A long-running criminal investigation into Donald J. Trump and his family business is reaching a critical phase as Cyrus R. Vance Jr., the prosecutor overseeing the inquiry, enters his final weeks as Manhattan district attorney.
Mr. Vance’s prosecutors have issued new subpoenas for records about Mr. Trump’s hotels, golf clubs and office buildings. They recently interviewed a banker employed by Deutsche Bank, Mr. Trump’s top lender. And earlier this month, they told a top Trump executive who had been under scrutiny, Matthew Calamari, that they did not currently plan to indict him in the purported tax-evasion scheme that led to charges against Mr. Trump’s company and its chief financial officer.
The developments, described by people with knowledge of the matter, show that the Manhattan prosecutors have shifted away from investigating those tax issues and returned to an original focus of their three-year investigation: Mr. Trump’s statements about the value of his assets.
In particular, the people said, the prosecutors are zeroing in on whether Mr. Trump or his company inflated the value of some of his properties while trying to secure financing from potential lenders. If Mr. Vance’s office concludes that Mr. Trump intentionally submitted false values to potential lenders, prosecutors could argue that he engaged in a pattern of fraud.
Mr. Trump and his company have denied wrongdoing, calling the inquiry a politically motivated witch hunt by Mr. Vance, a Democrat. His prosecutors are working with the office of the New York State attorney general, Letitia James, also a Democrat, who is running for governor and has been a vocal critic of Mr. Trump.
The investigation is playing out as Mr. Trump continues to wield enormous influence over the Republican Party and flirts with another presidential run in 2024. It has yet to hamper his political standing and could even energize his base, though the inquiry could also serve as a costly distraction.
It is unclear whether any new charges will be brought, but if they are, it could be difficult to prove that Mr. Trump or his company defrauded their lenders. One challenge is that the lenders are sophisticated financial institutions that most likely conducted their own assessments of Mr. Trump’s property values without relying entirely on him.
Still, Mr. Vance’s prosecutors have issued a flurry of subpoenas in recent months.
At least one subpoena issued this summer to Mr. Trump’s company, the Trump Organization, demanded information about how the company valued various assets, according to the people, who all spoke on the condition of anonymity because they were not authorized to discuss the matter.
The company is resisting turning over some documents, a matter that is the subject of sealed litigation in Manhattan.
The Deutsche Bank employee, a banker in the division that works with Mr. Trump, also recently met with prosecutors in Mr. Vance’s office to answer their questions, the people said.
The bank has issued hundreds of millions of dollars in loans to Mr. Trump over the years, including for his hotels in Chicago and Washington and his Doral golf resort in Florida.
Last year, during a relatively early phase in the investigation, the prosecutors questioned Deutsche Bank employees about the lender’s general procedures for making loan decisions.
This summer, the prosecutors diverged from that focus on valuations when they indicted the Trump Organization and its long-serving chief financial officer, Allen H. Weisselberg, for unrelated tax crimes involving a scheme to pay off-the-books luxury perks to certain executives.
Mr. Vance’s office had also been weighing for months whether to indict Mr. Calamari, Mr. Trump’s former bodyguard who now serves as the organization’s chief operating officer, for failing to pay taxes on the same sort of perks.
But this month, after prosecutors pivoted back to the broader investigation, they told Mr. Calamari that they had “no present intention” to bring charges, his lawyer said.
“We believe that is the fair and just decision,” said the lawyer, Nicholas Gravante Jr., who had argued that Mr. Calamari was not involved in the company’s finances and relied on another Trump employee to prepare his taxes. “What the future holds in terms of the district attorney’s continuing investigation is anyone’s guess.”
Mr. Vance, who did not seek re-election for a fourth term this year, originally signaled that he wanted to decide whether to charge Mr. Trump before departing.
But he is running out of time.
He leaves office at the end of this year, and it might take prosecutors months to present a complex financial case like this one to a grand jury should they decide charges are warranted.
