The Most Awkward Moments From Donald Trump's Trial

After commandeering one of the most divisive presidential terms in U.S. history, former Oval Office seat warmer Donald Trump finds himself glopping in a swamp of trouble with nary a drain in sight. Two impeachments already taint his presidential record and he currently faces 91 criminal charges, nearly half of them concerning his attempt to overthrow a federal election he lost in 2020. There's more. Trump stands to lose up to $250 million and the likelihood of never again being able to run a real state business in New York if Attorney General Letitia James has her way. In September 2022, James announced she'd take Trump to civil court after a three-year investigation revealed that his company frequently cooked the books by spiking the values of its holdings to attract investors and dropping them to cut down on paying taxes. The law calls it fraud, of which Trump's already been declared guilty, via a ruling by New York supreme court judge Arthur Engoron weeks before the trial started October 2.

Although Trump won't face jail time, he's predictably been defiant about the civil suit. Back in April, Trump reportedly told James in her office, "You don't have a case and you should drop this case," per CTV News. That retort has been small potatoes compared to the bluster he's since created. From threats and insults to outlandish claims, Trump has turned this trial into a sideshow that would have impressed P.T. Barnum. Here's how the score card reads so far.

The civil trial pitting Donald Trump against the state of New York has been five years in the making, ever since Letitia James became Attorney General in 2018. Since then, she's vowed to take down the real estate magnate whose business has endured litigation for decades. "He should know that we here in New York—and I, in particular–we are not scared of you," said James the night she became AG, per BBC. 

So far, the civil suit announced in 2022 was just the beginning. She also nailed Trump with a daily $10,000 fine for not providing her office with classified documents needed by the prosecution. Outraged, Trump fought back with a lawsuit of his own against James, calling her actions a politically-motivated "witch hunt," while accusing her of "intimidation and harassment," per ABC News. He eventually dropped the suit. More damaging comments surfaced mere days before the trial when Trump was a guest on WABC 770 AM's "Cats at Night" show. "She's a horror show," Trump said, per The Hill. "She doesn't care about violent crime. She doesn't care about anything except trying to use Trump's name to get elected. And she's a disaster and everybody knows it."

He's also had it in for Supreme Court Justice Arthur Engoron, whom he attacked on Truth Social. "I have a Deranged, Trump Hating Judge, who RAILROADED this FAKE CASE through a NYS Court at a speed never before seen," posted Trump, per Politico.

The first day of the trial saw Donald Trump scowling throughout the proceedings, his face turning beet-red when the prosecution argued that his company had overvalued its holdings by as much as $2.2 billion . He relaxed somewhat when the defense opening remarks suggested that changes in valuation were pretty routine when it came to property being assessed or changing hands. "That is not fraud, that is real estate," said Alina Habba, one of Trump's lawyers, per Guardian. "I had the pleasure of visiting these properties, and they are not humble properties." Habba later added that Attorney General Letitia James, a Democrat, took their Republican client to court on political grounds, especially given his success in real estate. "There are probably a lot of people in this room that don't like that and that's why we're here," she noted.

For the most part, Trump behaved himself in court. Outside, it was a different matter. Before he stormed into court, Trump remarked to media outside that the whole case was a sham. "This has to do with election interference, plain and simple," Trump said, per CNN. "They're trying to damage me, so I don't do as well as I'm doing in the election." During lunch break, Trump was once again in fine form, venting his rage at judge Arthur Engoron. "This is a judge that should be disbarred," he declared, per NBC News. "This is a judge that should be out of office." 

Of the 23 witnesses that Attorney General Letitia James' legal team had on their list to bolster their case, they hoped that former Trump Organization CFO Allen Weisselberg–who was found guilty of tax fraud in a separate case and spent three months in jail–would be a smoking gun. The prosecution anticipated Weisselberg's participation in the inner workings of Trump's organization would provide valuable fodder to their arguments. 

What they got instead was a testimony that did nothing to add to Weisselberg's credibility, creating suspicion that the witness was still loyal to Trump. One contentious issue concerned his former boss's luxury New York penthouse atop Trump Tower, which occupied some 10,000 square feet. Weisselberg estimated that it was three times that size, and at one point had valued it as high as $200 million, although a reporter initially pegged the apartment's worth at $64 million in 2012. When questioned about the physical discrepancy, Weisselberg responded, "I never focused on the apartment Mr. Trump owned," he said, per Forbes, adding later, "I didn't correlate the square footage of Donald's apartment. I never focused on it." But Forbes contended that several emails and memos involving Weisselberg revealed the former CFO had more intimate knowledge of the penthouse than he let on.

