Decades Ago, Columbia Refused to Pay Trump $400 Million. Note That Number.

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.