One sentence in the Trump Organization indictment suggests more charges are coming, former prosecutor says

donald trump rally worried
Former U.S. President Donald Trump speaks at a rally at the Sarasota Fairgrounds on July 3, 2021 in Sarasota, Florida, United States.

  • The Manhattan DA’s Trump Organization investigation is still ongoing after last week’s indictments.
  • Prosecutors described its CFO as “one of the largest individual beneficiaries” of an alleged tax scheme.
  • The language suggests people other than Allen Weisselberg benefited and could be charged later.
  • See more stories on Insider’s business page.

One sentence in the Manhattan District Attorney’s 15-count indictment against the Trump Organization suggests more people affiliated with the ex-president’s family company could face charges in the future, according to a former prosecutor.

Thursday’s indictment alleged the Trump Organization and CFO Allen Weisselberg participated in a yearslong scheme to avoid paying taxes on $1.7 million worth of compensation. Both Weisselberg and attorneys for the Trump Organization pleaded not guilty to the charges against them.

Randy Zelin, a former New York state prosecutor, told Insider the charging documents included a sentence that offered a clue about other people who may have been involved in the alleged tax scheme.

“One of the largest individual beneficiaries of the defendants’ scheme was Allen Weisselberg,” the indictment reads.

Zelin, now a defense attorney at Wilk Auslander LLP, said prosecutors’ use of the word “individual” suggests other people – not just corporations – benefited from the Trump Organization’s alleged tax avoidance scheme.

“The government could have said he was the only one, right? The government didn’t have to use the word ‘individual,'” Zelin said. “The fact that the government inserted the word ‘individual’ means that there may be others who enjoy perks.”

“The fact that the government said ‘one of the largest’ – that by its very nature means other people were doing the same or doing similar,” he added.

The investigation into the Trump Organization is ongoing. A special grand jury is scheduled to sit until November, examining issues like whether the company kept two sets of books, if it broke laws by facilitating a hush-money payment to adult film star Stormy Daniels, and whether anyone other than Weisselberg got untaxed benefits.

Trump Organization chief financial officer Allen Weisselberg exits after his arraignment hearing in New York State Supreme Court in the Manhattan borough of New York City, New York, U.S., July 1, 2021.
Trump Organization chief financial officer Allen Weisselberg in court.

The indictment describes an ongoing tax avoidance scheme that prosecutors allege began in 2005. Former President Donald Trump personally led the company until 2017, and then turned over leadership to Weisselberg and his two eldest sons, Eric and Donald Trump Jr., who have disparaged the investigation as politically motivated.

Zelin noted that the Trump Organization closed ranks around Weisselberg after he was charged, suggesting the executive wasn’t a rogue actor in the alleged tax avoidance scheme.

“If he had done this on his own, he would have then have been cheating the Trump Organization,” Zelin said. “Not only wasn’t he terminated, not only was he not suspended pending further investigation, not only was he not suspended once he was indicted – but apparently he’s gone back to work since his indictment.”

Manhattan prosecutors have sought Weisselberg’s cooperation in their investigation, and Zelin said the charges against him could help flip more people from Trump’s orbit.

Matthew Calamari, the Trump Organization’s chief operating officer who lived in company-owned apartments, is under scrutiny as well. And Ivanka Trump, who appeared to take a tax-deducted consulting fee from the company despite being one of its executives, according to a New York Times investigation of tax filings, may also be at legal risk.

“There’s certainly a lot of clues that would suggest that this indictment is just the beginning, rather than the end,” Zelin said.

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Trump Organization COO Matthew Calamari won’t face criminal charges this week, his lawyer says

Matthew Calamari
Matthew Calamari.

  • Trump Organization executive Matthew Calamari won’t be charged this week, his lawyer says.
  • Manhattan prosecutors are investigating him and his son as part of their probe into the company.
  • Prosecutors are expected to bring some charges in their investigation as soon as this week.
  • See more stories on Insider’s business page.

The office of Manhattan District Attorney Cyrus Vance Jr. will not bring charges against Trump Organization COO Matthew Calamari this week as part of its wide-ranging criminal investigation into the former president’s company finances, according to Calamari’s lawyer.

