Trump’s Decades of Testimony Provide Some Clues about How He’ll Fight for His Real Estate Empire

AP Photo/Seth Wenig, Pool
Former President Donald Trump, center, flanked by his defense attorneys, Alina Habba, left, and Chris Kiss, waits for the continuation of his civil business fraud trial at New York Supreme Court, Oct. 25, 2023, in New York.

NEW YORK (AP) — Donald Trump has testified in court as a football owner, casino builder and airline buyer. He bragged in a deposition that he saved “millions of lives” by deterring nuclear war as president. Another time, he fretted about the dangers of flung fruit.

Conditioned by decades of trials and legal disputes, Trump is now poised to reprise his role as witness under extraordinary circumstances: as a former Republican president fighting to save the real estate empire that vaulted him to stardom and the White House.

Trump is set to testify Monday at his New York civil fraud trial, taking the stand in a deeply personal matter that is central his image as a successful businessman and threatens to cost him control of marquee properties such as Trump Tower. His highly anticipated testimony in the trial of New York Attorney General Letitia James’ lawsuit follows that of his eldest sons, Trump Organization executives Eric and Donald Trump Jr., who testified last week. His eldest daughter, Ivanka, is set to testify on Wednesday.

As court ended Friday, a state lawyer teased the former president’s appearance. Asked who would be testifying Monday, Andrew Amer told the judge: “The only witness will be Donald J. Trump.”

Trump has testified in court in at least eight trials since 1986, according to an Associated Press review of court records and news coverage. He also has been questioned under oath in more than a dozen depositions and regulatory hearings.

In 1985, he was called to testify before Congress as owner of the USFL’s New Jersey Generals and he testified on behalf of lawyer and friend Roy Cohn at a state disciplinary hearing that led to Cohn’s disbarment. In an early flash of his firebrand persona, in 1986, Trump told New Jersey’s casino commission that plans for highway overpasses near one of his casinos “would be a disaster. It would be a catastrophe.”

Those testimonies, captured in thousands of pages of transcripts and some on videotape, offer clues to the approach Trump is likely to take when he testifies in Manhattan.

They show clear parallels between Trump as a witness and Trump as a president and current candidate for the office. His rhetorical style in legal proceedings over the years bears echoes of his political verve: a mix of ego, charm, defensiveness, aggressiveness, sharp language and deflection. He has been combative and boastful, but sometimes vague and prone to hedging or being dismissive.

Testifying in the USFL’s antitrust lawsuit against the NFL in 1986, Trump denounced allegations that he had spied on NFL officials at one of his hotels, calling the claim “such a false interpretation it’s disgusting.”

In 1988, as he sought to buy Eastern Air Lines’ Northeast shuttle service, Trump turned on the charisma, flashing a wide smile at the judge’s female law clerks and shaking hands with the bailiff during a break in his testimony at a federal court hearing in Washington. Trump testified that his $365 million purchase, later approved, would be a “major boost in morale” for employees.

On the stand in a boxing-related case in 1990, Trump described a Mike Tyson fight he planned for one of his casinos in Atlantic City, New Jersey, as “one of the greatest rematches you could have.” Accused by two men of cutting them out of a riverboat gambling project, Trump professed ignorance, testifying in 1999: “I was shocked by this whole case. I had no idea who these people were.”

Trump was briefly called to the witness stand in the New York case last month to explain comments outside of court that the judge said violated a limited gag order.

Before that, he last testified in a courtroom in 2013, two years before launching his winning presidential campaign. An 87-year-old suburban Chicago widower had sued him over changes to contract terms for a hotel and condominium tower she had bought units in as an investment. Trump grew increasingly agitated as his testimony wore on, at one point raising his arms and bellowing: “And then she sued me. It’s unbelievable!”

Chicago lawyer Shelly Kulwin cross-examined Trump on behalf of the plaintiff, Jacqueline Goldberg. He said the tenor of Trump’s testimony inside the federal courthouse in Chicago echoed the bruising ebb and flow later seen at campaign rallies and on TV.

His demeanor was calm at first, and then argumentative, defensive, off-topic, speechmaking. Exactly what he does today, Kulwin said in an interview.

Based on my experience with him, you better be able to have super tight questions, with documents to support them, so that he cannot wiggle around, Kulwin added. “I would approach the judge and have him admonished before he even got on the stand: ‘Mr. Trump, this is not a political campaign. These people, you’re not trying to get their vote. This is a judicial proceeding.'”

Goldberg lost to Trump but said she did not regret suing him, testifying: “Somebody had to stand up to him.” She died in August at age 97.

