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Lawyers for Mr. Weisselberg, who is 73 years old, and the Trump Organization could not immediately be reached for comment. Mr. Trump has long attacked Mr. Vance’s investigation as a partisan “witch hunt.” Earlier this week, he called the fringe benefits that his company provided to employees “things that are standard practice throughout the U.S. business community, and in no way a crime.”

Now that he faces charges, Mr. Weisselberg still could cooperate with the prosecutors. If he ultimately pleads guilty and strikes a deal, he could do considerable damage to Mr. Trump, who for decades has depended on his unflinching loyalty, once declaring with “100 percent” certainty that Mr. Weisselberg had not betrayed him.

The two started working together closely in the late 1970s, with Mr. Weisselberg putting in time on nights and weekends to handle projects for Mr. Trump, the ambitious son of his boss, Fred Trump. Mr. Weisselberg said in a 2015 deposition that he had been helping with Mr. Trump’s tax returns since at least the 1990s, when Mr. Trump made him the organization’s chief financial officer.

Mr. Weisselberg has remained steadfastly loyal to the company even as his own name surfaced during congressional and federal investigations into Mr. Trump. While Mr. Weisselberg was never a target of those investigations, he has long been a central focus of the district attorney’s inquiry, which began in August 2018.

As the prosecutors have zeroed in on the benefits he and his family received from Mr. Trump, they have examined tens of thousands of dollars in private school tuition for one of Mr. Weisselberg’s grandchildren, a rent-free apartment on the Upper West Side of Manhattan and leased Mercedes-Benz vehicles. Mr. Weisselberg’s wife also received her own leased Mercedes.

Mr. Weisselberg was not the only senior company executive to receive similar perks. Until 2018, when the company reined in the benefits, it provided a number of employees with Mercedes-Benzes.

Those types of benefits are generally taxable, though there are exceptions, and the tax rules can be murky.