Nicholas Gravante Jr., who represents both Calamari and his son, Matthew Calamari Jr., the Trump Organization’s head of security, said that he doesn’t expect either of them to be charged soon.

“Not withstanding whatever criminal charges may or may not be brought against others at this time, I do not expect charges to be brought against either of my clients,” Gravante told Insider on Tuesday.

Prosecutors in Vance’s office are expected to bring charges in the case as soon as this week. A representative for the DA’s office declined Insider’s request for comment.

For two years, the Manhattan DA has been investigating whether the Trump Organization broke tax, bank, and insurance laws by misrepresenting the value of its properties.

Prosecutors are also investigating whether particular executives took benefits like apartments without paying the appropriate taxes on them, or broke state finance laws by facilitating hush-money payments to adult film actress Stormy Daniels, who claimed to have an affair with the former president.

Ronald Fischetti, an attorney representing Trump in the case, told Politico that prosecutors assured him Trump would not personally be charged in the first indictment. The DA’s office is reportedly weighing whether to bring charges against the Trump Organization or CFO Allen Weisselberg as well.

Prosecutors have empaneled a special grand jury to weigh bringing indictments. The grand jury is expected to run through at least November, and may still bring charges against Calamari, other executives, the Trump Organization, or Trump himself in the future.

The Wall Street Journal reported earlier in June that the DA’s office was investigating whether the Calamaris, who both live in apartment buildings managed by the Trump Organization, received tax-free benefits.

Neither Calamari is believed to have a role in evaluating properties or preparing taxes for the company.

Prosecutors advised the Calamaris to hire their own attorney, according to the Journal, which reported they had previously been represented by an attorney who had other clients at the Trump Organization.

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Former Trump Organization executive says Trump cultivates loyalty by giving jobs to his employees’ children

donald trump outside trump tower in nyc
Former U.S. President Donald Trump leaves Trump Tower in Manhattan on May 18, 2021 in New York City.

  • Trump cultivated loyalty among his employees by hiring their kids, a former executive said.
  • Two executives under scrutiny in the Manhattan DA investigation have kids who work at the Trump Organization.
  • Neither CFO Allen Weisselberg nor COO Matthew Calamari appear to be cooperating with prosecutors.
  • See more stories on Insider’s business page.

Donald Trump hires the children of his Trump Organization employees as a reward and as added leverage in case they ever consider turning on him, a longtime former executive told Insider.

Those family hires pose a potential problem for prosecutors in the Manhattan District Attorney’s Office, which is investigating potential tax, bank, and insurance fraud at the Trump Organization. Prosecutors have sought the cooperation of Allen Weisselberg, the company’s chief financial officer, and reportedly investigated Matthew Calamari, its chief operations officer.

Both executives have sons who also work for the Trump Organization. Barry Weisselberg operated the Trump Organization-run Wollman Rink in Manhattan’s Central Park, while Matthew Calamari Jr. runs security operations for the company.

Barbara Res, who served as an executive vice president at the Trump Organization for nearly 20 years, told Insider that Trump’s employment of Barry Weisselberg may help explain why his father still isn’t cooperating with prosecutors.

“Weisselberg still isn’t cracking from what I understand,” Res told Insider on Thursday. “What kind of loyalty is that? That’s incredible loyalty. I don’t know what Trump is promising him, but I think that Trump has engendered that kind of loyalty from Weisselberg, and I think probably Calamari too.”

Court filings and public comments suggest the Manhattan District Attorney’s Office is examining whether the Trump Organization, individual executives, or Donald Trump himself broke laws by manipulating property values to pay little in taxes while receiving favorable insurance and bank loan rates.

Prosecutors also appear to be examining whether executives received tax-free perks like apartments, cars, and school tuition. The district attorney’s office empaneled a special grand jury and may announce some charges as soon as this week.

‘Not only would he get fired – his son would lose his job’

Res led construction projects at the Trump Organization between 1980 and 1998, and wrote a book about Trump’s leadership and management style. She noted she doesn’t have firsthand knowledge of either the Manhattan District Attorney’s or the New York Attorney General’s office’s investigations into the Trump Organizations, and has not been contacted by prosecutors from either one.

