New York prosecutors have continued to pressure top Trump Organization executive Matthew Calamari to cooperate since charging the company and its chief financial officer earlier this month, according to a person familiar with the matter — the latest sign that the inquiry is continuing.
Calamari, the chief operating officer of the Trump Organization, is among a small group of top company executives with a close relationship to Trump who could possibly help prosecutors in their ongoing investigation.
Two years into the criminal investigation, prosecutors do not appear to have convinced anyone who works at the Trump Organization to cooperate against former President Donald Trump, according to a person familiar with the matter.
Prosecutors started talking to Calamari’s legal team before the indictment and have continued those discussions in the two weeks since it was unsealed by a Manhattan judge.
Prosecutors have charged the company’s chief financial officer, Allen Weisselberg, who has declined to cooperate, and subpoenaed Controller Jeff McConney to testify before the grand jury.
Under New York state law, McConney received immunity and is required to answer prosecutors’ questions.
Because Trump doesn’t use email, prosecutors would likely need a witness to testify about his intent and his understanding of the law to have grounds to charge him with a crime. Prosecutors have not charged Trump with any crime.
Calamari, and his son Matthew Calamari Jr., who also works at the company, have been under scrutiny by prosecutors over whether they properly paid taxes on subsidized rent and cars they received as benefits from the company, CNN has previously reported.
The Calamaris weren’t indicted earlier this month when the Manhattan district attorney’s office charged the company and Weisselberg, with a 15-year alleged tax scheme, saying they systematically avoided paying payroll taxes and income taxes on fringe benefits including rent-free apartments, cars and private school tuition.
Both the company and Weisselberg pleaded not guilty.
The lawyer representing the Calamaris, Nicholas Gravante, dismissed the idea that the elder Calamari had anything to offer prosecutors in their ongoing investigation.
“This is a financial investigation. My client has nothing to do with the financial running of the company,” Gravante said. “He is the chief operating officer. He is involved with security, doormen, building managers, construction, superintendents. He manages security and operations; he is not a financial person. This notion that he could cooperate is entirely speculative — cooperate as to what?”
A spokesman for the New York district attorney’s office declined to comment for this story.
Loyalist who may have little incentive to cooperate
Trump discovered Calamari at the 1981 US Open tennis tournament after he liked the way Calamari, working security, handled hecklers at a match.
Calamari got his start at the Trump Organization as a security guard and rose through the ranks to become the director of security. He grew close to Trump during a stint serving as his personal bodyguard and was eventually promoted to chief operating officer.
“I love the guy,” Calamari once told Bloomberg News of Trump. “My thing is, I’ve always promised I would, knock on wood, never let anything happen to him.”
As a longtime loyalist, Calamari likely would have little incentive to cooperate unless he were facing charges. It’s not clear that the district attorney’s office is prepared to bring charges against either Calamari. Both were under investigation prior to the indictments earlier this month, CNN reported.
Though the district attorney’s office has long sought Weisselberg’s assistance, he told prosecutors prior to the indictment that he wouldn’t cooperate, and his stance doesn’t appear to have shifted since being charged.
In addition to the alleged tax scheme, prosecutors have been investigating whether the Trump Organization misled lenders, insurers and tax authorities about the value of certain properties, the treatment of tax deductions and the accounting practices connected to hush money payments that former Trump attorney Michael Cohen made to silence claims of an affair with Trump.
In his 2018 testimony before Congress, Cohen, who pleaded guilty to tax charges and campaign finance crimes in connection with the hush money payments, identified Calamari as one of three people at the Trump Organization who knew that — according to Cohen — Trump provided inflated assets to an insurance company.
Cohen has met with the Manhattan district attorney’s office at least eight times in the course of its investigation.
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