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Donald John Trump (D.T.) from the 1964 yearbook of the New York Military Academy.PHOTO ILLUSTRATION: THE GLOBE AND MAIL

Frank Chamandy is an investment adviser and portfolio manager in Montreal.

New York Military Academy is a college preparatory school almost 100 kilometres’ north of New York. Modelled after West Point, it’s one of the oldest military schools in the United States, having been founded in 1889 by a Civil War veteran.

Its student population was made up of boys from the U.S. and all around the world. There were rich kids and kids from families who struggled to pay the tuition fees. There were kids who should have been in reform school, but were sent to military school instead. There were kids whose families had ties to organized crime, and one whose grandfather was an assassinated dictator.

NYMA enjoyed its heyday in the 1960s, when it reached its peak enrolment of 525 students – students that, at different points in that decade, included me and U.S. President Donald Trump.

A handout from the 1964 yearbook of the New York Military Academy shows Donald Trump when he was a junior high school student there.HANDOUT/The New York Times News Service

That was an eventful time in the history of the United States. Lyndon B. Johnson was president. The Vietnam War was raging. Race riots were roiling cities throughout the country. Martin Luther King Jr. and Robert Kennedy fell to assassins' bullets. My best friend at NYMA, one of a handful of Black students, died at the hands of muggers in New York less than a decade after graduation. Despite all this, the United States of America was the greatest country in the world – and still isn’t.

Mr. Trump is five years older than me. When I entered NYMA at the age of 12 in 1964, he had just graduated; I never met him. But the paths that we followed at the school were surprisingly similar. We were both Supply Sergeants in our junior year and cadet captains in our senior year – the equivalent of prefects, at other private schools.

And most importantly, we shared a military instructor, tactical officer and role model: Major Theodore Dobias.

Major Dobias, who was born in Czechoslovakia, attended NYMA starting in 1942. As soon as he turned 17, he left school to join the U.S. army and fought in Italy. He was captured and escaped. He was a hardened veteran of the Second World War.

At the end of the war, Major Dobias returned to NYMA to finish his final two years of school. He was a star athlete and fierce competitor who lettered in many sports: boxing, lacrosse, baseball, basketball. He was captain of the football team, a cadet captain and the president of his senior class.

When he graduated, Major Dobias stayed on as a staff officer, with the honorary rank of major, and served NYMA in many capacities for 50 uninterrupted years, during which he ascended the ranks to colonel. He also coached varsity baseball, boxing and junior varsity football. He was rough and demanding and had the reputation of being the school’s toughest instructor – an imposing figure who cadets knew at the time simply as “The Maj.”

During the years that I was at NYMA, Major Dobias oversaw Wright Hall, a barracks that housed middle-school students aged 14 and 15. Cadets were supervised by other student officers, but The Maj was always around. He lived next door to the barracks. He was forever calling company meetings. We would stand in formation in the lobby of the barracks, and he would stand on the landing near the bottom of the stairs and lecture to us. There was always a theme. A lot of emphasis was placed on military and athletic excellence. Academic excellence was also encouraged, but not as much.

There were famous sayings posted on the bulletin board near his office. He would often pick a quote and turn it into a lecture. One of his favourites was “winning isn’t everything – it’s the only thing.” He pushed us to win. If you weren’t a winner, you were a loser, plain and simple. “When the going gets tough, the tough get going” – that was another of his favourites. You had to be tough! He was always present and pushing us. There was a communal shower in the basement of Wright Hall where cadets were required to shower every day, and although he had a house on campus with his wife and kids, he often showered with the students. He was always in your face.

When I was a 15-year-old sophomore, I made the varsity wrestling team as its smallest member. I was very successful and won most of my matches by pinning my opponents, but the wrestling workouts and the fasting to make my weight class were hard on my body, and damaging to my grades. But my teachers would beam about my performances; in biology class, my teacher would hand me press clippings of my victories from the local newspaper, and my English teacher – my wrestling coach – would call me “champ” in class. Only my French teacher saw my struggles and he suggested I should quit wrestling – but I didn’t listen to him.

Toward the end of the season, after coming back from vacation, I found myself out of shape and overweight. I had to lose six pounds in just a few days so I could make weight at 98 pounds. I was undefeated and cocky. I remember thinking to myself, as I was leaving the locker room prior to my match: “May the better man win.” I thought that was me, but I was wrong. I lost my match – my first defeat.

We returned to school late that evening, and I was feeling very down. The next morning, we stood outside in formation waiting to be marched into the mess hall for breakfast, and Major Dobias was there, inspecting the cadets. He came right up to me, looked me in the eye and said: “I heard you lost.” He shook his head in disgust and walked away.

That happened 53 years ago, and I remember it like it was yesterday.

I lost that match near the end of the season and just before the Westchester County Wrestling Championships, a yearly tournament with schools from around New York State. It was a big deal. That year, our school was hosting the tournament in our new state-of-the-art gymnasium. Although basketball was the No. 1 winter sport in the U.S., almost the whole school – 500 strong – turned out to watch the wrestling championships.

I was seeded second in the tournament, outranked only by a senior from another college preparatory school, McBurney; he was two grades higher than me and won the silver medal the year before. I won all my preliminary matches and made it to the finals, which were to be held Saturday night. The senior from McBurney was my opponent in the finals. I was a little intimidated.

That afternoon before the evening matches, Major Dobias called me into his office. He wanted to know what my strategy for the finals was going to be, and I told him that I was planning to be defensive. He practically tore my head off, swearing at me, calling me an “idiot.” “You can’t be defensive,” he shouted. “You have to kill this guy!”

He wouldn’t let up on me. He ranted on. He said that if I wasn’t the aggressor I would lose. He was angry. I remember pretending to agree with him, thinking I would stick with my original plan. He could see that I wasn’t convinced and he wouldn’t let me go. This man didn’t take “no” or “maybe” for an answer, and wouldn’t dismiss me until he was convinced that I would do what he said. He went on and on about how I had to be the aggressor. He hated quitters – quitters were losers. You never gave up. Eventually, I was finally dismissed and left his office.

That night, the whole school turned out to watch my match. I didn’t realize what effect Major Dobias’s speech had had on me until I got to the mat, but I was aggressive from the starting whistle – and as the match went on, my confidence grew. I didn’t back down and pinned my opponent in the second of three periods, winning the gold medal to a thundering ovation. I thought the gym rafters would come down! I was so excited. I must have jumped three feet off the ground. Major Dobias was the first one to greet me.

This is the effect he had on people. He was a bully. He was tough and unrelenting. Maybe he even brainwashed us. But he got results.

For most of us, Major Dobias was a temporary figure in our lives. But for Mr. Trump, he was more – much more. The man he affectionately called “Dobie” was a mentor and an important presence in his life, not to mention his baseball coach; Major Dobias told NPR that he admired the way Mr. Trump “wanted to be best. Not better.” Indeed, months before the 2016 presidential election, The Maj was at his former cadet’s side one last time, speaking at a campaign event at NYMA and declaring to the crowd, “He’ll make a damn good President, won’t he?”

Major Dobias didn’t make it to election day – he died in June, 2016, at the age of 90. But in an odd way, The Maj – a mentor, a role model, a bully, a master psychological manipulator, a surrogate father – lives on. I have thought more about Major Dobias in the past few years than in the previous 50; after all, it’s hard not to think about him whenever I hear the President speak.

Major Theodore Dobias may have changed the course of history. He certainly left an indelible mark on Mr. Trump – and in many ways, on me.

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