The request allegedly came during a rest period in the case on Thursday. He had been testifying for several hours about his involvement in questionable financial statements made by the Trump Organization that a judge already deemed fraudulent.
Once his testimony was finished, the court took a break, and Mr Trump Jr rushed over to a sketch artist, Jane Rosenberg, who was there on assignment for Reuters.
Ms Rosenberg said that Mr Trump Jr specifically asked that she "make me look sexy" in her recollections of the day’s events. He suggested she look at a flattering illustration of disgraced cryptocurrency mogul Sam Bankman-Fried to inspire her as she sketched him. The former president's son said the sketch made the king of the crypto ruins look like a "superstar."
The sketch in question shows Mr Bankman-Fried as square jawed, with spiky hair and impeccable posture. In reality, Mr Bankman-Fried does not resemble the main character from a courtroom anime. That lack of any kind of resemblance was apparently just fine for Mr Trump Jr.
"I said, 'That's fake,'" Ms Rosenberg said. "It doesn't look anything like him, doesn't look anything like Sam Bankman-Fried ... and there's no one in the courtroom drawing that."
Of all of Donald Trump’s adult children, Don Jr has arguably done to most to elevate his public image. Ivanka, Mr Trump's daughter, has largely dropped out of public life, while Eric and Tiffany spend less time courting drama.
Mr Trump Jr, on the other hand, has leaned into the hard-right MAGA brand his father successfully sold to US conservatives. Despite growing up in the lap of luxury, he frequently plays himself up as an everyman. He has previously posted photos posing with animal corpses while wearing camo and holding rifles.
His focus on his court appearance wasn't limited to the Reuters sketch artist; he joked that he "should have worn makeup" after a gaggle of photographers rushed to take his photo on his first day in court.
Mr Trump Jr ultimate told the court that he had no dealings with the financial statements at the centre of the fraud case, arguing that he had no involvement in any of the alleged misrepresentation of assets that triggered the investigation.