As many property developers do, Res said, Trump donated to politicians as a quid-pro-quo. He also has given gifts and perks to employees for decades, which she also saw as a transactional relationship.

“He loved to give things, especially if it didn’t cost him anything,” she said. “He loved to give things to people that engender their support or their loyalty.”

He gave her tickets to the US Open every year, she said, to build goodwill – and then asked her to do things she shouldn’t. She had to “say no to him a lot of times,” she said.

“I know from my experience with Trump that he would tell us to do things that were not legal, and we wouldn’t do it,” Res said. “So there’s no doubt in my mind that Trump would people continue to ask people to do things that are not legal.”

donald trump in black car outside trump tower manhattan nyc
Former U.S. President Donald Trump leaves Trump Tower in Manhattan on March 9, 2021 in New York City.

Over the years, Res said, Trump’s view of transactional relationships through corporate perks grew, intertwining the personal lives of his tightly knit team with his company’s interests.

Jennifer Weisselberg, the former daughter-in-law of Allen Weisselberg and a cooperating witness in investigations into the Trump Organization, previously told Insider that the company provided her home and paid for her kids’ tuition. Prosecutors have also scrutinized the finances of Barry Weisselberg, she said.

“They want you to do crimes and not talk about it and don’t leave,” Jennifer Weisselberg said. “It’s so controlling.”

“Because if you want to leave and make the same money – you live there,” she added. “If you want to leave, where are you going to live?”

matthew calamari donald trump jr
Donald Trump Jr. and Matthew F. Calamari in 2012.

Those sorts of perks, like providing apartments, and favors, like hiring children, makes it harder for executives to say no to Trump when he gives them distasteful instructions, Res said.

“So if Donald told Matt [Calamari] to do something, and he said ‘no,’ not only would he get fired – his son would lose his job,” Res said.

Res recounted a story where Trump was upset that a man had set up a cart to sell things outside Trump Tower in Manhattan, and asked Calamari to get rid of him.

“Matt went out there and said, ‘We don’t want you here,’ and the guy said, ‘Screw you,'” Res recalled. “So that night, all his stuff was moved out of there and put somewhere else.”

But the man with the cart returned – on several occasions, even as Calamari repeatedly moved the stand somewhere else, Res said.

“Finally – I can’t imagine what Matt told him – but Matt either gave him money or threatened him,” Res said. “Because the guy never came back.”

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Trump Organization executives can’t stomach prison time and may flip if faced with criminal charges, former EVP says

donald trump in black car outside trump tower manhattan nyc
Former U.S. President Donald Trump leaves Trump Tower in Manhattan on March 9, 2021 in New York City.

  • Top Trump Organization executives may cooperate with prosecutors if facing criminal charges, a former EVP at the company said.
  • Allen Weisselberg and Matthew Calamari can’t stomach prison time, according to Barbara Res.
  • Res said they don’t have “black hearts” like former Trump aides Paul Manafort and Roger Stone.
  • See more stories on Insider’s business page.

A former Trump Organization executive says that two top employees reportedly under scrutiny in the Manhattan district attorney’s investigation into the company might cooperate if prosecutors introduce criminal charges against them.

Barbara Res, a former executive vice president at the Trump Organization, told Insider she believes Allen Weisselberg and Matthew Calamari wouldn’t be able to stomach prison time, nor risk criminal charges against their sons – both of whom are employed at the company.

“If you introduce the notion of criminal charges against any one of them, or their children, you change the game completely,” she said.

Res noted she doesn’t have firsthand knowledge of the Manhattan District Attorney’s or New York Attorney General’s investigation, and hasn’t been contacted by prosecutors from either office.

For two years, investigators have examined whether the Trump Organization or its executives committed tax, bank, or insurance fraud. The Manhattan DA’s office gave the company a Monday afternoon deadline to complete its arguments against being charged, according to the Washington Post.