And so, after more than three years of investigating Mr. Trump in fits and starts, Mr. Vance may have to hand over the culmination of the case to his successor, Alvin Bragg.
In his first weeks in office, Mr. Bragg would face a monumental decision: whether to seek an indictment against a former American president.
Mr. Bragg, a former federal prosecutor who will be the first Black person to hold the office, campaigned in part on his aggressive record toward Mr. Trump, frequently mentioning the many times he had sued the Trump administration while serving in the state attorney general’s office.
Since winning the Democratic primary in June, Mr. Bragg has been more reserved. A spokesman for Mr. Bragg, Richie Fife, said that he intended to retain the team working on the Trump investigation, including two senior officials overseeing it, Mark F. Pomerantz and Carey Dunne, Mr. Vance’s general counsel who has been deeply involved in the case.
Mr. Bragg has not yet been briefed on the details of the investigation, Mr. Fife said. He takes office on Jan. 1.
Mr. Vance is one of three district attorneys investigating Mr. Trump or his company. Mr. Trump’s attempts to overturn Georgia’s election results last year are the subject of a criminal investigation in Atlanta. And the district attorney in suburban Westchester County, outside of New York City, has begun to examine financial dealings at a golf club Mr. Trump owns there.
The Westchester investigation has focused partly on whether the Trump Organization, while seeking to cut that club’s tax bill, falsely undervalued the property. The company has denied all wrongdoing and other golf course operators say that it is common in the industry to propose lowball figures when appealing property taxes.
At one point, Mr. Vance’s office similarly examined the company’s dealings with property tax authorities in New York City, but his prosecutors appear to have largely moved away from that effort.
They are instead focused now on the company’s statements to lenders, and have also examined some of its unsuccessful attempts to secure financing, the people said.
Lawyers for the Trump Organization likely will argue that property values are subjective and that Mr. Trump could not have duped Deutsche Bank because the lender, knowing Mr. Trump’s values were estimates and that he had a reputation for exaggerating his wealth, did its own analysis of his net worth.
People with knowledge of the relationship have said that after the bank came to believe that Mr. Trump was overvaluing some of his assets, it still decided to lend him money, concluding that he was a safe risk in part because he had more than enough money and other assets to personally guarantee the debt.
The Trump Organization is expected to soon sell the lease on the hotel in Washington and pay off Deutsche Bank’s loan to that property.
Mr. Vance’s investigation began in August 2018 with a focus on the company’s role in paying hush money to an adult film actress who said she had an affair with Mr. Trump.
The inquiry was first delayed for nearly a year at the request of federal authorities, who had been focused on some similar conduct, and then by an 18-month battle in which Mr. Trump sought to block the district attorney from obtaining his tax returns.
That bitter legal battle twice reached the United States Supreme Court before ending in victory for Mr. Vance’s office, which obtained millions of pages of Mr. Trump’s personal and corporate tax records and other financial documents.
Once the prosecutors obtained the records, they focused on pressuring Mr. Weisselberg to cooperate and turn on his longtime employer.
But Mr. Weisselberg rebuffed the prosecutors, a decision that led to his indictment in July, along with the Trump Organization.
By bringing the charges against Mr. Weisselberg and the company, the prosecutors chose to take what amounted to a detour, temporarily directing attention away from the wider investigation of Mr. Trump and his family business.
That case focused on what prosecutors described as a 15-year scheme at the Trump Organization to pay its executives off-the-books perks like free cars and apartments.
Prosecutors accused Mr. Weisselberg of receiving a rent-free apartment, private school tuition for his grandchildren and leased Mercedes-Benz vehicles for him and his wife.
He failed to pay taxes on $1.7 million of those benefits, according to the indictment, which charged him with grand larceny, tax fraud and other charges.
Mr. Weisselberg’s lawyers, Mary E. Mulligan and Bryan C. Skarlatos, have said that Mr. Weisselberg will fight the charges in court.
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