Armed with a stockpile of insults that would have rivaled Don Rickles, Donald Trump has been notorious for delivering cheap shots by the truckload, most of them at women. So it wasn't a surprise that early in the civil trial, he fired a scornful missive at law clerk Allison Greenfield on his Truth Social account. After finding an Instagram shot of Greenfield on Instagram posing with Democrat and Senator Majority Leader Chuck Schumer, Trump declared the two were having a romantic relationship, which was enough to jeopardize his trial. "Schumer's girlfriend, Alison [sic] R. Greenfield, is running this case against me. How disgraceful! This case should be dismissed immediately," Trump wrote, per Raw Story.

Judge Arthur Engoron went ballistic. "Personal attacks on members of my court staff are unacceptable, inappropriate and I will not tolerate them in any circumstances," declared the judge, per Politico, before imposing a gag order on Trump, ordering him to remove the post. It quickly disappeared from Truth Social, but remained on his campaign page for more than two weeks, prompting Engoron to fine Trump $5,000 for refusing to obey a gag order. Later in October, Trump alluded to Engoron and the law clerk in the courtroom hallway within earshot of reporters. "This judge is a very partisan judge with a person who is very partisan sitting alongside him – perhaps even much more partisan than he is," Trump said, per CNN. He was fined an additional $10,000.

Donald Trump wasn't the only person who took issue with law clerk Allison Greenfield. His lawyers also objected to her actions that included passing notes and whispering to Judge Arthur Engoron. Tying those in with Greenfield's Democrat ties, one of Trump's lawyers, Christopher Kise, hinted that he might declare a mistrial. "We all need to take this very seriously because the entire world is watching," he declared, per Guardian. Audiences are doing more than just watching, alluded Engoron. Some were even flooding the judge's chambers with messages of harassment and threats.

At one point, Engoron suggested Kise's accusation was misogynist, an allegation the lawyer denied on account that he was happily married with a 17-year-old daughter. But Kise's colleague, Alina Habba, added she also objected to Greenfield's actions. "I have the same, frankly, issues with the person sitting on the bench, and I've made that clear on the record," she said, per ABC News.  Prosecutors also chimed in, claiming that the ruckus raised by Trump's team was a distraction to throw the trial off-track. Tired of the bickering, Engoron declared, per HuffPost, "I have an absolute, unfettered right to get advice from my principal law clerk." He also extended the gag order on Trump to include his lawyers.

One witness that Attorney General Letitia James' legal team was counting on for damning evidence was from lawyer Michael Cohen, who previously worked for Donald Trump until five counts of tax evasion sent him to jail in 2018. And amid the tension mounting in the courtroom, Cohen did not disappoint. Later remarking that he had a "heck of a reunion" with his ex-employer with Trump seated a few feet from the witness stand, Cohen described how he worked in conjunction with former Trump CFO Allen Weisselberg to fudge numbers on assets to prop up their net worth. "The topic was the statement of financial condition," Cohen recalled, per CNN. "He would look at the total assets and he would say 'I'm actually not worth 4.5 billion, I'm really worth more like six.' He would then direct Allen and I to go back to Allen's office and return after we achieved the desired goal."

Trump was probably tempted to grab Cohen by the throat. Instead, that job was taken by one of his lawyers, Alina Habba. Indicating that Cohen had eventually became a turncoat against his boss, while calling him a perjurer and serial liar," Habba boldly asked, "You have made a career of publicly attacking President Trump, haven't you?" "Yes," answered back Cohen, per Guardian. After the trial had adjourned for the day, Trump said that Cohen was a "disgraceful fellow" to reporters. "The witness is totally discredited already," he added, per Reuters.

Named with his father and brother as a co-defendant in the civil trial Donald Trump Jr. can be just as vocal and derisive as the former U.S. president. But he managed to retain his composure during what seemed like a marathon session on the witness stand. Before the gavel banged to begin the day's proceedings, he quipped in front of a cluster of media photographers, "I should have worn makeup." Once his testimony had concluded, he told courtroom sketch artist Jane Rosenberg, per Reuters, "Make me look sexy," a reference to what he believed was a previous Rosenberg work of Sam Bankman-Fried, another celebrity on trial for fraud. That image, according to Trump Jr., made the defendant look like a "superstar." Rosenberg, however, said that AI deserved the credit for that caricature.

