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

• Trump Org. executives may cooperate with prosecutors if facing criminal charges, a former EVP said.
• Allen Weisselberg and Matthew Calamari can't stomach prison time, Barbara Res said.
• Res said they don't have "black hearts" like former Trump aides Paul Manafort and Roger Stone.

A former Trump Organization executive said two top employees 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 believed that Allen Weisselberg and Matthew Calamari wouldn't be able to stomach prison time, nor risk criminal charges against their sons who 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 said 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, The Washington Post reported.

People with knowledge of the matter told The New York Times that prosecutors may announce criminal charges against Weisselberg, the Trump Organization's 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, who is also a Trump Organization employee. Jennifer Weisselberg, Barry'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, The Wall Street Journal reported. 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 said 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.

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 Allen Weisselberg holds Trump in high esteem, but would do anything to protect his son.

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 Trump loyalists Roger Stone and Paul Manafort.

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 believed that 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 said, 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."

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 believed that 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."