Trump has attended seven days of the New York trial, quietly studying witnesses from the defense table while also lashing out at the case, the judge and state lawyers in front of TV cameras in the hallway. He’s called the case a “sham,” a “scam,” and “a continuation of the single greatest witch hunt of all time.”

Opining about the case on social media, he thrills in what he calls the trial’s “Perry Mason” moments — testimony and arguments he feels have helped his side — as he pays homage to the classic TV courtroom drama.

In 1990, Trump testified in a losing effort in a lawsuit over his company’s failure to make pension contributions on behalf of about 200 undocumented Polish workers hired to tear down a building to make way for Trump Tower. A year later, he was in court again in Manhattan, testifying against a man who claimed he had a contract to develop Trump’s board game and was owed 25% of profits from “Trump: The Game.”

Trump won that one and another lawsuit in 2005, where he testified that a construction company had “fleeced” him by overcharging him by $1.5 million for work at a golf course in New York’s Westchester County.

Trump’s current New York trial hinges in part on how much he and other Trump Organization executives were involved in valuing his properties and calculating his wealth for the annual financial statements that were given to banks, insurers and others to make deals and secure financing.

James alleges the statements inflated Trump’s net worth by billions of dollars, making him appear to lenders as a more worthy credit risk and allowing him to obtain better interest and insurance rates. Trump has denied wrongdoing.

Eric and Donald Trump Jr. testified that they relied on an outside accounting firm and the Trump Organization’s finance team to prepare the statements and that they assumed those statements were accurate.

Trump testified in a deposition in a case in April that he never felt his financial statements “would be taken very seriously,” and that a disclaimer on them warned people doing business with him to do their own homework.

He insisted the banks that James alleges were snookered with lofty valuations suffered no harm, got paid in his deals and “to this day have no complaints.” Trump decried the lawsuit as a “terrible thing,” telling James and her staff “you don’t have a case.”

Before the trial, the judge ruled that the statements were fraudulent. He set in motion punishment that shifts control of some Trump companies to a court-appointed receiver. An appeals court has put that on hold, for now.

The nonjury trial, now into its second month, concerns allegations of conspiracy, insurance fraud and falsifying business records. James, who is suing Trump, his company and top executives, including his eldest sons, is seeking $250 million in penalties and a ban on the defendants doing business in New York.

When questioned in the past about his business and financial dealings, Trump has sometimes deflected responsibility and blame. In a 2013 deposition over a failed Florida condominium project, Trump blamed an employee for paperwork that said he was developing a project when, in reality, he wasn’t.

I have a woman that does it, he said. He then started parsing the wording at issue, saying: “But you know, developing, the word develop, it can be used in a lot of different contexts.”

Another refrain in Trump’s depositions is his incredulity that he would be taken so seriously for hyping up his real estate projects.

You always want to put the best possible spin on a property that you can, Trump said in a December 2007 deposition in his lawsuit against a journalist he had accused of playing down Trump’s wealth. “No different than any other real estate developer, no different than any other businessman, no different than any politician.”

Trump’s penchant for puffery is sure to come up on Monday. He and his company are accused of inflating his property values and using a variety of methods to maximize the results. For years, he even listed his Trump Tower penthouse in Manhattan as being three times its actual size. He now claims his financial statements undersold his wealth and that his Mar-a-Lago resort in Florida is worth more than $1 billion.

Trump is portraying the civil fraud case and his four criminal cases as prongs of political persecution designed to impede his candidacy as the 2024 Republican front-runner for president. He has referenced his political standing in prior legal settings, including during a 2016 deposition when he noted, unprompted, how he had defeated his Republican primary opponents.

I obviously have credibility because I now, as it turns out, became the Republican nominee running against, we have a total of 17 people that were mostly senators and governors, highly respected people. So it’s not like, you know, like I’ve said anything that could be so bad, he said.

In his April deposition, Trump soberly described the presidency as the “most important job in the world” before bragging about saving lives by preventing North Korean dictator Kim Jong Un from launching a nuclear attack.

In an October 2021 deposition, Trump waxed about weapons of a different sort, warning of the dangers posed by tomatoes and other fruit, which he feared would be thrown at him on the campaign stage.

You get hit with fruit it’s — no, it’s very violent stuff, he said. Trump was testifying in connection to a lawsuit filed by a group of protesters who said they were roughed up by Trump’s private security guards when he was running in 2015.

Trump had been asked about a rally in which he told the crowd: “If you see someone getting ready to throw a tomato, just knock the crap out of them, would you.”

It was said sort of in jest. Buy maybe, you know, a little truth to it, Trump said of his remarks.

It’s very dangerous stuff. You can get killed with those things, he warned. “I wanted to have people be ready because we were put on alert that they were going to do fruit. And some fruit is a lot worse than — tomatoes are bad by the way. But it’s very dangerous.”