Donald Trump Has Always Been Obsessed With Status—Even If He Had to Borrow It

A couple of months after his thirteenth birthday, Donald Trump rode in his father’s Cadillac sixty miles north to rural Orange County, New York, just outside tiny Cornwall-on-Hudson. The car pulled into a narrow drive that led to the quadrangle of the New York Military Academy, a spread of grass about eighty yards long framed by three low-slung buildings: one for classes, one for sleeping, one for eating. That quad would be the center of his universe for the rest of his childhood. He would rarely again enjoy the comforts of the big house in Queens that his father had built for the family and staffed with help. He would no longer be called a student; he was now a cadet. He was issued an M1 rifle with the firing pin removed, a set of military like uniforms, and a single bed in Wright Hall, the smaller barracks for seventh- and eighth-grade boys.

Donald would be allowed to leave those grounds overnight only for major holidays and summers. His parents, Fred and Mary, made frequent trips north on weekends to take him off campus for a meal. During one visit, Mary cornered the mother of another student in his grade, George Michael Witek, who had easily transitioned to the academy from a strict Catholic school in Massachusetts. Donald’s mother seemed distraught and begged Mrs. Witek for a magic solution to make her insolent son listen, Witek later told Foreign Policy magazine.

As a resident of Wright Hall, Donald fell under the command of Theodore Dobias, a stout man and avid boxer who had graduated from the academy, served with the U.S. Army in World War II, and then returned to Cornwall for the rest of his working life. Given the honorary rank of major, Dobias was known among the students as “the Maj.” He lived in a house on campus with his wife and children and kept plaques on his office walls with motivational phrases like “Blame attitude for failure.” From Dobias’s perspective, young Donald, accustomed to a house with full-time help, did not know how to take care of himself, Dobias, who died in 2016, later told NPR. Donald was taught how to shine his shoes and make his bed to military boot-camp standards. When he failed to meet those standards, or stepped out of line, Dobias smacked him.

His days were ruled by rigid adherence to the clock. Loudspeakers blasted reveille at 6:00 a.m. The young boys of Wright Hall made their way to a communal bathroom in the basement, a tiled area with shower heads, toilets, and urinals, and no privacy partitions. After dressing in their uniforms, they would hustle outside to the quadrangle by 6:30 a.m., assembling in columns and grouped by platoon. The flag would be raised. They would march to the mess hall, and after eating, they would march back to their barracks to face a possible inspection. Then they would march to classes, mostly in the academic building, with its toy castle-like turrets rising at its corners and flanking its entrance. After classes, they would clean their neutered M1 rifles. On the open acres north of the quad, they would practice handling the weapon while marching, and then march some more. At about 3:00 p.m., everyone played sports, followed by showers and dinner in their uniforms. After eating, they marched back to the barracks for an enforced study period. The bugle would blow taps at 9:30 p.m. A census would be taken of cadets in their darkened rooms. Day was done.

Campus life had gone like that since the school was founded by a Civil War veteran in 1889. For generations, many boys, like Donald, had been sent to the academy because their parents felt they could not control them, or to pry them away from temptation. But the academy was not a reform school. Boys also arrived because their parents had divorced or died, or because they were planning for military careers. A dozen or so boys from wealthy Latin American families arrived each fall. The draw was the promise that these boys would learn self-discipline.

If military veterans like Dobias set the emotional tone at the academy, the frontline management of younger cadets fell to the older students through a hierarchical military ranking structure. Power flowed downward from the first captain and his staff, beginning with the eight cadet captains who were each in charge of a company of thirty to forty boys. Lieutenants, sergeants, and corporals carried out the wishes of the captains, and everyone else in the company was at the rank of private. Rank came with privilege and power. The leadership teams were given broad authority to enforce standards—maintaining rooms, uniforms, weapons, displaying proper marching technique, snapping crisply to attention when older cadets walked past—through inspections and punishments, several former cadets told us. The older students enforced what one cadet called “New Guy Rules,” which essentially meant younger students were treated as lesser humans. When an older student passed in the hall, all the New Guys slammed their backs against a wall and shouted, “Sorry to be in your way, sir!” Failing to hit the wall hard enough could result in punishment, former cadet Peter Ticktin wrote in a little-noticed memoir.

