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.”