Donald Trump was demanding $400 million from Columbia University.

When he did not get his way, he stormed out of a meeting with university trustees and later publicly castigated the university president as “a dummy” and “a total moron.”

That drama dates back 25 years.

Today, these two New York City institutions — the ostentatious billionaire president of the United States and the 270-year-old Ivy League university that has cultivated 87 Nobel laureates — are locked in an extraordinary clash. The future of higher education and academic freedom dangle in the balance.

But the first battle between Mr. Trump and Columbia involved the most New York of New York prizes — a lucrative real estate deal, according to interviews with 17 real estate investors and former university administrators and insiders, as well as contemporaneous news articles.

Some former university officials are quietly wondering whether the ultimately unsuccessful property transaction sowed the seeds of Mr. Trump’s current focus on Columbia. His administration has demanded that the university turn over vast control of its policies and even curricular decisions in its effort to quell antisemitism on campus. It has also canceled federal grants and contracts at Columbia — valued at $400 million.

The Trump Organization and the White House declined to comment.

Lee C. Bollinger, the former president of Columbia who eventually opted not to pursue the property owned by Mr. Trump and foreign investors, chose instead to expand the Columbia campus on land adjacent to the university. “I wanted for Columbia a much more ambitious project than the Trump property would permit, and one that would fit with the surrounding properties, that would blend in with the Morningside campus and the Harlem community,” he said in an interview.

The clash had its roots in the late 1990s, when Columbia was facing a common challenge in New York: Situated in one of the most expensive and congested cities in the world, it wanted more space. The federal government was supercharging the budget of the National Institutes of Health, and to compete with other universities for research grants, Columbia needed room to house more scientists and labs.

Expanding its footprint beyond its Morningside Heights campus into neighboring Harlem would be complicated. In 1968, the university began construction on a gymnasium in Morningside Park. The design, construction delays and limited access to Harlem residents resulted in “cries of segregation and racism,” according to a Columbia University Libraries exhibit. Tension between the university and community leaders in Harlem persisted for decades.

Columbia officials and trustees hoped to mend the relationship, but they knew they also needed to look for alternatives.

Enter Mr. Trump. Not yet a reality television star, he was then a brash real estate developer, with a love of tabloid press attention. He offered a home for a Columbia expansion, an undeveloped property on the Upper West Side between Lincoln Center and the Hudson River. It was known as Riverside South before he rebranded it Trump Place.

The property was at the southern tip of a much larger 77-acre site Mr. Trump had owned since the early 1970s, a former freight yard that was once the largest undeveloped parcel in Manhattan. In the early 1990s, Mr. Trump had made no progress in developing the site after amassing more than $800 million in debt, most at very high interest rates, and couldn’t afford bank payments on the property.

But in 1994, two Hong Kong investors came to his rescue. They agreed to finance his vision of high-rise residences, with Mr. Trump remaining the public face of the project. He would also seek $350 million in federal subsidies.

Yet Mr. Trump was struggling to decide what to develop on the southern edge. He pursued buyers, including CBS. He boasted that the network was close to a deal for a 1.5 million-square-foot studio on the property.

But CBS eventually balked, deciding in early 1999 to stay put in its studios on West 57th Street.

A few months later, Mr. Trump was hyping the property every chance he could. “My father taught me everything I know, and he would understand what I’m about to say,” Mr. Trump said at the wake of his father, Fred Trump. Then Mr. Trump touted his plans for Trump Place. “It’s a wonderful project,” he said.

By 2000, Mr. Trump had set his sights on a new partner: Columbia, which he had heard was looking for space. A development there would have been a departure for the university. It was more than two miles from Columbia’s campus and relatively small, requiring it to be built up, with towering buildings.

Still, the idea captured the attention of several trustees and some top administrators. For more than a year, they discussed what could become of the land, mostly with officials at the Trump Organization and sometimes with Mr. Trump himself. Mr. Trump even coined a name for the potential development: “Columbia Prime.”

But in negotiations, he frequently changed his demands, even as reports would appear in Mr. Trump’s favored tabloid, The New York Post, claiming that Columbia was close to buying it.

In private, he tossed around numerous prices, topping out at $400 million, according to a Columbia official from that era, a figure that an anonymous source leaked to The Post a few times.

No matter the amount, Mr. Trump said to Columbia officials, the university would be getting such a great deal that it should also rename its business school the Donald J. Trump School of Business.