To solidify control, the older children often relied on violence, or the perceived threat of violence. Whacks with a broomstick to a bare backside were a common tool. Kicks to the groin were not unusual.

Douglas Reichel, a classmate one year behind Donald, was thirteen the day he was issued an M1. It was a thing of wonder for him, even without a firing pin or ammunition. He had never held a firearm before, and he marveled at its long black barrel and heavy wooden stock. Outside in the quad, he raised the rifle above his shoulder and aimed at a tree. Just then, the captain of his company kicked him hard in the groin. He spent more than a week in the infirmary. In his mind, that first day set the tone for his five years at the academy. He would run away from school twice, only to be discovered and beaten upon his return. “There wasn’t a day when I didn’t want to be out of that school,” Reichel told us. He saw Donald and a few other cadets as favored nations, floating above the constant threat of taunting and beatings. In his mind, Donald lived “the life of a privileged kid.”

The military training, such as it was, focused overwhelmingly on executing a precise definition of neatness. There were infrequent days when the firing pins were placed back in the M1s for target practice, or the cadets learned the proper use of a mortar launcher. Standing at perfect attention and marching in synchronicity occupied a tremendous amount of time. But no skills were more frequently drilled into cadets than polishing shoes and belt buckles, making beds to an exacting pattern, and folding laundry with crisp 90-degree angles, all while older children cast judgment and distributed abuse for minute failures or demonstrations of insubordination.

Donald excelled at the domestic hygiene requirements and demanded perfection in those skills from other cadets. He once lost his temper at the sight of a fellow cadet’s halfheartedly made bed and ripped the sheets off in a fit of rage. The cadet, Theodore Levine, who was four foot eleven, later told NPR that he grew angry and threw a boot at Donald, then took a swing at him with a stick. Donald charged at the smaller cadet and seemed to be trying to push him out a window when two other cadets intervened. The fight with Levine was the only time many of Donald’s classmates could recall him getting into a physical altercation.

All cadets were pushed to play on the school’s sports teams. Donald played one year each of varsity football and soccer, and three years of varsity baseball, still his favorite sport. Dobias coached Donald during his time on the junior varsity team, and during his senior year Donald was named a co-captain.

The academy, a small school with roughly ninety students in each grade, was not a standout in regional athletics. The baseball team played against other small private and parochial schools and won just five of its twelve games in Donald’s senior year. We found box scores for five of those games in old newspapers. The results show Donald hit safely only once in eighteen at bats, a stunningly poor batting average of 0.055. Donald would later claim to have been the best high school baseball player in the state.

Because the academy’s soccer team had at least ten players from Latin America during an era when the sport was not widely popular in the United States, many on campus perceived the soccer team to be the school’s strongest. But that season did not go well either during Donald’s varsity season: the soccer team won three of its eleven games.

Regardless of wins and losses or his personal performance, playing on two varsity teams in a school that stressed athletics as a component of development granted Donald some standing in the barracks.

Donald returned each summer to the family home, which sat above a curving and tree-lined street among the homes of doctors, lawyers and business owners. He would spend much of those months accompanying his father to work and following orders: Hose down a rubble pile on a construction site. Survey repairs of empty units. Paint a hallway. He was the small fish that everyone knew would soon be the big fish.

“He’s got to learn while he’s not in school,” Fred told anyone who asked about the blond-haired scion holding a shovel, the New York Daily News once reported.

During his junior year at the academy, Donald held the rank of supply sergeant in his company. He was put in charge of a storage room full of M1 rifles and made sure they were oiled and in good working order. Sandy McIntosh, who attended the military academy with Donald, told us he saw the supply sergeant job as perfect for him because “he didn’t have to deal with people.”

