“No, those remarks absolutely didn’t surprise me. In my dealings with him he was a heartless, obnoxious son of a bitch,” White told me in an interview over the weekend. 

According to White and other former classmates at the academy, Trump’s five years there, coupled with the disregard for U.S. military traditions he learned at his father’s knee, helps explain a great deal of the president’s reported contempt for those who fought, died, or were wounded in America’s wars, as well as his skeptical view of the need for the United States to fight in places like Vietnam and Iraq.

According to the Atlantic magazine, during a trip to France to mark the 100th anniversary of the end of World War I, Trump referred to the more than 1,800 U.S. Marines who lost their lives at Belleau Wood as “suckers.” Indicating that he didn’t understand why the United States had intervened at all in Europe in 1917, Trump also reportedly asked aides, “Who were the good guys in this war?” 

The Atlantic article, portions of which have been corroborated by the Associated Press, the Washington Post, and Fox News, also reported that when Trump aborted a visit to another World War I cemetery, blaming the weather, he remarked, “Why should I go to that cemetery? It’s filled with losers.” In addition, Trump reportedly said that the presence of maimed U.S. veterans would upset spectators at a military parade, commenting, “Nobody wants to see that.”

Trump’s comments appeared to be in line with the attitude he reportedly evinced on Memorial Day 2017, when he visited the grave of 1st Lt. Robert Kelly, the son of his then-homeland security secretary and later chief of staff John Kelly. Standing at the grave of the younger Kelly, who died in Afghanistan in 2010, Trump reportedly turned to the secretary and said: “I don’t get it. What was in it for them?”

Trump and the White House have denied reports about his disdain for the sacrifices of the U.S. military. “If people really exist that would have said that, they’re lowlifes and they’re liars,” Trump told reporters on Sept. 3. “And I would be willing to swear on anything that I never said that about our fallen heroes. There is nobody that respects them more.”

In the aftermath of the controversy over his demeaning of U.S. service members, Trump has sought to portray himself as an anti-war candidate who has faced down trigger-happy military service chiefs and will pull out of “endless wars” to keep soldiers safe. 

“I’m not saying the military is in love with me—the soldiers are,” Trump said at a news conference Monday. “The top people in the Pentagon probably aren’t, because they want to do nothing but fight wars so that all of those wonderful companies that make the bombs and make the planes and make everything else stay happy. But we’re getting out of the endless wars, you know how we’re doing.”

Trump is certainly not alone in questioning the wisdom of U.S. military involvement in Vietnam and Iraq, which are now widely considered major strategic errors, or even in World War I—a still-debated intervention orchestrated by a formerly pacifist president, Woodrow Wilson. White, Trump’s former superior at the New York Military Academy, said he agrees with the basic idea of the president’s opposition to many overseas deployments, saying that if it weren’t for Trump’s contemptuous attitude toward the military, “he’d be perfect.”

Since taking office, many of Trump’s actions have borne out that oft-repeated skepticism about U.S. military deployments abroad. In 2018, he announced an abrupt withdrawal of troops from Afghanistan, even before formally launching peace talks with the Taliban, and said he wanted to leave Syria as well. In 2019 he was widely criticized for abruptly abandoning Kurdish fighters in Syria who had fought and died to help the United States remove the Islamic State. This July, Trump also announced the withdrawal of nearly 12,000 U.S. troops from Germany, with no strategic rationale given. 

Against that, Trump has lavished money on the Pentagon since taking office, boosting defense spending in each of the last three years, while he has yet to wind down the “endless war” in Afghanistan as promised, with the Taliban moving new forces into place against the U.S.-supported Afghan government.

Trump’s attitude toward the military, then, is fundamentally ambivalent: He mocks the very idea of service, sacrifice, or discipline, but he likes shiny medals, big parades, and deadly weapons. He has sought to portray himself as a tough and aggressive leader who understands the military better than generals do, yet he has repeatedly sought to avoid war.

As president, he cultivated a love-hate relationship with the military. Trump initially picked leading generals as top aides, including retired Marine Gen. James Mattis as defense secretary, and former Army Lt. Gen. H.R. McMaster as national security advisor, in addition to Kelly, also a retired Marine general, at the Department of Homeland Security. Initially he called them America’s best, once calling Mattis “the closest thing to Gen. George Patton that we have, and it’s about time.” But he dismissed the same military advisors later in his first term, calling some of them “losers” and “a bunch of dopes and babies” because “we don’t win any wars anymore,” according to the book A Very Stable Genius by the Washington Post reporters Philip Rucker and Carol Leonnig. 

“This whole thing is as much about his disrespect for all types of service as about the military, but it was clear to me he saw value in claiming military bona fides,” said Michael D’Antonio, a Trump biographer.

Much of that ambivalence was also on display during Trump’s time at the military academy, which he has said in the past gave him an understanding of military service greater than that of actual veterans, as D’Antonio recounts. Trump said that his time at the New York Military Academy gave him “more training militarily than a lot of the guys that go into the military,” D’Antonio wrote in his book The Truth About Trump.

