The eldest son of the former president appeared confident on the stand as he testified on Wednesday.
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“I should have worn make-up,” Donald Trump Jr quipped on Wednesday as a group of photographers rushed into court to take his picture.
As an executive at the Trump Organization, he was testifying in a multimillion-dollar civil trial that could see his family lose a sizable part of its business empire.
His comment set the tone for what was an hour-long charm offensive that saw Mr Trump Jr lightheartedly engaging with the judge while letting his lawyers do the brawling for him.
The eldest son of the former president appeared confident and relaxed on the witness stand. He smiled during proceedings, even making the occasional joke and drawing laughter from the courtroom.
The stakes, however, were high and the claims against him serious.
The judge has already found the Trump Organization falsified business records. This hearing will resolve other claims and potential penalties, which, in a worst-case scenario for the family, could see Mr Trump Jr, along with his father and brother Eric, essentially lose the ability to do business in New York
But Mr Trump Jr did not appear perturbed. Wearing a dark blue suit and flamingo-pink tie, the current Florida resident quipped to the judge that he had “kept the New York pace” after being asked to speak more slowly.
At another point, Judge Arthur Engoron noted humorously that Mr Trump Jr could settle a minor pronunciation argument: whether to pronounce “revocable” as “re-VOCK-able” or “re-VOKE-able”.
Mr Trump Jr laughed and said he did not know.
When Colleen Faherty of the attorney general’s office then phrased her question with one pronunciation, Mr Trump Jr joked that he only understood the other.
On another occasion, Ms Faherty pressed the 45-year-old on his understanding of the guidelines businesses use to ensure financial records are accurately maintained. He drew chuckles as he smiled and responded: “I have no understanding” – part of his broader argument that he was not involved in the minutiae of the company’s accounting as prosecutors have claimed.
The attorney general’s office argues he and his brother Eric were “intimately involved” in the Trump Organization, and said in court filings that they were “aware of the true financial performance of the company”.
Mr Trump Jr’s jovial persona on Wednesday was notably different to the hyper-masculine right-wing influencer he usually portrays.
In an appearance on the conservative Newsmax network earlier this week, he called the trial a “sham” and and labelled the chamber a “kangaroo court”.
But he refrained from airing such bombastic criticism in court. While Judge Engoron appeared in decent spirits, he had earlier fined Mr Trump Jr’s father $15,000 (£12,300) for levelling political attacks against court staff.
Most of Ms Faherty’s questioning focused on establishing Mr Trump Jr’s work at the Trump Organization and his involvement in the preparation of various financial documents that had come under the attorney general’s scrutiny.
Anticipation for this phase of the trial had been building since it began on 2 October. Mr Trump Jr is the first of his siblings to give testimony, with Ivanka and Eric Trump scheduled to do so in the coming days. Donald Trump himself may take the stand next week.
And while Mr Trump Jr faced a relatively drama-free day on Wednesday, the tone could change as the attorney general’s team resume their questioning on Thursday morning.