Supply sergeant was not a rank that necessarily suggested a trajectory to the top of the heap. But then, in September of his final year, a surprise came from the administration: Donald would be promoted to captain of Company A, putting him in one of the top leadership positions on campus.

McIntosh was one of twenty-nine “privates” who fell under his authority. They noticed that after dinner, Donald would adjourn to his barracks room and lock the door. He left discipline and evening bed checks to his underlings and paid no attention to what was going on outside during study hours, a favorite time for older cadets looking to harass their younger peers.

That detached leadership style came at a cost. During his first month as a company captain, one of Donald’s sergeants shoved a freshman cadet named Lee Raoul Ains hard against a wall, an incident recounted to us by several former cadets and first reported by The Washington Post. Ains complained, and the school demoted the offending sergeant. The administration also reassigned Donald. Dobias, long Trump’s most stalwart defender from the academy, later acknowledged that Donald had been transferred because he had not monitored his charges closely enough. He was allowed to keep the title of captain but now served as a training officer without a company directly under his command.

In his new role, Donald joined the central staff of Witek, the top-ranked student, whose mother Mary Trump had once asked for advice. Witek, who later changed his last name to White, was told by the administration that another captain on his staff, William Specht, would take over Company A in order to get Trump “out of the barracks.” Specht, who as a junior had been promoted to the second-highest rank of lieutenant, was disappointed but quickly got Company A under control. Still, Donald insisted that joining Witek’s staff had been a promotion.

It was the first of several episodes that led Witek to believe Fred Trump held sway over the academy’s administrators. “His father was rich, and he was protected,” Witek later told Foreign Policy. “They directly ordered me to stay away from Trump. Everybody knew Fred was pulling out his checkbook.”

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Soon after, the cadets were preparing to march in the annual Columbus Day Parade in Manhattan, as they had done in recent years. Witek was surprised when Anthony “Ace” Castellano, the assistant commandant of cadets, directed him to put Donald at the front of the parade. Witek assumed that Fred Trump had complained to the school about his son being pushed out of the prominent company leadership role, according to emails written by Witek that we obtained.

Whatever the reason, on October 12, 1963, Donald led the specially assembled company of cadets down Fifth Avenue, past some of the premiere addresses in the city of his birth. Some of the cadets marching behind him wondered how it could be that Trump was in front and Witek, the highest-ranking cadet in the school and the senior class president, marched behind him. Trump arrived first at St. Patrick’s Cathedral, where he met Cardinal Francis Spellman. Donald would always claim marching in the front of the parade was evidence of his “elite” status at the academy.

Back on campus, Witek assembled his staff for a yearbook photo. They met on the wide-open field behind the buildings surrounding the quad. They wore their finest dress uniforms: tar bucket parade hats with tall feather plumes and chin straps across their lower lips, waist-cut dark jackets with three columns of brass buttons, and white shoulder belts across their chests. As they marched side by side across an empty field, Witek commanded his staff to draw and present their sabres. All except Trump followed the precise movement they had rehearsed for four years that ended with the blades coming to rest on the inside of their shoulders, Witek told Foreign Policy. Facing forward, Witek heard one of his captains tell Donald again to draw his sword. Again, he did not. The photographer snapped the photo. Donald was the only member of the senior staff shown in the yearbook photo with his sword still sheathed. Witek later heard that Trump pointed out the photograph to fellow cadets as a boast of his defiance.

If Donald resented taking orders from a contemporary like Witek, he still craved the tokens of status conferred by the system. Like most cadets, he had earned a few medals for good conduct and being neat and orderly. But his friend, Michael Scadron, had a full dozen by their senior year. On the day yearbook portraits were being taken, Donald showed up in Scadron’s barracks room and asked to borrow his dress jacket with the medals attached, Scandron told us. Donald wore those medals for the portrait, perplexing some of his fellow cadets. “He’s wearing my medals on his uniform,” Scadron later recalled. “I didn’t care one way or the other.”

