Trump’s Historic Fury at Columbia Over $400 Million: Does This Ring a Bell?

Donald Trump was asking for $400 million from Columbia University.

When his demands were not met, he left a meeting with the university’s trustees in a huff and later publicly lambasted the university president, calling him “a dummy” and “a total moron.”

This saga goes back 25 years.

Currently, these two notable New York City entities — the flamboyant billionaire president of the United States and the 270-year-old Ivy League institution that has produced 87 Nobel laureates — find themselves in a remarkable confrontation. The fate of higher education and academic liberty hangs in the balance.

However, the initial conflict between Mr. Trump and Columbia revolved around a quintessentially New York prize — a lucrative real estate deal, based on interviews with 17 real estate investors and former university officials, along with contemporary media reports.

Some former university officials now ponder whether the eventually unsuccessful property deal planted the seeds for Mr. Trump’s ongoing scrutiny of Columbia. His administration is pressuring the university to cede significant control over its policies, including curricular matters, as part of its efforts to combat antisemitism on campus. Additionally, it has revoked federal grants and contracts to Columbia—totaling $400 million.

The Trump Organization and the White House opted not to comment.

Lee C. Bollinger, the former president of Columbia who ultimately chose not to pursue the property owned by Mr. Trump and foreign investors, instead decided to expand the Columbia campus on adjacent land. “I envisioned a much more ambitious project for Columbia than what the Trump property would allow, one that would integrate with the surrounding environment and blend seamlessly into the Morningside campus and the Harlem community,” he stated in an interview.

The conflict has roots in the late 1990s when Columbia faced a familiar predicament in New York: as one of the most expensive and congested cities globally, it sought additional space. With the federal government significantly increasing funding for the National Institutes of Health, Columbia needed more facilities to attract scientists and laboratories for research grants.

Expanding beyond its Morningside Heights campus into neighboring Harlem posed challenges. In 1968, the university began building a gymnasium near Morningside Park. According to a Columbia University Libraries exhibit, design issues, construction delays, and restricted access for Harlem residents led to decades of tension, labeled as “cries of segregation and racism.”

Columbia officials and trustees aimed to heal their relationship with the community but recognized the need for alternatives.

Then came Mr. Trump. Before becoming a reality television personality, he was a bold real estate developer, eager to attract tabloid attention. He proposed an undeveloped property on the Upper West Side, situated between Lincoln Center and the Hudson River, as a potential site for Columbia’s expansion. It was known as Riverside South before he rebranded it as Trump Place.

This property was at the southern end of a much larger 77-acre parcel Mr. Trump had owned since the early 1970s, which had once been the largest undeveloped site in Manhattan, previously a freight yard. By the early 1990s, he had made little headway with its development after accumulating over $800 million in debt, mostly at exorbitant interest rates, making it hard to meet bank obligations.

In 1994, two Hong Kong investors came to his aid. They agreed to fund his vision for high-rise residences, with Mr. Trump as the project’s public face while he sought $350 million in federal subsidies.

However, Mr. Trump struggled to finalize plans for development on the southern edge. He sought buyers, including CBS, boasting that the network was on the verge of a deal for a 1.5 million-square-foot studio at the site.

Ultimately, CBS opted to remain in its West 57th Street studios in early 1999, leading Mr. Trump to promote the property at every opportunity. “My father taught me everything I know, and he would certainly understand what I’m about to say,” he remarked at his father Fred Trump’s wake, proceeding to highlight his plans for Trump Place. “It’s a magnificent project,” he asserted.

By 2000, Mr. Trump turned his attention to Columbia as a potential new partner, having learned they were in search of additional space. A development there would have represented a significant shift for the university, positioned over two miles from its main campus and relatively compact, requiring substantial construction to accommodate towers.

Despite this, the concept captured the interest of several trustees and top administrators. For over a year, they deliberated on the potential of the land, mainly with officials from the Trump Organization and sometimes with Mr. Trump personally. Mr. Trump even coined a name for the possible development: “Columbia Prime.”

However, throughout negotiations, he frequently revised his demands, despite tabloid reports, particularly from the New York Post, asserting that Columbia was nearing a deal.