White scoffs at the notion that Trump ever had any respect for the military, and he laughed about Trump’s efforts to paint his time at the academy as a genuine military initiation. “I went into the U.S. Army during Vietnam in 1968. I served a tour in Korea,” said White, whose last name at the time he was attending the New York Military Academy was Witek. “When I got into basic training 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.”

But the academy did leave Trump with his love of superficial military grandeur, especially parades and medals. In 2016, then-candidate Trump told a supporter who gave him a copy of his Purple Heart: “I always wanted to get the Purple Heart. This was much easier.” 

“Like most ex-military, I detest his love of having parades and having real military personnel salute him,” said Alan Lapidus, a former Trump family architect, who enlisted in the military in 1957 as a combat engineer. 

Trump’s efforts at heroic self-branding also began at the academy, said White and Sandy McIntosh, another former cadet who knew Trump and his family well. Trump began wearing decorations and medals he didn’t earn, especially for academic or military achievement, and got himself placed at the head of the Columbus Day military parade in New York City as a cadet, White and McIntosh recall. “I did very well under the military system,” Trump told the Washington Post in January 2016. “I became one of the top guys at the whole school.”

His former classmates disagree. “One of the things that struck me was I don’t recall him being a good student at all,” McIntosh said. “I was two years younger than him and he asked me to go over his essays for him and improve them. It was the only time I got to see the nature of his disability. I think his grades were mostly in the D-plus or C-minus range.” 

Both White and McIntosh said the incorrigible and arrogant behavior and insubordination that had prompted Trump’s parents to send him to the military academy in the first place continued at the school. What they witnessed tends to corroborate Too Much and Never Enough: How My Family Created the World’s Most Dangerous Man, the recent family tell-all by Trump’s niece Mary Trump. She reported that Fred Trump Sr., whom she described as a “high-functioning sociopath,” helped turn his son into an entitled, self-aggrandizing narcissist whom no one could control. 

According to White, who is the same age as Trump, “my mother was confronted by Mrs. Trump on three separate occasions at the academy and what she said validates what Mary Trump wrote in that book. She cornered my mother and all she talked about was how she couldn’t control Donald and he wouldn’t listen to her. She was distraught. She pressed my mother to find a magic solution to make Donald listen.” Instead, White said, Trump regularly ignored the orders given by him and other superiors.

“The most significant incident, which I got into big trouble for, was when we were taking a picture in May of 1964, and Donald Trump refused to draw his sword. I’m the first captain and I order present arms and there are five guys behind me and they draw. But he refuses. I hear behind me, ‘Trump, draw your sword.’ Donald refuses. The picture gets taken. … He was defying a direct order, showing his defiance,” White said. “He was ‘being Trump,’ showing that his ego was more powerful than anybody’s. He later showed that picture around to show how defiant he was because he didn’t draw the sword.” 

White and McIntosh also believe that Trump inflated his grades and that his father’s influence—and deep pockets—were responsible for bumping him up from lowly supply sergeant to cadet captain in his senior year. 

“Trump was over-privileged,” White said. “His father was rich, and he was protected. His father always considered him a genius. Trump was developing this alternative reality even then, and it was allowed to flourish because he was allowed to by the school supervisors. They directly ordered me to stay away from Trump. Everybody knew Fred was pulling out his checkbook.” 

Trump’s apparent disdain for the military continues a long family tradition. His grandfather left Germany to avoid military service in the late 1800s, while his father never served. According to Mary Trump’s book, both Fred Trump Sr. and Donald Trump harshly criticized the decision by her father, the president’s older brother, Fred Trump Jr., to join the U.S. Air National Guard. Trump himself sought multiple draft deferments to avoid the Vietnam War. A number of Trump biographers have confirmed that Trump evaded the Vietnam draft, and he himself has admitted to the Washington Post, “I had a lot of deferments,” and he “always felt somewhat guilty” about avoiding service.

“Like many in his generation, he avoided serving in the Vietnam War by getting a bogus medical deferment, in his case for bone spurs, a condition widely considered permanent that somehow never interfered with his playing sports and apparently disappeared when he was no longer draft-eligible,” said another of his biographers, Gwenda Blair. “What makes Trump different is that rather than justifying this subterfuge by questioning the war’s legitimacy, he impugned the intelligence and bravery of those who did fight, calling them suckers and labelling one of the most famous veterans, John McCain, a loser because he was captured and spent more than five years in a POW camp.”

But this has always been a family affair, Blair said. “Trump was only following in the footsteps of his own grandfather,” she said. “Many decades earlier, at the end of the nineteenth century, Friedrich Trump dodged mandatory military service in Germany by emigrating to the U.S. when he was too young to serve and returning to Germany just after he turned too old.”

For classmates like White, Trump’s reported remarks are simply an echo of that long family tradition.

“It’s real simple. His grandfather dodged the draft in Germany and his father never went in. And when I came back from Korea, in 1972, I ran into him in New York City and told him where I’d been, he didn’t give a flying ripshit that I’d been to Korea. He made barfing noises,” White said. “I said, ‘Holy shit, you are a piece of work.’”