Mr. Trump won the presidency by portraying himself as a political outsider with the business acumen to shake up Washington. But the company whose name he made famous on his reality television show, “The Apprentice,” might eventually be associated as much with criminal charges as it is with the hotels and golf courses that bear his name. If the company is found guilty, it could face fines or other penalties.
In the next phase of the broader investigation into Mr. Trump and his company, the prosecutors are expected to continue scrutinizing whether the Trump Organization manipulated property values to obtain loans and tax benefits, among other potential financial crimes, according to people familiar with the matter.
Letitia James, the New York attorney general, said in a statement that the investigation will continue.
An accountant who began his career working for Mr. Trump’s father nearly a half-century ago, Mr. Weisselberg has served as the Trump Organization’s financial gatekeeper for more than two decades and recently ran the business with Mr. Trump’s adult sons while Mr. Trump was in the White House.
Famously hard-working — he once said he took “no vacations” — Mr. Weisselberg gained an unparalleled view into the inner workings of the company and its bare-knuckled brawls with business partners. Mr. Weisselberg “knows of every dime that leaves the building,” Corey Lewandowski, a former Trump campaign official, wrote in the book he co-authored, “Let Trump Be Trump.”
Mr. Weisselberg, who is 73 years old, 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.