From Trump’s perspective, Scadron came from another world. Scadron’s father, Harold, had managed boxers in the 1930s and 1940s, most famously the fighter Bob Olin, who in 1934 won a light heavyweight championship in a fifteen-round match at Madison Square Garden. Scadron’s mother, fifteen years younger than Harold, left her family when Michael was young to pursue drinking and cavorting full-time in Los Angeles. Young Michael bounced between coasts for a few years before begging his father to send him to the military academy for some sense of stability.

Scadron, who learned to box from his father, found a home in the culture that valued such things. He could play by the rules at the academy, but he had a temper. One day in the spring of 1964, in Scadron’s telling, he was holding a meeting with his squad when a younger cadet from a wealthy family called him “a dirty Jew bastard.” Scadron, whose father was raised in the Jewish faith, lost it. “I decked him, and after I decked him, I kept on decking him.” In his room, Scadron kept a two-foot-long wooden stick with a metal chain attached to one end. He had mostly used it as a theatrical prop, swinging it around like a movie villain in a dusty chariot race with Ben-Hur. But in a fit of rage that day, he used the crude device as a weapon: “I may have hit him with it, because when he called my father a dirty Jew bastard, all bets were off.”

The culture of hazing at the school had become a liability. Scadron was expelled, and the superintendent of the academy and two other top administrators were forced to resign. The police were notified, but Scadron was not formally charged. He graduated from another high school and moved to Ohio to attend Kenyon College, where he had been accepted prior to the incident. His individual portrait was purged from the military academy yearbook, even though his medals made a cameo appearance on Donald Trump’s chest. Scadron would lose track of nearly everyone else from those years except Donald Trump, who would hire him a decade later.

It was the first of many such relationships in Trump’s life. He would be drawn to men who displayed a penchant for violence, and wax sentimentally about the days when, in his perception, society accepted resolving disputes with physical violence.

On a warm day in June 1964, hundreds of cadets and their families gathered in front of a stage on the quadrangle for the annual graduation commencement ceremony. Fred and Mary made the drive north. If they had been briefed by their son, they might have arrived expecting to see him endlessly feted. The list of awards to be handed out to the top performers spanned five pages of the program. There were the top ten cadets—more than 10 percent of the entire class—graduating “with distinction.” There was the Head Boy Gold Medal, awarded for earning the highest marks in conduct, military, and scholastic work. There were more than a dozen medals for accomplishment in individual subjects. The name Trump would not be mentioned.

For the top honor, the Achievement Alumni Award, seven cadets were nominated by classmates, the headmaster, and the commandant. Donald Trump was not among them. The winner was George Witek. His name would be added to the list of prior winners on a large memorial near the flag in the quad, something approaching military academy immortality.

Donald received one distinction. Like all fourteen captains, he was given an honorary saber.

Witek was called to the stage to accept honors so many times that he barely had time to warm his chair. No cadet took success at the academy more seriously. Yet Witek’s assessment of the school’s military training would quickly diminish after he enlisted in the army.

“When I got into basic training,” Witek later said, “I realized very quickly that at the New York Military Academy we were just play-acting. What we had been taught was a sort of surface military thing.”

With U.S. involvement in Vietnam escalating, many of Donald’s classmates enlisted or were drafted. But he would never put his military education to the test. He obtained his first draft deferment shortly after graduating high school, and later received a medical exemption when a doctor who rented office space from Fred Trump gave him a diagnosis of bone spurs in his heels. The deferments would mark the start of Trump’s long and complicated relationship with those who served. Trump, who refused our requests for an interview, later told biographer Michael D’Antonio that he saw his time in high school as superior to actual military service: “I always felt that I was in the military because I, in a way, had more training militarily than a lot of the guys that go into the military.”

Excerpted from: LUCKY LOSER: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success by Russ Buettner and Susanne Craig. Reprinted by arrangement with Penguin Press, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2024, Russ Buettner and Susanne Craig.