Trump’s History of Depositions Offers Insights Into His Upcoming Legal Battle for His Property Dynasty

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Over the years, Donald Trump has been deposed as a sports team owner, ambitious casino developer, and prospective airline purchaser. He has claimed in a deposition that his presidency averted nuclear war, boasting of saving “millions of lives.” He has also expressed concern over the potential hazards of airborne fruit.

With a long history of legal confrontations, Trump is about to take the witness stand under extraordinary circumstances: as a past Republican president embattled to protect the property empire that propelled him into fame and ultimately, the presidency.

Trump is scheduled to take the witness stand on Monday in his civil fraud trial in New York, defending against claims that could undermine his renowned business acumen and jeopardize his hold on signature assets like Trump Tower. His testimony, a focal point of the trial initiated by New York Attorney General Letitia James, comes on the heels of his two oldest sons, Trump Organization executives Eric and Donald Trump Jr., who took the stand the preceding week. Ivanka Trump, his daughter, is expected to testify the following Wednesday.

At the close of the court session on Friday, the anticipation of Trump’s appearance was palpable. State attorney Andrew Amer, when questioned about the forthcoming witness, confirmed to the presiding judge, “The sole witness will be Donald J. Trump.”

Trump has been a witness in a minimum of eight trials since 1986, as established by a Big Big News examination of judicial records and media reports. Additionally, he has been subject to questioning under oath in numerous depositions and regulatory proceedings.

In 1985, as the USFL’s New Jersey Generals owner, he testified before Congress and defended his lawyer and confidant Roy Cohn during a state disciplinary hearing that resulted in Cohn’s disbarment. In a memorable display of his combative style in 1986, Trump warned New Jersey’s casino commission about the dire consequences of proposed highway overpasses near his casino, labeling the idea “a disaster.”

These earlier testimonies, preserved across thousands of pages and some on video, give a glimpse into the approach Trump might adopt in his upcoming Manhattan testimony.

His manner in these legal settings seems to mirror his time in the Oval Office and his current political endeavors. His legal rhetoric over the years is reminiscent of his political fervor: a fusion of boastfulness, charm, defensiveness, and aggression, often marked by blunt language and redirection. He’s displayed a pugnacious and proud demeanor, though at times he has been elusive, resorting to evasive or dismissive tactics.

In the 1986 USFL antitrust suit against the NFL, Trump vigorously rejected claims of espionage against NFL officials at his hotel, dismissing them as “disgusting.”

In 1988, during his attempt to acquire Eastern Air Lines’ shuttle service, he deployed his charm in court, engaging warmly with the judge’s aides and greeting court officers, touting his bid as a morale booster for the staff.

In a 1990 court case centered on boxing, Trump extolled a Mike Tyson match at one of his casinos as a highly anticipated rematch. Faced with accusations in 1999 of sidelining partners in a riverboat casino venture, he feigned shock in his testimony, claiming ignorance of the accusers’ identities.

A brief courtroom appearance in the ongoing New York case last month required Trump to clarify his previous public statements that had violated a gag order imposed by the judge.

Prior to that, his last courtroom testimony was in 2013, two years before his successful presidential bid. During this trial, an elderly investor had sued him for contract alterations on a Chicago tower investment. Trump’s patience waned during cross-examination, culminating in an outburst reflecting his disbelief at being sued.

Shelly Kulwin, who cross-examined Trump in that case, observed that Trump’s courtroom demeanor—initially composed, later confrontational—was a precursor to his public persona during political rallies and television appearances.

Kulwin advised that handling Trump required precise questioning backed by documentary evidence to prevent him from evading topics. He suggested preemptively requesting judicial instruction to remind Trump that the proceedings were judicial, not political.

Despite losing to Trump, the plaintiff in the case, Jacqueline Goldberg, stood by her decision to sue him, citing the importance of holding him accountable. Goldberg passed away in August at the age of 97.

Throughout the current New York trial, Trump has maintained a reserved presence, observing testimony while concurrently attacking the case and its participants publicly. He’s branded the lawsuit a “witch hunt,” echoing his familiar rhetoric against perceived political persecution.

Trump has taken to social media to comment on the trial, pointing to moments he perceives as favorable to his case with theatrical relish, drawing parallels to the dramatic turns in the “Perry Mason” television series.

In 1990, Trump was embroiled in a lost legal battle over unpaid pension contributions for Polish workers involved in constructing Trump Tower. The following year, he testified over the sale of two condominiums, which included disputes over marble bathrooms and a kitchen equipped with a ‘pot-scrubber.’

The upcoming trial could prove a pivotal moment for Trump, one that may reverberate beyond the courtroom and into his public and political standing. How he handles himself under the scrutiny of the court may lend significant insight into his approach to current and future legal and political battles.

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More about Trump Legal Testimony

• Trump’s Testimony Tactics
• Trump Organization Financial Practices
• New York Fraud Trial Developments
• Eric and Donald Trump Jr. Testimonies
• Potential Legal Outcomes for Trump
• Political Persecution Claims by Trump