.”
Yet Trump himself would come to take Wharton very seriously. Wharton became a name to be dropped, another “best” to burnish the Trump brand. For a time, Trump bragged of being a top student among his 333 Wharton classmates, even claimin
g to have been first in the class. But Trump is not included on the honor roll printed in the Daily Pennsylvanian, the student newspaper, and classmates don’t recall Trump as an exceptional student. “Trump was not what you would call an ‘intellectual,’ ” said Louis Calomaris, his classmate. “He wasn’t a dumb guy. He had a specific interest. I don’t think he ever studied for an exam. Trump was interested in trading and leveraged deals. . . . He did what it took to get through the program.” Trump lived off campus in a modest apartment and left town most weekends. He wasn’t prominent in extracurricular activities. Many classmates don’t remember him at all.
At the height of the anti–Vietnam War protests on college campuses, in the first, volatile years of the Nixon administration, Penn students staged sit-ins, demonstrating against university contracts with the US military to research biological weapons and potent herbicides. Trump, like many other Wharton students, steered clear of the campus unrest; his focus was on getting his career going. Soon after he arrived at Penn, Trump had his second US military physical, but he remained exempt from the draft because he was still a student. Trump would be declared 1-A—eligible for service—after he completed college, in 1968. But another armed forces physical that fall ended with his being classified 1-Y, medically disqualified except in case of national emergency. Military records do not detail the reason for that finding; Trump said it was because he had bone spurs in both heels. In 1969, young men who shared Trump’s birthday—June 14—drew number 356 out of 366 in the draft lottery, almost certainly sparing them from mandatory military service. But Trump didn’t need the luck of the lottery because his medical disqualification remained in effect through 1972, when it was changed to 4-F, meaning not qualified for service. (During his presidential campaign, a Trump spokesman said that Trump was “not a fan of the Vietnam War, yet another disaster for our country, [but] had his draft number been selected, he would have gladly served.”)
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