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What to watch when Donald Trump takes the stand in New York civil fraud trial

By Jeremy Herb, CNN

(CNN) — Former President Donald Trump will take the stand Monday to give high-stakes testimony that could help decide the fate of his business empire in New York.

Trump is testifying in the civil fraud trial brought by New York Attorney General Letitia James, who is seeking $250 million in damages and to bar the former president from doing business in the state. James alleges that Trump and his co-defendants committed repeated fraud in inflating assets on financial statements to get better terms on commercial real estate loans and insurance policies.

While there are no criminal charges involved, the allegations have enraged the former president, who has attended the trial for multiple days and attacked it as a political witch hunt.

Judge Arthur Engoron already ruled before the trial began last month that Trump and his co-defendants, including his adult sons, were liable for “persistent and repeated” fraud. Now the judge is considering how much the Trumps will have to pay in damages for the profits they’ve allegedly garnered through fraudulent business practices.

The attorney general’s office is also looking to prove six other claims: falsifying business records, conspiracy to falsify business records, issuing false financial statements, conspiracy to falsify financial statements, insurance fraud and conspiracy to commit insurance fraud.

Trump’s testimony Monday will be the first chance to see how he responds in the face of hostile questioning, a precursor to the four criminal trials he faces next year as he campaigns to regain the presidency.

The trial is not televised, but Trump’s appearance on the witness stand will mark arguably the highest-profile moment of his 2024 presidential campaign – a campaign in which Trump has repeatedly cited his own legal peril as a key reason voters should return him to the White House.

Here’s what to watch on Monday – and what’s at stake for Trump:

Trump on the stand

Trump has relentlessly attacked James for bringing the case against him. He’s attacked the judge for being biased against him. He’s attacked the judge’s law clerk for being biased, too.

Trump’s conduct at the trial has already been a flashpoint – he’s been fined twice for violating a gag order barring him from speaking about the judge’s staff.

Those attacks will be the backdrop when the former president is sworn in to testify Monday morning. He’ll be required to answer the attorney general’s team’s questions, which are expected to dive into the minutiae of Trump’s personal financial statements and valuations of his real estate properties.

How Trump responds to the interrogation will be scrutinized closely. During testimony from the president’s adult sons, Donald Trump Jr. and Eric Trump, the attorney general’s lawyers admonished the witnesses for making speeches instead of answering “yes” or “no” questions. Trump, of course, is not known for being short with his rhetoric.

Trump is also known for spreading falsehoods, both big and small, which could get him into trouble while he’s testifying under oath.

While Trump the defendant will be somewhat restricted in his responses inside the courtroom, Trump the candidate won’t be when he speaks to the cameras right outside.

When he has attended the trial, Trump has made a point of speaking whenever he enters or leaves the courtroom, frequently railing against the trial.

That’s also gotten Trump in trouble. When he was attending his former lawyer Michael Cohen’s testimony, Trump spoke to cameras outside the courtroom and accused the “person sitting alongside” the judge of being biased – an apparent violation of Engoron’s gag order.

Engoron dragged Trump to the witness stand to testify, in an impromptu hearing about the violation. Trump claimed he was talking about Cohen, not the clerk. Engoron responded his testimony was “not credible,” fining him $10,000 for the gag order violation.

Why this case matters to Trump

The civil case is important to Trump because it strikes at the heart of his persona as a billionaire real estate tycoon: The New York attorney general is accusing the former president of inflating his net worth to save hundreds of millions of dollars.

The case also has real consequences for the Trump Organization: James is seeking to bar Trump from doing business in the state and to dissolve his companies.

The attorney general has accused Trump, his two adult sons, the Trump Organization and several company executives of inflating Trump’s net worth by as much as $3.6 billion to obtain better terms on commercial real estate loans and insurance policies. An expert witness for the attorney general testifying last week alleged the ill-gotten gains totaled $168 million.

Trump’s lawyers have disputed the allegations, arguing that asset valuations are highly subjective. They’ve also attacked the proceedings in Engoron’s courtroom as biased against the former president, signaling a plan to appeal.

Eric Trump and Donald Trump Jr. testified last week, distancing themselves from the preparation of the president’s annual “statements of financial condition” in which the values of Trump’s properties are alleged to have been inflated.

Cohen testified that Trump directed him and Allen Weisselberg, the Trump Organization’s former chief financial officer, to inflate the property values, though he then contradicted himself and said that Trump had not specifically told him to do so, but it was implied what he should do. Weisselberg testified that the meeting never happened.

While Trump has claimed that Cohen’s contradictions clear him, Engoron “absolutely denied” a motion from Trump’s attorneys to dismiss the case, saying there was still a pile of evidence beyond Cohen.

Trump will be pressed on his properties

Much of the questioning of Trump will involve the properties that are the backbone of his business, including the 40 Wall Street building in New York, Trump National Doral Miami golf course and resort, Trump International Hotel & Tower in Chicago, and the Old Post Office project in Washington, DC. The attorney general has also alleged Trump inflated the value of his triplex apartment in Trump Tower.

And perhaps most importantly: The tax status and value of Trump’s Mar-a-Lago resort in Florida are at issue in the case.

Trump has repeatedly pointed to a line in the judge’s September ruling that Mar-a-Lago was worth $18 million to argue the decision was fatally flawed.

In court, Trump’s attorney Alina Habba claimed that Mar-a-Lago would sell for at least $1 billion. “The value is what someone is willing to pay. The Trump properties are Mona Lisa properties,” Habba said.

The $18 million valuation, based on a tax assessor’s appraisal, has been questioned by real estate insiders. Engoron said in court he was not valuing the property in his decision.

But the Mar-a-Lago valuation is just one of the instances in which Trump is likely to push back against claims that the values of his properties were inflated.

Testimony from the whole family

Trump’s testimony follows the appearance of his adult sons, Donald Trump Jr. and Eric Trump, last week. And his daughter Ivanka Trump is slated to take the stand Wednesday, after she dropped an appeal to the judge’s ruling requiring her testimony.

Ivanka Trump is not a co-defendant in the case, after an appellate court dismissed her as a defendant because she was outside the statute of limitations.

Trump’s attorneys did not cross-examine Donald Trump Jr. or Eric Trump. It’s not yet clear whether they plan to ask Donald Trump any questions after he is questioned by the attorney general’s team.

The expectation is that Trump’s testimony will take place only on Monday, though it’s always possible it could spill into Wednesday. (Court is closed Tuesday for Election Day.)

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