An administrator rebuffed Mr. Trump’s request. The university does rename buildings, the person told him, noting that its engineering school had been recently named for a businessman who had donated $26 million. If Mr. Trump wished to make such a gift, the person said, there were other officials at Columbia who would be eager to meet. Mr. Trump did not make a donation.

As the discussions dragged on, many people from Columbia grew frustrated with their dealings with Mr. Trump. Still, the two sides set up a meeting in a Midtown Manhattan conference room with the intention of moving a transaction forward.

A few trustees and administrators arrived with a report prepared on their behalf by a real estate team at Goldman Sachs, which attended every meeting between Columbia officials and representatives of the Trump Organization. It outlined what the investment bank considered a fair value for the land.

Mr. Trump showed up late, was informed of the university’s property analysis and became incensed.

Goldman Sachs had assigned a value in the range of $65 million to $90 million, according to a person who was in the room. In an attempt to soothe Mr. Trump, a trustee offered that the university would be willing to pay the top of the range.

It didn’t matter. A furious Mr. Trump walked out less than five minutes after the meeting had started.

The university did not formally abandon a possible expansion on Mr. Trump’s property until after Mr. Bollinger took over as president in 2002. At that time, Columbia had been considering two options: an expansion onto the Upper West Side plot or a move north into West Harlem, where Columbia had started to buy properties.

In his inaugural address, Mr. Bollinger spoke about the university’s need to expand, calling the school a “great urban university” that is the “most constrained for space.”

“This state of affairs, however, cannot last,” he added. “To fulfill our responsibilities and aspirations, Columbia must expand significantly over the next decade. Whether we expand on the property we already own on Morningside Heights, Manhattanville, or Washington Heights, or whether we pursue a design of multiple campuses in the city, or beyond, is one of the most important questions we will face in the years ahead.”

He evaluated the Trump option for a satellite campus and also began to have conversations about mending the fissure with Harlem’s community leaders, and expanding westward, creating a contiguous footprint.

He quickly determined that Harlem, not Donald Trump, was Columbia’s future. “This is an opportunity in Manhattanville to create something of immense vitality and beauty,” Mr. Bollinger told The Times in 2003. “This is not to just go in and throw up some buildings.”

Mr. Trump’s West Side property was eventually developed after the Hong Kong billionaires who owned a majority stake in it sold the entire site for $1.76 billion.

Yet Mr. Trump was outraged. He accused the investors of selling it for far less than what he could have. He sued them for $1 billion in damages. The case was dismissed, with the judge pointing out that the development had sold for $188 million more than its latest appraisal.

If he was underwhelmed by the success of the Riverside South, Mr. Trump had another asset that was appreciating: his own fame.

“The Apprentice” made its television debut in January 2004, and became an instant hit.

But Mr. Trump’s mega-stardom did not make him forget about the failed deal with Columbia.

In 2010 — about eight years after Mr. Bollinger contacted Mr. Trump to tell him the school would be expanding into Harlem — two Columbia student journalists who had written a profile of the university president received in the mail a gold-embossed letter on thick paperstock from a displeased reader, Donald J. Trump.

He included a copy of a missive he had recently sent to Columbia’s board of trustees, in which he called the Manhattanville campus “lousy” and Mr. Bollinger “a dummy.”

“Columbia Prime was a great idea thought of by a great man, which ultimately fizzled due to poor leadership at Columbia,” Mr. Trump wrote.

He signed it with a black marker and scribbled, “Bollinger is terrible!”

Mr. Trump also shared his indignation in an interview with The Wall Street Journal. “Years after the deal fell through,” the newspaper said, “Trump is still irate. ‘They could have had a beautiful campus, right behind Lincoln Center,’” Mr. Trump told the reporter and called Mr. Bollinger a “total moron.”

Mr. Trump was perhaps staying true to principles outlined in “How To Get Rich,” an advice book he co-wrote a few years after his deal with Columbia went sour.

One chapter is titled “Sometimes You Have to Hold a Grudge.”

Maggie Haberman contributed reporting.

Well before political leaders were taking action against cellphones in the classroom, the superintendent of schools in Schoharie, N.Y., a rural district about 40 miles west of Albany, was well along on his crusade against Big Tech’s commandeering of the adolescent mind. By the beginning of the school year in 2022, David Blanchard, who had been appointed as superintendent seven years earlier, had implemented a bell-to-bell policy. This meant that students could not use phones (or smart watches or earbuds) at any point during the school day — not during lunch or study halls or periods of transition from one class to another.