People with knowledge of the matter told The New York Times that prosecutors may announce criminal charges against Weisselberg, the Trump Organization chief financial officer and the company and family bookkeeper of 40 years, as soon as this week.

Manhattan prosecutors have sought Weisselberg’s cooperation and examined the finances of his son, Barry Weisselberg, who is also a Trump Organization employee. Jennifer Weisselberg, Barry Weisselberg’s ex-wife and a cooperating witness in the investigation, previously told Insider that the couple received tax-free perks from the company.

Prosecutors also told Calamari, the Trump Organization’s chief operating officer, to hire an attorney, according to the Wall Street Journal. They’ve asked about the possibility that Calamari skirted taxes on company perks, the Journal reported.

The former executive said Weisselberg and Calamari can’t stomach prison time

Res worked for the Trump Organization between 1980 and 1998, overseeing construction projects. During the 2020 election, she wrote a book about Trump and what she described as his condescending treatment of employees.

She told Insider that Weisselberg and Calamari, both colleagues during her years at the company, have been loyal to Trump. But she thinks neither could stomach prison time.

“It’s a very different thing than just doing a favor for Trump or engendering his admiration,” she said. “Now you’re asking people to take their loyalty to Trump, and keep it, even though they may have to go to jail for it – or worse, their child may have to go to jail.”

“I don’t know that either Calamari or Weisselberg can do that,” she added.

Matthew Calamari
Matthew Calamari.

Ronald Fischetti, an attorney representing the Trump Organization, told NBC News on Friday that Allen Weisselberg was not cooperating with prosecutors, who wanted him to implicate Trump in wrongdoing.

“They could not get him to cooperate because he would not say that Donald Trump had knowledge or any information that he may have been not deducting properly the use of cars or an apartment,” he said.

Jennifer Weisselberg previously told Insider she expected her former father-in-law to cooperate. She said that Allen Weisselberg holds Trump in high esteem, but would do anything to protect his son.

donald trump jr allen weisselberg
Donald Trump, Allen Weisselberg, and Donald Trump Jr. in 2017.

Legal experts told Insider that Weisselberg may be holding out for as long as possible to increase his leverage and ensure he won’t have to go to prison.

Manhattan prosecutors have empaneled a special grand jury that may bring charges against the Trump Organization, particular executives, or Trump himself. They have not made any accusations of wrongdoing at this point, and it’s possible no charges will be brought.

Trump himself has repeatedly denied any wrongdoing and has described the investigations into his conduct as politically motivated.

Top Trump Organization brass aren’t ‘evil’ like Paul Manafort and Roger Stone, the former executive said

Res drew a distinction between Weisselberg and Calamari, and Roger Stone and Paul Manafort, both Trump loyalists.

Manafort, a longtime Republican operative who led Trump’s 2016 presidential campaign, was convicted of numerous crimes including fraud and witness tampering. Stone, another longtime Republican operative who worked for Trump, was convicted of lying to the FBI and witness tampering.

Res said she believes Manafort and Stone refused to cooperate with prosecutors because they knew Trump would pardon them. Trump pardoned Manafort and commuted Stone’s prison sentence shortly before the end of his presidential term.

Weisselberg and Calamari, she pointed out, have no shot at a pardon: They’re being investigated under state law in New York, where the governor is a Democrat.

“There is no pardon,” Res said. “There’s no get out of jail free card. It’s different.”

Paul Manafort in 2019.

Res, who’s known Calamari and Weisselberg for decades, said neither of them had the inherent darkness of the Trump loyalists who were convicted.

“Manafort and Stone – Those guys are animals. They have evil hearts,” she said. “I knew Matt very well, and I know Allen pretty well. I don’t see them as having evil hearts like Trump and Manafort and Roger Stone.”

Neither Weisselberg nor Calamari have made public statements or been photographed much since Trump took office. Res said she believes the two executives are likely uncomfortable with the attention around the investigation.

Now, reporters are looking into Weisselberg’s and Calamari’s personal lives, apartments, and grandchildren’s schools.

“We hardly heard their names for four years when Trump was president,” Res said. “Now all of a sudden they’re in every paper.”

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