Trump Jr. tells court artist ‘make me look sexy,’ points to fake SBF sketch

As former president Donald Trump’s sons took the stand in the civil fraud trial against their family business, Donald Trump Jr. made a four-word request to the sketch artist capturing his image and likeness in the courtroom.

“Make me look sexy,” he said.

After Trump Jr. finished his Thursday testimony on the financial statements at the heart of the $250 million lawsuit, he approached courtroom sketch artist Jane Rosenberg and asked whether she could draw him in an overly flattering way. Rosenberg was on assignment for Reuters, the first to report on the exchange.

Trump Jr. had an example of what he should look like — and it came from another Manhattan courtroom. Rosenberg said he pulled out his phone and showed her the fake courtroom sketch of Sam Bankman-Fried, the FTX co-founder who was faces decades in prison after he was convicted of fraud, conspiracy and money laundering on Thursday.

“He said, ‘Did you see the one they made of Sam Bankman-Fried? It made him look like a superstar,’ ” she recounted to Insider. Rosenberg told Reuters she quickly shot down the AI-generated sketch of Bankman-Fried — depicting him as having spiky hair and a firm jaw instead of his usual disheveled self — as being fake.

“It doesn’t look anything like him, doesn’t look anything like Sam Bankman-Fried,” she said, “ … and there’s no one in the courtroom drawing that.”

Rosenberg, a veteran courtroom artist who has drawn sketches of everyone from Tom Brady to Harvey Weinstein, depicted Bankman-Fried throughout his trial as having big ears, a protruding forehead and bulging eyes.

Rosenberg did not immediately respond to a request for comment early Friday. Trump Jr. confirmed on X that he asked the artist to make him look good in his courtroom sketch.

“True story,” he wrote, sharing a side-by-side comparison of the fake courtroom sketch and a real photo of Bankman-Fried. “Seems like a reasonable ask.”

Trump Jr.’s sketch request comes as attorneys for New York Attorney General Letitia James (D) have accused the former president, his sons and their eponymous company of inflating the financial statements to secure better terms. The trial is examining the alleged long-standing practice by the Trump Organization and its executives that was done to negotiate better interest rates from lenders and to cut down on insurance policy costs.

As he was questioned by Colleen Faherty, a member of James’s trial team, Trump Jr. testified that he was not involved in the accounting that went into the financial statements, describing that as the work of the company’s accountants.

The former president’s namesake mentioned to Rosenberg how he wanted a flattering sketch like Bankman-Fried’s hours before the FTX co-founder was convicted. The jury’s decision was reached after less than five hours of deliberation, with Bankman-Fried being found guilty on two counts of wire fraud, four counts of conspiracy to commit fraud and one count of conspiracy to commit money laundering. The attorney for Bankman-Fried, who is accused of being one of the largest financial fraudsters in history after victims suffered nearly $10 billion in losses, suggested that his client will appeal the conviction. Bankman-Fried’s sentencing is scheduled for March 28, 2024.

Rosenberg is among the most well-known courtroom sketch artists in America. In the decades after she got her start drawing prostitutes in New York’s night court, Rosenberg has captured the likes of John Gotti, Woody Allen and Martha Stewart while they were on trial. Rosenberg faced some criticism a few years ago for her depiction of “ugly Tom Brady” during a Deflategate hearing in 2015. Her rendering of the New England Patriots quarterback made Brady, known for his handsome features, look as if he had gone through a gruesome transformation. The sketch caused a firestorm of internet memes and a deluge of nasty emails from Patriots fans.

Rosenberg is also no stranger to sketching a member of the Trump family in court. When the former president was arraigned in April on 34 counts stemming from 2016 hush money payments, Rosenberg drew sketches showing Trump’s anger after the first criminal charges were handed down to any former U.S. president. The sketch went viral and graced the cover of the New Yorker.

In the days before Bankman-Fried’s conviction, a fake courtroom sketch of him spread online that depicted him to be an Adonis, or at least an underwear model. The internet had fun over the AI-generated rendering.

“Why does courtroom sketch SBF look like he spends his time playing quarterback & breaking hearts when he’s not stealing customer funds?” one critic asked on X this week.

But the fake sketch of Bankman-Fried rankled Rosenberg, who maintained to the Independent that the AI-generated image “doesn’t look anything like him.” Rosenberg acknowledged to the British outlet that the courtroom sketch artists said the AI image looked more like Matthew Perry, the “Friends” star who recently died, than Bankman-Fried.

“It’s not Bankman-Fried, it’s not his nose, it’s not his face, it’s not anything,” she said. “You know that AI doesn’t work in courtroom art.” She added, “It’s so silly, this whole world of Twitter. So we’re talking about nothing.”

Rosenberg’s courtroom depictions of Bankman-Fried changed during the course of the month-long trial, with some comparing his droopy and unsettling features to that of “The Scream,” the 1893 composition by Edvard Munch that symbolizes the anxiety of the human condition.

Like any of her other sketches, including Trump Jr., Rosenberg told the Independent that her process for drawing the real sketch of Bankman-Fried was simple, and that it wasn’t her job to analyze whether defendants were tragic figures.

“I just look at him and draw what I see,” she said.

Shayna Jacobs, Mark Berman, Eli Tan and Tory Newmyer contributed to this report.