The effort certainly seemed extreme. This was before Jonathan Haidt’s book “The Anxious Generation” spurred consensus about the destructive impact phones were having on teenage mental health, before the former surgeon general’s call for warning labels on social media platforms. Mr. Blanchard was troubled by all the disconnection he was seeing. His experiment yielded benefits right away.

“We found a transformative environment,” he told me recently. “We expected kids to be in tears, breaking down. Immediately we saw them talking to each other, engaged in conversation in the lunchroom.”

One unanticipated outcome was that students flooded counselors’ offices looking for help on how to resolve conflicts that were now happening in person. Previously, if they found themselves in some sort of fight with someone online, they would have called or texted a parent for advice on how to deal with it, Mr. Blanchard told me. “Now students were realizing that their friends were right there in front of them and not the people on social, a few towns away, that they had never met.” Enrollment in elective classes also went up when the option to scroll your way through a 40-minute free period was eliminated.

The success in Schoharie has been a showpiece in Gov. Kathy Hochul’s recent campaign to ban cellphones in schools across New York. At least eight other states, including Florida and Louisiana, have instituted restrictions of varying kinds. In September, Gov. Gavin Newsom signed the Phone-Free School Act requiring every school district in California to devise a policy limiting the use of smartphones by July 2026. This week a suggested cellphone ban was the subject of a public hearing in the Texas State Legislature, where a bill was introduced with bipartisan support a few months ago by a young member of the House who lamented that she had been “born into these devices.”

Governor Hochul’s proposal follows the Schoharie bell-to-bell approach. In a rare instance of agreement between labor and government, it is supported by the United Federation of Teachers, the union representing New York City schoolteachers. As Michael Mulgrew, the president of the U.F.T., put it, “It is simple, and everyone knows what the expectation is.”

Still, the proposal’s all-constraining formulation has not made it an obvious or easy sell. Introduced in January as part of the state’s current budget negotiations, it is opposed by some groups like the state’s School Boards Association. These groups favor an alternate strategy coming out of the statehouse that endorses the notion that local jurisdictions ought to have say in how policy limiting phone use is devised.

Studies comparing students with and without cellphones in classrooms generally show better academic performance among those without. The advantage of keeping devices out of students’ hands for the entire day is that it both reduces the time teachers have to waste policing phone use and also minimizes the possibility that whatever erupts on Snapchat during lunchtime will kill any chance of paying attention to the “Moby-Dick” discussion in the afternoon. In Schoharie, students put their smartphones in a pouch with a magnetic lock — the kind used in stores to prevent theft — which cannot be opened until a school attendant releases them at the end of the day.

In recent years, parents around the country have demanded more and more control over what their children are reading and doing in school. The constituents most opposed to all-day phone bans are the mothers and fathers who seem to be addicted to constant filial contact. Governor Hochul has spoken to aggrieved first-grade teachers who told her that they are overseeing classrooms full of children wearing smart watches. “Mommy and Daddy were checking in all day long saying, ‘I miss you and can’t wait to see you,’” the governor told me. “That’s a parental need,” she said, “not a student need.” The continuation of these patterns, she worried, was bound to keep children from emerging as fully functioning adults.

It is the sadly all too reasonable fear of many parents that something catastrophic could happen at school without their being able to reach their children. It is a fantasy that communication would save them. Throughout the rollout of the proposal, the governor’s office has had law enforcement come in and speak with school groups to explain how misguided a notion that is. In an emergency, phones distract children from remaining focused on whomever has been entrusted to keep them safe; calls and texts create added panic.

Should the governor’s proposal pass, it would take effect in September. Parents in Schoharie were quite resistant to the ban at first, Mr. Blanchard told me. But they came around when they realized that with the addiction broken, it became much easier to manage their children’s digital lives at home — and much more gratifying to see them engage with the world without staring at their hands.

Yeshiva University said on Thursday that it would recognize an L.G.B.T.Q. student club on campus, bringing to an end a bitter yearslong legal battle over whether the school could deny the group official recognition on religious grounds.

Yeshiva, a Modern Orthodox Jewish institution with campuses in Manhattan and the Bronx, had refused for years to recognize the club, which had been known as the Yeshiva University Pride Alliance. The case made its way through state and federal courts, even reaching the U.S. Supreme Court, and was closely watched by religious organizations and religious freedom groups.

But on Thursday, its administration said in a statement that it and the students had “reached an agreement, and the litigation is ending.” As part of the settlement, the students said the Pride Alliance would be renamed Hareni, a religious term they had suggested.

