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. James Devaney/GC Images
  • 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. James Devaney/GC Images via Getty Images

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. Bobby Bank/Getty Images

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.”