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The two ongoing probes of the Trump Organization – one led by New York’s attorney general and the other by the Manhattan district attorney – are reportedly investigating whether Mr Calamari received fringe benefits, such as cars and apartments, from the company without paying taxes.
Experts say the inclusion of Mr Calamari shows the investigations are widening their net on the fringe benefits issue. Prosecutors had already been looking into whether the family of Allen Weisselberg, the Trump Organization’s chief financial officer, received such benefits, according to CNN.
Neither Mr Calamari nor Mr Weisselberg have been accused of any wrongdoing. But receiving tax-free perks can potentially be a crime, experts say, and prosecutors could use the threat of any possible charges to pressure either man into testifying against Mr Trump.
So far, however, that pressure has not shown any signs of working on Mr Weisselberg. According to The Washington Post, the CFO is still showing up for work at Trump Tower, and investigators have complained of his lack of cooperation.
Last month, CNN revealed that both New York probes have been investigating the longtime Trump executive. But according to the Post, investigators believe he still speaks regularly with Mr Trump. On 14 June, the former president’s birthday, the newspaper spotted Mr Weisselberg entering Trump Tower at a time when Mr Trump was in the building.
Jennifer Weisselberg, the CFO’s former daughter-in-law, has reportedly been cooperating with investigators since last fall. She has alleged that Mr Weisselberg and Mr Trump helped fund the lavish lifestyle that she and her ex-husband Barry Weisselberg, who worked at the Trump Organization, enjoyed. This reportedly included tuition payments at New York private schools and rent-free stays in Trump Organization apartments, which could raise potential red flags for investigators.
“I know for a fact Donald wrote those checks,” she told CNN in April.
The Manhattan district attorney, Cyrus Vance, convened a grand jury last month to decide whether to indict the former president.
Mr Trump has denounced the investigations as baseless and politically motivated.
“This is a continuation of the greatest Witch Hunt in American history,” he said after the grand jury was announced. “It began the day I came down the escalator in Trump Tower, and it’s never stopped.”
The Independent has contacted the Trump Organization for comment, but has not yet heard back.