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Long before Donald J. Trump came one election away from becoming the most powerful man on Earth, he played at being the most powerful man at P.S. 70 in the Bronx.

Memories of Trump’s tone-deaf “Principal for a Day” performance at the poor New York City elementary school — where he offered to buy a select group of kids Nike sneakers and was promptly challenged by one little boy who wanted a scholarship instead — have bubbled back up with new meaning for several key players who were there that spring day in 1997.

Trump, who may soon be affecting education policy for every child in America, had been recruited by the nonprofit Public Education Needs Civic Involvement in Learning (PENCIL), which brings influential New Yorkers into the public schools to create personal connections. While the Republican nominee for president likely doesn’t remember the educators he met that day in an outer-borough school, P.S. 70 staff members and others involved tell The 74 it was a cringeworthy episode they’ll never forget.

Sylvia Simon, the real principal of P.S. 70 at the time, said as an African American who was herself a product of New York City public schools, her student’s offense at Trump’s sneaker lottery resonated on a deeply personal level.

“I’m a minority woman, I come from the South Bronx from the same neighborhood; to me, I thought it was disrespectful,” she said, adding, “I would have preferred that he gave the money that those sneakers cost to the (school).” 

Simon, now retired and living in Westchester County, can still summon the disappointment she and her students felt after Trump showed up in his limousine, spent about two hours at the school and left. She compared it to a visit by a Scholastic publishing executive who took the time to ask about P.S. 70’s demographics, noted that most of the students were on free and reduced-price lunch, and ended up donating books to every grade for a year.

“It’s not that you live well, and you live in a nice environment and you have made lots of money. It’s the ability to put yourself in [another’s] place. I hope [Trump has] learned to do that.

“I’m not so sure that he — he didn’t understand, to give low-income kids a lottery for sneakers was an insult. But hopefully he’s learned … it was a long time ago.”

Former Assistant Principal Mark Singer recalls that when he took Trump on a tour of the building, the known germophobe plucked a tissue out of his pocket to protect his hand from touching the school stairwell railing.

Everyone escorting the billionaire noticed, Singer says, but no one said a word.

David MacEnulty, who ran a celebrated chess program at P.S. 70 and now teaches chess at Manhattan’s exclusive Dalton School, also was up close to Trump that day.

“The thing that it really left me with was that this man had absolutely no clue about education,” he said. “He certainly had no clue where he was and who he was working with, and I just got the impression that this is a guy who shoots from the hip and whatever’s on his mind at the moment is what’s going to come out. I’d like for somebody to be a little more thoughtful.”

MacEnulty at the time was trying to scrape together enough money to get his chess champions to a national tournament in Tennessee.

“Donald Trump showed up and gave the people behind the counter a fake million dollar bill as his donation,” MacEnulty said. “And then he took that back and gave them an actual $200, which is kind of slim.”

Trump’s campaign spokesperson Hope Hicks declined to comment on his P.S. 70 visit when reached on the phone Sunday.

Eric Nadelstern, a former Bronx superintendent and deputy New York City schools chancellor, remembered reading about Trump’s visit in the paper and talking about it with colleagues — it was such an outlandish gesture, he said, for anyone walking into a public school that it bordered on comical.

“I thought it validated the wisdom of our kids and made Trump look foolish. ‘I’ll give every kid a pair of Nikes’ is such a superficial understanding of what they need, it’s even a superficial understanding of what they want,” said Nadelstern, who now teaches at Columbia University. “They want to succeed, they don’t want to be relegated to second-class citizenship, and they know that school is their ticket to success, that there’s nothing else available to them to get them out of their neighborhood, to get out of poverty, often homelessness.”

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The real estate mogul was among some 1,000 celebrities, business titans and civic leaders — including Johnnie Cochran and Tipper Gore — who had been persuaded that day by PENCIL to serve as acting principal of a public school. The goal of the annual event was to foster relationships between city schools and those in the private sector with the financial resources and know-how to help them.

Volunteer principals at other city schools had donated computers, funded trips, launched a music education program and, in one case, became an ongoing advisor to the principal and then sponsor of a student internship program. But none got quite the level of attention that Trump did.

“As you’ve seen in this presidential campaign, wherever Donald Trump goes, the media goes. So we recruited him and the outcome was very surprising to us,” said Ruth Cohen, who had just started working at PENCIL back then and went on to serve as president from 1998 to 2004. She is now a director of education programs at the American Museum of Natural History.

“Normally publicity like that story would sting an effort like ours because it would show that it’s, you know, dilettantish, but, in fact, it showed what is true and good about the kids that we’re trying to help,” Cohen said.

Learning that fifth-grader Andres Rodriguez, 11, whose father was dead and whose mother couldn’t work because of a bad leg, questioned Trump on his sneakers largesse, Cohen said, she felt a surge of pride for the student and recalled thinking, “‘You go, kid!’”

MacEnulty, the chess teacher, remembers Trump being stumped by Rodriguez.

“Trump finally said, ‘I don’t have an answer.’ That’s a direct quote,” MacEnulty said.

The morning the story hit the New York papers, Trump called to summon PENCIL’s executive director Lisa Belzberg to an 8 a.m. breakfast meeting the next day at The Plaza Hotel, the landmark Trump had sold to Saudi and Asian investors two years before.

A senior PENCIL employee at the time who was familiar with the meeting recalled the encounter for The 74, saying that after glad-handing his way through the room, Trump sat down, kissed Belzberg, and congratulated himself on a job well done.

“How great am I? How great was that? Front page of the Metropolitan section … do I work for you or not? Do I put you on the map? Aren’t we great?”

Belzberg — who had told the New York Times that when the Principal for a Day isn’t a celebrity of Trump’s wattage, “there’s real substance that goes on” — reportedly unleashed on him at the breakfast table.

Didn’t Trump get how boorishly he had behaved at the school?

Did he realize that he’d created a public relations nightmare for the organization?

Belzberg reportedly told Trump she would await his checks for both P.S. 70 and PENCIL. None were forthcoming.

Trump did, in fact, arrange for some P.S. 70 students and their parents to take buses from the school to the Nike store on East 57th Street in the Trump Tower to follow through on his promise, MacEnulty said. Ironically it was a P.S. 70 alumna living in Florida who read the New York Times story about the fake million dollars and called MacEnulty, making a $5,000 donation to the chess team that was the first of many.

Charles Bendit, who recently stepped down from the New York State Board of Regents, was another New York real estate developer who first got involved with PENCIL in the 1990s.  Bendit’s few stints as Principal for a Day grew into a decade-long partnership with Harry S. Truman High School in the Bronx and its principal, Sana Nasser.

He also created a student internship program at his real estate company, Taconic Investment Partners, which has since offered hundreds of New York City students the chance to work (and get paid) while still in high school.

“Donald is a bit of a showman and he did his thing,” said Bendit, a PENCIL board member for a decade and currently a vice chairman. “He did his Donald thing, but I give him credit for actually taking an interest and spending the time that he spent.”

“That’s not me … and that’s who he is,” he added. “And I hope that his education policies, (that) he takes it a lot more seriously than he might have taken it in 1997.”

Have a memory of Donald Trump you’d like to share? Email us here, or sign up for our newsletter. And follow The 74’s campaign coverage — including our exclusive education interviews with candidates — at #EDlection2016. 

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This article was published in partnership with The74Million.org.