In February 2019, former Trump attorney Michael Cohen testified in front of Congress that his old boss had inflated the values of assets for insurance purposes. Cohen listed names of other individuals within the Trump Organization who allegedly knew about such practices. Among those names: Matthew Calamari, Trump's ex-bodyguard who currently serves as the Trump Organization's COO. Now, Calamari's name is in the news again, with sources telling the Wall Street Journal that prosecutors are looking into whether the executive, who's worked for the company for nearly 40 years, received tax-free perks along with his regular paycheck. Manhattan District Attorney Cyrus Vance Jr.'s team is working with the office of New York Attorney General Letitia James in a broad criminal investigation into the Trump Organization and its officers regarding possible bank, tax, and insurance fraud, with Calamari the latest apparent subject of interest.
Per sources and public records, Calamari has lived for years in a luxury apartment at Trump Park Avenue, owns a Long Island home, and drives a Mercedes leased through the company. His son, Matthew Calamari Jr., who's the company's corporate director of security, lives in Trump Parc East, across from Central Park. "It was a corporate apartment, so we didn't have rent," Barry Weisselberg, son of Trump Org CFO Allen Weisselberg, said in a 2018 divorce deposition regarding that residence, which he also lived in. Sources say the Calamaris have been advised by prosecutors to get their own attorney—a signal the heat is turning up on them personally, per the Journal, which notes that neither the Calamaris nor the Weisselbergs have yet been accused of any wrongdoing. (Read more Donald Trump stories.)