The biggest takeaway from his testimony, however, wasn't anywhere near as colorful as those visage references, as Trump Jr. denied he administered any elbow grease on the financial documents covered in court. But as an executive vice president and trustee of father Donald Trump's interests in the organization that bears his name, he admitted signing off on those papers. "I wasn't working on the document, but if they tell me that it's accurate, based on their accounting assessment of all of the materials," said Trump Jr., per Fortune, who became trustee when his father became president. "These people had an incredible intimate knowledge, and I relied on them."

Like Don Jr., Eric Trump is an executive vice president of his father's company, is listed as a co-defendant, and also denied working on contentious financial statements. While his older brother seemed as cool as a cucumber during testimony, Eric apparently didn't retain the same demeanor. When the prosecution displayed an email countering Eric's denial, he replied he regularly communicated with company executive Jeff McConney, another trial co-defendant. But he seemed to have trouble understanding why some of those documents particularly interested the Attorney General. "What seems to not be registering is the difference between sending things used for financials and sending things used for a statement of financial condition," he admitted, per CNN.

That response might spell snoresville to armchair jurists, but it's a big deal to bean counters and lawyers. Things used for financials are necessary for reports demonstrating company performance. Things used for a statement of financial condition, however, provide evidence of fraud, in this case, his father's personal financial documents. The prosecution pointed those "things" could be found in transactions involving Trump holdings like the Doral Golf Resort and Seven Springs, as well as a Briarcliff Manor project roughly valued at $58 million lower than what the former president's statements indicated. It turns out that Eric had some explaining to do, as the tension barometer in the courtroom continued to rise. It turns out he was busy. "I'm on a thousand calls a day," Eric said, per AP.

Judge Arthur Engoron might have been in charge of running the courtroom, but the ringmaster of the legal circus was still Donald Trump. He frequently traded barbs with the judge, who slapped a gag order on the former president and fined him twice when the defendant violated it. During his own testimony, Trump was in fine form. He seldom answered questions, rather preferring to use his time on the stand to unleash a truckload of vitriol at the judge and prosecution. "It's a terrible thing you've done," Trump angrily bellowed, per Politico. "You know nothing about me." Then he went after Attorney General Letitia James, responsible for taking the Trump contingent to court in the first place. "You believe that political hack back there."

For his part, Engoron did what he could to prevent Trump from using the witness stand as a personal soap box, even threatening to remove him. "This is not a political rally," Engoron said at one point to the star defendant, per CNN. At one point, he told Christopher Kise, one of Trump's lawyers, to "control your client." Engoron said to Trump, telling Trump's attorney Christopher Kise to "control your client." What answers the prosecution got out of Trump were vague and cavalier at best, especially when it came to statements that allegedly distorted the value of his assets. "They were not really documents that the banks paid much attention to," he said at one point, per ABC News.

Ivanka Trump was initially named in the civil trial affecting her father and brothers, until a statute of limitations appeal put her in the clear. Still, the Attorney General's legal team wanted her on the stand as their final witness anyway, a situation she doggedly tried to avoid . Ivanka's testimony was hardly dramatic, but it raised a few questions about her culpability. 

One query concerned a 2011 Deutsche Bank loan to finance development of a golf course in Florida. Memos indicated that Donald Trump needed to be worth $3 billion to qualify, although subsequent drafts indicated Ivanka managed to lower that requirement to $2.5 billion. At the time, Trump's financial statements pegged him a being worth $4.2 billion. "We wanted to get a great rate and the only way to get proceeds/term and principal where we want them is to guarantee the deal," said Ivanka in another memo to a company lawyer, per Reuters. When the prosecution brought up the inconsistencies regarding her father's net worth, and that Ivanka might have personally benefited from some transactions, she drew a blank. "There were many emails, many conversations," she said.

While Attorney General Letitia James was impressed with Ivanka's demeanor on the stand, she was still suspicious over what was said or even left unsaid. "Ivanka Trump was cordial," noted James, per CNBC. "She was disciplined. She was controlled. And she was very courteous, but her testimony raises some questions with regards to its credibility."