In a statement, the school said the club “will seek to support L.G.B.T.Q. students and their allies and will operate in accordance with the approved guidelines of Yeshiva University’s senior rabbis.”

It added: “The club will be run like other clubs on campus, all in the spirit of a collaborative and mutually supportive campus culture.”

The battle at Yeshiva University had brought one of the country’s most liberal cities to the front line of a nationwide debate over religious freedom and civil rights and whether houses of worship, religiously affiliated organizations or even pious individuals could be compelled to provide public accommodations to people with differing views.

Yeshiva’s decision came at a time when L.G.B.T.Q. rights appear under threat across the country from the Trump administration, which has fiercely attacked elite universities and mounted a campaign against the participation of transgender people, in particular, in public life.

Throughout years of legal wrangling, the school took sometimes extreme steps to deny the club official recognition, including imposing a brief ban on all on-campus clubs. The dispute drew the attention of state lawmakers, who criticized the university’s position and suggested it might have imperiled its ability to access public funds.

The announcement on Thursday represented a notable reversal for Yeshiva, which did not explain why it decided to change its approach.

In a statement, Hanan Eisenman, a university spokesman, said that the students who filed the lawsuit had actually agreed to a proposal Yeshiva made in 2022, when administrators surprised the students by forming a club “grounded” in Jewish religious law that they called “an approved traditional Orthodox alternative to YU Pride Alliance.”

“Our students’ well-being is always our primary concern,” he said. “We are pleased that our current undergraduate students will be leading the club announced today which is the same club approved by our senior rabbis two and a half years ago.”

But Zak Sawyer, a spokesman for the plaintiffs, said the settlement went far beyond what Yeshiva proposed in 2022, which he said “was created without student input, had no members, held no events and never existed outside of a press release.”

“Hareni has secured written guarantees ensuring it has the same rights and privileges as other student clubs, including access to campus spaces, official student event calendars and the ability to use ‘L.G.B.T.Q.’ in its public materials — none of which existed under YU’s prior ‘initiative,’” he said.

In interviews, members of the new club said they hoped the settlement would ensure that L.G.B.T.Q. students felt valued.

“I think this will really show to other people that there is no separation between being queer and being a Jew and that you are allowed to be a queer Jew on campus at Yeshiva University,” said Hayley Goldberg, 21, one of the club’s co-presidents.

Indeed, Ms. Goldberg and Schneur Friedman, 22, another co-president, said the club’s new name emphasized the importance of Judaism in their lives.

It was taken from a phrase recited before prayer, which they thought had special meaning for L.G.B.T.Q. acceptance: “I hereby take upon myself to fulfill the commandment of loving your fellow as yourself.”

The university’s administration had for years rejected student demands to recognize an L.G.B.T.Q. club because it said doing so would conflict with Orthodox Jewish religious teaching. While many Jewish congregations support L.G.B.T.Q. rights, many Orthodox leaders interpret the Torah as promoting traditional ideas of gender and sexuality.

After a group of students and alumni sued Yeshiva in 2021, its administration argued in court that its refusal was legally protected because it was exempt from New York’s civil rights laws as a Jewish religious institution.

Religious exemptions to such laws are common, but in recent years have increasingly been used to deny equal treatment to L.G.B.T.Q. people.

Yeshiva is structured as a modern American university with graduate programs in law and business that enroll many non-Jewish students. The university is home to roughly 6,000 students on four campuses in Manhattan and the Bronx.

Critics of the school’s legal argument that it was a religious institution said Yeshiva had more in common with religiously affiliated colleges and universities, like Fordham or Notre Dame, than it did with Christian seminaries, which are exempt from nondiscrimination laws because they train priests.

Judges in New York rejected the university’s religious freedom arguments, which led the school to file an unusual emergency stay to the Supreme Court in 2022. The court ruled in a 5- to-4 decision that Yeshiva must abide by lower court rulings and pursue any challenges in state court before it appealed to the Supreme Court.

Mr. Friedman said the university had approved a number of events that the club could host, including movie nights, panel discussions and holiday events.

But it declined to specify what sort of activities might not be approved. Still, Mr. Friedman described Thursday’s agreement as “a massive step.”

“The fact that this is happening very much within the guidelines of Yeshiva is significant,” said Mr. Friedman.

“If this can happen here, it has wider implication for the Orthodox Jewish community as a whole,” he said. “Even if there are compromises, it has a wide effect, which is very exciting.”