Donald J. Trump Jr. was back in Manhattan Supreme Court on Monday as the defense’s first witness in the civil fraud trial that could upend his family’s real estate empire.       

“Welcome back,” teased the presiding judge, Arthur Engoron. The eldest of President Trump’s sons had already taken the stand on November 1 and 2, having been subpoenaed by the prosecution. 

“You thought you were rid of me, your honor,” Mr. Trump bantered back.  Later he added, “I’d say it’s good to be here, your honor, but I think the attorney general would sue me for perjury.” 

New York’s attorney general, Letitia James, is suing Donald Jr., his younger brother Eric, their father Donald J. Trump and other associates of the Trump Organization for business fraud. In her complaint, Ms. James alleges that the Trumps falsely inflated and deflated asset values in a decades-long scheme to secure favorable loans and insurance policies. 

Ms. James is demanding that an “independent monitor” take over the Trump Organization “for a period of no less than five years,” and that the defendants be “permanently barred” from “serving as an officer or director” in any business “registered and/or licensed in New York State.”

The legal proceedings have already gone poorly for the Trumps. In a pre-trial ruling, called a summary judgment, which is granted when the facts can be decided without needing to go to trial, Judge Engoron already partially decided the case.

He found the defendants guilty of committing fraud and granted the attorney general’s request to revoke their New York business licenses. Yet an appellate court halted the revocations, pending the outcome of the defense’s appeal. In simpler words, the Trumps continue to hold their licenses and control their famed properties until the appeals court decides otherwise. 

Meanwhile, the hearing currently underway in Judge Engoron’s courtroom is to determine the damages. There are still six open legal claims that the attorney general’s lawsuit alleges against the Trump Organization. These include submitting false financial records, insurance fraud and conspiracy. Judge Engoron must now decide who, if anyone, is liable for these claims, and whether to fine anyone and, if so, how much. Ms. James is asking for an estimated $250 million fine, plus interest.

On Monday, Donald Jr. didn’t appear to be too worried. He leaned back in his seat and smiled as he answered questions from one of his attorneys, Clifford Robert. Sounding much like his father, Mr. Trump described the “iconic”, “amazing” and “extraordinary” Trump properties in lengthy detail. 

By sharing a slideshow titled “The Trump Story,” the defense intended to legitimize the legacy of the Trump family, which dates back to the end of the 19th century, when German born Frederick Trump, Donald Jr.’s great-grandfather, made a fortune with restaurants for miners during the Klondike Gold Rush in Canada’s Yukon territory.

“It is relevant to get the historical perspective,” Judge Engoron commented as he allowed the testimony to unfold with few interruptions over the next three hours. He only criticized Donald Jr. for speaking too quickly. “We like the enthusiasm but try to limit the speed,” he told the witness.  

In his previous testimony, Donald Jr. had stated that he began working for his father’s organization shortly after 9/11, when he was about 25, doing “anything and everything,”  from project manager to licensing deals, international business matters, leasing and branding.  

“I don’t recall my specific titles,” he had told an Assistant Attorney General, Colleen Faherty, two weeks ago, when she pressed him to specify his roles at the Trump Organization. Now the defense gave him the chance to elaborate further, again asking about the importance of titles at the company. 

Donald Jr. clarified that it’s “much more of a meritocracy,” that his family company is run in “a mom and pop” fashion, led by his father’s guiding principles and vision. 

“He’s an artist with real estate. He sees the things other people don’t,” Donald Jr. boasted. “He has incredible vision that other people don’t.” 

For example, his father had the vision to offer gyms as amenities in luxury buildings. Though Donald Jr. later admitted that the Trump Organization may have not been the first company to add gyms, he emphasized that no one had built them as big and grandly as his father had. He further described his father’s ability to spot a “diamond in the rough” and turn run-down properties into “sexy” and “spectacular” real estate assets. 

The defense sought to substantiate its claim that Trump’s properties were in fact “extraordinary” and “iconic” by presenting a series of photographs of golf courses in Scotland, Ireland, and even in the Bronx, bathed in the warm glow of afternoon sunlight. 

Judge Engoron appeared to be more lenient with the defense than he had been on previous days. He allowed the defense to submit a third party’s valuation of Trump’s National Doral Miami resort into evidence. The February 2022 valuation estimated the property to be worth $1.3 billion. 

The attorney general’s office objected, arguing that the document was dated outside the relevant time period. The judge overruled the objection and told the defense that he was giving them “the benefit of the doubt.” But, he added, “I can’t see any relevance.”

As the prosecution attempted to engage further in the argument, the judge told the lawyers, “Do you want to risk a reversal over this one stupid document?”

During Ms. Faherty’s brief cross examination, Donald Jr. was questioned about a drop in the occupancy rate in their property on 40 Wall Street, in downtown Manhattan.  

In his direct examination he had told the court that the occupancy rate was around 90 percent. But Ms. Faherty indicated that according to a recent statistic the rate had dropped to 77 percent. 

“The last time I checked it was in the 90s,” Donald Jr. said, brushing off the attack on his credibility. He also denied any knowledge that the loan for 40 Wall Street had recently been put on a servicer’s watch list. 

Then Ms. Faherty inquired about Trump International Hotel Waikiki in Hawaii that is currently buying itself out of the Trump brand to become a Hilton.  

“It’s buying itself out of a management agreement, yes,” agreed Donald Jr., adding that this was not uncommon, and that the hotel would have to pay millions of dollars to do so.    

With that, Donald Jr. was excused, and the defense called their next witness, Sheri Dillon, a tax attorney. 

Ms. Dillon’s law firm did work for the Trump Organization and she advised Donald J. Trump, after he became president, about separating his personal affairs from his business in order to avoid conflicts of interest. Her testimony began to explore benefits of conservation easements as the court day ended. The defense will continue questioning Ms. Dillon on Tuesday morning.  

The trial is moving forward after defense attorney Chris Kise filed a motion last week for a “directed verdict” in an attempt to end the case immediately. 

“There is no victim. There is no complainant. There is no injury,” Kise said on Thursday.

The judge has not commented on the motion yet, but will most likely deny it, just as he did previously when another defense attorney asked him to dismiss the case after former President Trump’s sometime fixer, Michael Cohen, had testified.  

Outside the courtroom, Donald Jr. told reporters that it had been “a little bit of a rough day.” He seemed annoyed that he still had to, as he said, “deal with this stuff.” 

“You gotta keep doing it, that’s the nature of all this stuff,” he added. As the cameras flashed, he shrugged. “At this stage in our lives, it’s just another day,” he said. Whether his younger brother Eric will be called back to testify for the defense is uncertain.

It is believed that their sister Ivanka, who unsuccessfully resisted being called by the prosecution, will not return to court. The defense has signaled that they intend to bring Donald Trump himself back to the courtroom, though it is not yet clear when he will take the stand.