“I should wear makeup,” Donald Trump Jr. joked Wednesday as a group of photographers rushed to the courthouse to snap his picture.

As an executive at the Trump Organization, he testified in a multimillion-dollar civil trial that could see his family lose a significant portion of their business empire.

His comment set the tone for an hour-long charm offensive in which Mr. Trump Jr. engaged nonchalantly with the judge while letting his lawyers do the fighting for him.

The eldest son of the former president acted confidently and relaxed on the witness stand. He smiled throughout the proceedings, occasionally even cracking a joke, drawing laughter from the courtroom.

A judge has already found that the Trump Organization falsified business records. That hearing will resolve other claims and potential penalties that, in the worst-case scenario for the family, could result in Mr. Trump Jr., along with his father and brother Eric, essentially losing their ability to do business in New York.

But Mr. Trump Jr. didn’t seem fazed. Dressed in a navy blue suit and flamingo pink tie, the current Florida resident joked to the judge that he was “keeping a New York pace” after being asked to speak more slowly.

On another point, Judge Arthur Engoron wryly noted that Mr. Trump Jr. could settle a minor pronunciation dispute: whether to pronounce “revocable” as “re-VOCK-able” or “re-VOKE-able.”

Mr. Trump Jr. laughed and said he didn’t 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 second.

On another occasion, Ms Faherty asked the 45-year-old to understand the guidelines companies use to ensure accurate financial records are kept. When he smiled, he laughed and replied, “I don’t understand” — part of his broader claim that he was not involved in the details of the company’s accounting, as prosecutors claimed.

The attorney general’s office claims he and his brother Eric were “closely involved” in the Trump Organization and said in court documents that they were “informed of the company’s true financial performance.”

Mr. Trump Jr.’s jovial persona on Wednesday was a stark contrast to the hypermasculine right-wing influencer he usually portrays.

In an appearance on the conservative Newsmax network earlier this week, he called the trial a “sham” and called the Senate a “kangaroo court.”

But he refrained from 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 political attacks on court staff.

Much 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 were under the attorney general’s scrutiny.

This phase of the trial has been anticipated since it began on October 2. Mr Trump Jr is the first of his siblings to testify, with Ivanka and Eric Trump expected to do so in the coming days. Next week, Donald Trump himself may make an appearance.

And while Mr. Trump Jr. faced a drama-free day on Wednesday, the tone could change when the attorney general’s team resumes questioning on Thursday morning.