N.Y. Prosecutors Weigh Charges Against Another Trump Executive

At least one employee at Donald J. Trump’s family business testified before a grand jury on Thursday as prosecutors in Manhattan examined whether to prosecute a senior officer at the organization with tax-related offenses, according to people with knowledge of the case.

The Manhattan district attorney’s office is scrutinizing whether the executive, Matthew Calamari, benefited from what prosecutors have described as a 15-year scheme at the Trump Organization to help its top leadership evade taxes by compensating them with off-the-books luxury perks such as free cars and apartments.

The move came two months after the district attorney’s office indicted the Trump Organization’s top financial officer, Allen H. Weisselberg, and the firm itself over the benefits.

Matthew Calamari, the chief operating officer for the Trump Organization.

It is uncertain if the authorities will pursue Mr. Calamari, who previously worked as Mr. Trump’s bodyguard and progressed over four decades to become the Trump Organization’s chief operational officer.

Mr. Calamari’s son, Matthew Calamari Jr., who is the 28-year-old corporate director of security at the Trump Organization, testified before the grand jury on Thursday.

Jeffrey McConney, who has long served as the Trump Organization’s controller and handled the elder Mr. Calamari’s taxes, had also been set to speak.

Two people close to the case, who spoke on the condition of anonymity because they were not authorized to discuss the inquiry, believe that the prosecutors will decide in roughly the next month whether to charge the elder Mr. Calamari.

If they do not charge him, they could demand his testimony before the grand jury as part of a wider probe into the financial practices of Mr. Trump and his firm. Prosecutors, who twice petitioned to the United States Supreme Court to acquire access to Mr. Trump’s tax returns, are exploring whether Mr. Trump or the corporation committed tax, insurance or bank-related fraud.

Under state law, witnesses who testify before the grand jury enjoy immunity from prosecution on the subject of their testimony, which means they cannot invoke their Fifth Amendment right to decline to answer questions. If they lie, though, they still can be charged for perjury.

“Matt Calamari Jr. was subpoenaed to testify before the grand jury,” said Nicholas A. Gravante Jr., a lawyer representing both the father and son. “He appeared today, was vaccinated and testified truthfully, all of which are required by law. He is a model citizen, has never committed any law and is pleased to have this distraction behind him.”

A lawyer for Mr. McConney could not immediately be reached for comment.

Mr. Trump, a Republican, has not been accused of a crime and has criticized the probe as a politically motivated fishing expedition by the district attorney, Cyrus R. Vance Jr., a Democrat. The Trump Organization declined to comment on Thursday, as did the district attorney’s office.

The district attorney’s office has long wanted Mr. Weisselberg’s help in its comprehensive probe of Mr. Trump, and the accusations against him might intensify the pressure on him. An indictment released on July 1 accused Mr. Weisselberg of failing to pay taxes on $1.7 million worth of goodies, including leased Mercedes-Benzes, bonuses and a rent-free apartment.

Mr. Trump also personally paid private school tuition for Mr. Weisselberg’s grandchildren, and Mr. Weisselberg requested that the notations “per Allen Weisselberg” be erased from the ledger recording the checks, according to the indictment.

Mr. Weisselberg pled not guilty. He remains employed at the Trump Organization, but he has been removed from senior duties at the company’s subsidiaries.

A case against Mr. Calamari, who resided in a Trump building in Manhattan and drove a Mercedes-Benz leased through the firm, could be tough for prosecutors.

Unlike Mr. Weisselberg, an accountant who managed the company’s finances for decades, Mr. Calamari is not a financial specialist and was not responsible for the Trump Organization’s accounting department. He also may argue that his job required him to live close to the company’s offices in Trump Tower, and while fringe perks are normally taxable, there are some exceptions.

The focus on fringe perks is one facet of a bigger inquiry into whether Mr. Trump and the corporation misrepresented property valuations to gain certain loans and tax benefits, among other potential financial crimes. It inquiry has continued, however it is unclear whether that will lead to any charges.

The corporation has denied any wrongdoing.