In private discussions, he floated multiple price points, maxing out at $400 million, according to a former Columbia official from that time, a figure that was leaked to The Post by an unnamed source several times.

Regardless of the sum, Mr. Trump insisted that the university was getting such a tremendous bargain that it should rename its business school to the Donald J. Trump School of Business.

An administrator rejected Mr. Trump’s proposition. While the university does rename facilities, the individual pointed out that they had recently named an engineering school after a businessman who donated $26 million. If Mr. Trump wished to contribute in a similar fashion, they had other officials at Columbia who would be delighted to meet him. Mr. Trump made no such donation.

As talks continued, frustration grew among many at Columbia regarding their interactions with Mr. Trump. Nevertheless, the two parties arranged a meeting in a Midtown Manhattan conference room aimed at advancing the transaction.

A few trustees and administrators were present with a report drafted on their behalf by a real estate team from Goldman Sachs, which was involved in every meeting between Columbia representatives and the Trump Organization. The report delineated what the investment bank deemed a fair valuation for the land.

Mr. Trump arrived late, learned of the university’s property analysis, and became furious.

Goldman Sachs had assigned a valuation between $65 million and $90 million, according to someone present in the room. In a bid to placate Mr. Trump, a trustee suggested that the university would be willing to pay up to the higher end of that range.

However, it made no difference. A livid Mr. Trump left less than five minutes into the meeting.

It wasn’t until Mr. Bollinger became president in 2002 that the university formally abandoned the idea of expanding onto Mr. Trump’s property. By that time, Columbia had been considering two choices: an expansion onto the Upper West Side site or a move north into West Harlem, where it had begun purchasing properties.

In his inaugural address, Mr. Bollinger reflected on the university’s need to grow, describing Columbia as a “great urban university” that was “most constrained for space.”

“This situation, however, cannot persist,” he remarked. “To meet our responsibilities and aspirations, Columbia must significantly expand over the next decade. Whether we grow on the properties we already control in Morningside Heights, Manhattanville, or Washington Heights, or whether we contemplate multiple campuses throughout the city or beyond, remains one of the primary challenges we will face in the coming years.”

He assessed the Trump option for a satellite campus while also beginning dialogues to repair the relationship with Harlem’s community leaders and expand westward, thereby creating a contiguous footprint.

Ultimately, he concluded that Harlem, not Donald Trump, represented Columbia’s future. “This is an opportunity in Manhattanville to establish something of immense vitality and beauty,” Mr. Bollinger commented to The Times in 2003. “The aim is not merely to come in and erect some buildings.”

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

Nonetheless, Mr. Trump was infuriated. He alleged that the investors had sold it for far less than he could have achieved. He filed a lawsuit for $1 billion in damages, which was dismissed by the judge who noted that the development had actually sold for $188 million more than its latest appraisal.

If he was dissatisfied with the fortunes of Riverside South, Mr. Trump had another asset rising in value: his own celebrity.

“The Apprentice” debuted on television in January 2004, quickly becoming a sensation.

However, Mr. Trump’s meteoric rise to fame didn’t erase his memory of the fallen deal with Columbia.

In 2010 — around eight years after Mr. Bollinger informed Mr. Trump that the university would expand into Harlem — two Columbia student journalists who had profiled the university’s president received a gold-embossed letter on high-quality paper from an irate recipient, Donald J. Trump.

He enclosed a copy of a letter he had sent to Columbia’s board of trustees, criticizing the Manhattanville campus as “lousy” and labeling Mr. Bollinger “a dummy.”

“Columbia Prime was a brilliant idea conceived by a great man, which ultimately fell flat due to subpar leadership at Columbia,” Mr. Trump wrote.

He signed it in black marker, adding, “Bollinger is terrible!”

Mr. Trump also expressed his frustration during an interview with The Wall Street Journal. “Years after the deal collapsed,” the newspaper reported, “Trump remains furious. ‘They could have had a stunning campus, right behind Lincoln Center,’” Mr. Trump told the reporter, again calling Mr. Bollinger a “total moron.”

Mr. Trump may have been adhering to principles laid out in “How To Get Rich,” an advisory book he co-wrote shortly after the Columbia deal soured.

Maggie Haberman contributed reporting.