Donald Trump’s business brought him international fame, a hit television show, a presidential résumé and, on Thursday, an indictment in New York State Court that could damage both his financial and political futures.

The full impact on Trump’s business of the 10 felony counts brought against it by Manhattan District Attorney Cyrus Vance Jr, D – as well as 15 felony counts against his chief financial officer – remains to be seen. The company and CFO Allen Weisselberg pleaded not guilty to all the charges. Trump was not charged in the case.

The indictment comes after nearly six years of his company enduring one blow after another wrought by Trump’s political career. That trajectory began with the loss of merchandising deals during the early days of his first campaign, continued with the loss of branding and management agreements during his presidency, and culminated with a wave of partners vowing to longer do business with him following the Jan. 6 attack on the Capitol.

Trump will remain a wealthy man regardless of whether his company is convicted of any of the charges. But the indictment adds to a growing pile of uncertainties about his company that experts say makes its future less clear than at any time since Trump’s much publicized collapse in Atlantic City and New York in the 1990s.

If convicted, the company could face hefty fines or other court-imposed penalties, according to legal experts. A felony conviction can complicate companies’ efforts to secure bank loans or even municipal licenses to sell alcohol or get construction permits.

Trump – referred to as the “former CEO” by prosecutors – has relocated to Florida. His two eldest children, Donald Trump Jr. and Ivanka Trump, have followed his path out of business into the political sphere. And some of his top properties have suffered severe drops in revenue, with more than $300 million in debts to refinance or pay off in the next few years.

“The immediate prosecution isn’t going to threaten to wipe out the company,” said Michael D’Antonio, who wrote two biographies of Trump. “But what it does is open the possibility of so many secrets spilling out that the ramifications could last for years. It could be five or six years before all of this gets sorted. And that’s a long time for a company that’s built, in large measure, on the value of its reputation.”

After the charges were announced, Trump issued a statement calling the indictment a “political witch hunt by the Radical Left Democrats.” The former president has asked people around him about the prospect of a casino at his Doral resort in South Florida and has touted the revenue of his golf courses, according to two people who have talked to him but were not authorized to share private conversations. He has “compartmentalized” his business and political endeavors in the words of an adviser, going to his Trump Tower office in New York two days a week, usually arriving on Sunday evening and leaving late Tuesday.

Still, several advisers said he was more interested in his political future than business. The company has made few moves publicly since Trump left the White House in January, although it has sued New York City over a canceled contract and some office tenants over allegedly unpaid rent. The company is also again trying to sell the federal lease to its D.C. hotel but even that it declined to announce.

The company issued a statement saying Vance “will try to convince the public that these charges are of great significance. However, everyday New Yorkers and Americans know exactly what this is: an inappropriate use of a local prosecutor’s vast and unchecked power to target a political opponent. While the District Attorney pursues this political vendetta, The Trump Organization will continue to focus on our thousands of hard working and outstanding employees who, day in and day out, provide unparalleled service and experiences for our customers and members at our award-winning properties.”

Trump Organization representatives did not respond to questions about the company.

D’Antonio and another Trump biographer, Gwenda Blair, both said the indictment of the Trump Organization comes during what appears to be the company’s most difficult moment since Trump’s financial crash in the early 1990s.

During that period, Trump found himself hundreds of millions of dollars in debt, and lost control of prized assets – including an airline, a yacht and New York’s Plaza Hotel. His business empire did not fully recover for a decade, until Trump gained television fame and made tens of millions as the star of NBC’s “The Apprentice.”

The financial picture for Trump today, based on his government disclosures, is dramatically better than it was then. On his most recent financial disclosure form, Trump reported around $300 million in income for 2020. But experts and former employees say the reputation of his brand among consumers and potential business partners is arguably worse.

Barbara Res, a top construction executive at the Trump Organization from 1980 to 1998, said Trump was already facing a problem caused by his political career: His company is still built around the old gold-plated luxury brand, aimed at wealthy urban dwellers and tourists. But his political career alienated most of that demographic. Now, Res said, “Most of his [company’s] brand talks to people who are not his supporters.”

Res said she expects the indictment will further restrict Trump’s ability to attract partners and lenders. “Why would you want to be associated with Trump if you didn’t have to be?” Res said Thursday. “I think it will have a dramatic impact on the company.”

That impact will almost certainly be more severe if the company or Weisselberg, or both, are convicted of the felonies Vance and New York Attorney General Letitia James, D, leveled in court Thursday.

Prosecutors charged the company with what they called a 15-year “scheme to defraud” the government of taxes through what they described as a wide-ranging effort to hide compensation provided to Weisselberg and other employees, including apartments, luxury cars, bonuses and private school tuition for employees’ children.

An attorney for the company, Alan Futerfas, blasted the case as “politically driven” and suggesting that bringing criminal charges over allegedly untaxed benefits was extremely unusual.

“These type of cases are typically resolved in a civil context. Why? Because the law on compensation, on fringe benefits, is murky, it’s difficult, it’s complex, you could have experts disagree,” Futerfas said.

Legal experts with experience in high-stakes corporate cases agreed that bringing such charges was unusual but nevertheless, they may still have merit.

Barbara McQuade successfully brought federal charges against Volkswagen in one of the widest-ranging corporate prosecutions. The carmaker pleaded guilty to developing software to cheat emissions tests.

Prosecutors in such cases need to identify a high-ranking official who has the requisite responsibility over the actions being taken and has shown intent to violate the laws, she said. That’s what makes Weisselberg so important to prosecutors’ case.

“The Trump Organization is small. It has a really small control group. You can imagine that individual executives would be acting with knowledge and intent,” said McQuade, now a University of Michigan law professor.

It’s “fairly unusual” to prosecute this type of crime, said Columbia University law professor John Coffee Jr. But he said: “That’s not a defense. Just because a prosecutor normally goes after other bigger crimes, that’s not a defense.”

Coffee also said he could see additional charges being filed as the prosecution tries to coax Weisselberg to cooperate in a prosecution of Trump, an effort that has so far been unsuccessful.

“This may be just the beginning to become applying strong pressure on Mr. Weisselberg to flip him,” he said.

Banking experts said an indictment alone is unlikely to immediately affect Trump’s existing loan agreements or contracts. A spokesman for Deutsche Bank, which holds the vast majority of Trump’s debt, declined to comment. A spokeswoman for the General Services Administration, the agency that holds Trump’s D.C. hotel lease, also declined to comment.

If Weisselberg, 73, were to unexpectedly leave the company, whether for reasons related to the case or not, D’Antonio said, it could cause a major disruption. He said Weisselberg has effectively run the business with Trump for several decades, managing the details and the finances while Trump built his brand and cut deals.

“I think of Weisselberg and Donald as brothers who were brought into the company at the same time. And one was the outside man and one was the inside man,” D’Antonio said. He said Weisselberg’s inside-man role was especially important because of the company’s complex finances: The Trump Organization is a web of hundreds of interrelated limited liability companies, making it unusually difficult to run for a relatively small company.

“It’s complex – but not huge,” D’Antonio said of the company. “It was Weisselberg’s job to keep everything straight.”

Daniel Goldman, a former assistant U.S. attorney and lead House impeachment lawyer in 2019, said Trump’s political framing of the charges is focused on business partners, lenders and others who impact the former president’s bottom line.

“He is trying to take the attack in belittling these charges so they won’t end their relationship with him,” Goldman said. “He’s basically trying to save his company.”

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