Donald J. Trump’s family business lost a criminal contempt trial that was held in secret last fall, according to a newly unsealed court document and several people with knowledge of the matter, with a judge ruling against the company almost exactly a year before it was convicted of a tax fraud scheme last week.
The document, a judicial order released Tuesday, showed that in October 2021, a one-day contempt trial was held after prosecutors with the Manhattan district attorney’s office requested that the company be punished for “willfully disobeying” four grand jury subpoenas and three court orders enforcing compliance.
The order, dated Dec. 8, 2021, was unsealed by the judge who presided over the tax fraud trial of the Trump Organization, which ended last week with the conviction of the company. It redacted the name of the entities on trial in October, but the people with knowledge of the case confirmed that those entities were the Trump Organization corporations that later went on trial for tax fraud. The judge, Juan Merchan, convicted the two corporations of criminal contempt of court and fined them $4,000, the maximum under the law.
“The record is clear that the company failed to produce responsive documents without explanation,” Justice Merchan wrote in his order.
The fine amounts to less than a slap on the wrist, but the contempt order underscores the pitfalls of Mr. Trump’s go-to legal strategy of delaying proceedings and fighting subpoenas whenever possible. It was the second time in less than a year that Mr. Trump or his company was held in contempt for failing to turn over documents, the other instance coming in the New York attorney general’s civil inquiry into the former president’s business practices.
A spokeswoman for the Manhattan district attorney, Alvin L. Bragg, declined to comment Tuesday. A spokeswoman for the Trump Organization did not immediately respond to a request for comment.
After securing the conviction of Mr. Trump’s company last week, Mr. Bragg’s office has continued its long-running inquiry into the former president himself. The investigation has a dual focus: a hush-money payment to a porn star who said she had an affair with Mr. Trump, and the potential overvaluation of assets on the former president’s annual financial statements.
In 2020 and 2021, Mr. Trump, his company and his lawyers were flooded with subpoenas, relating to both the district attorney’s criminal inquiry and a civil investigation into Mr. Trump’s financial statements by the New York attorney general, Letitia James. According to the order released Tuesday, a company representative testified in January 2021 to having “successfully responded to countless subpoenas” in the past. But that March, prosecutors told the court that a number of the requested documents had not been turned over.
The October contempt trial was kept secret because it was related to subpoenas issued by a grand jury, the work of which is sealed. The grand jury remained active after the Trump Organization and its chief financial officer, Allen H. Weisselberg, were charged with crimes in July 2021.
More than a year later, Mr. Weisselberg pleaded guilty to the tax fraud scheme, in which he and other executives were compensated with off-the-books perks. The company declined to plead guilty, and the case went to trial in October. Last week, the company — specifically two of its corporations, the Trump Corporation and the Trump Payroll Corp. — was convicted of 17 felonies.
Mr. Trump was also held in contempt of court in April amid Ms. James’s civil investigation. Lawyers from her office had accused him of not fully complying with a subpoena, and a judge, Arthur F. Engoron, imposed a $110,000 penalty. In September, Ms. James sued Mr. Trump, three of his children and his company, accusing them of overvaluing their assets by billions of dollars.
Contempt of court is hardly the only threat Mr. Trump faces for declining to turn over documents in a timely manner. Federal prosecutors, along with investigating the former president’s removal of sensitive documents from the White House, are seeking to determine whether he obstructed efforts to retrieve those materials.
Last week, a federal judge declined to act on a request from federal prosecutors to find personnel in Mr. Trump’s post-presidential office in contempt of court, also for failure to comply with a subpoena.