An investigation into Allen Weisselberg, the Trump Organization’s finance chief, appears to be heading into its final stages as prosecutors increase pressure on him.
The Manhattan district attorney’s office appears to have entered the final stages of a criminal tax investigation into Donald J. Trump’s long-serving chief financial officer, Allen H. Weisselberg, setting up the possibility he could face charges this summer, according to people with knowledge of the matter.
In recent weeks, a grand jury has been hearing evidence about Mr. Weisselberg, who is facing intense scrutiny from prosecutors as they seek his cooperation with a broader investigation into Mr. Trump and the Trump Organization, the people with knowledge of the matter said. The prosecutors have obtained Mr. Weisselberg’s personal tax returns, the people said, providing the fullest picture yet of his finances.
Even as the investigation has heated up, it remains unclear whether the prosecutors will seek an indictment of Mr. Weisselberg, which would mark the first criminal charges stemming from the long-running financial fraud investigation into Mr. Trump and his family company.
The investigation into Mr. Weisselberg focuses partly on whether he failed to pay taxes on valuable benefits that Mr. Trump provided him and his family over the years, including apartments and leased cars as well as tens of thousands of dollars in private school tuition for at least one of his grandchildren. In general, those types of benefits are taxable, although there are some exceptions, and the rules can be murky.
For months, prosecutors working for District Attorney Cyrus R. Vance Jr., a Democrat, have sought to pressure Mr. Weisselberg into cooperating with their investigation into Mr. Trump, and any deal could turn the trusted executive into a star witness against the former president. For now, Mr. Weisselberg appears to have rebuffed Mr. Vance’s office and continues to work at the Trump Organization.
The district attorney’s office recently questioned Mr. Weisselberg’s top lieutenant, Jeffrey S. McConney, before a special grand jury hearing evidence in the Trump inquiry, people with knowledge of the matter have said. The testimony was the first sign that the grand jury was hearing evidence about Mr. Weisselberg.
When hoping to turn an insider into a cooperating witness, prosecutors often seek leverage over the person, and then typically offer leniency in exchange for testimony or assistance.
The Trumps have long been able to count on Mr. Weisselberg’s fealty. After beginning his career working for Mr. Trump’s father, Mr. Weisselberg has served as the Trump Organization’s financial gatekeeper for more than two decades.
Even if Mr. Weisselberg chooses not to assist the investigation into his boss, charges against him could portend trouble for Mr. Trump, signaling that the prosecutors have identified what they believe is misconduct at his family business.