Trump's Legal Outlook Continues to Look Grim. The Matthew Calamari Edition

By Bess Levin, Vanity Fair

23 June 21

The ex-president’s bodyguard turned COO is reportedly being investigated by the Manhattan District Attorney, too.

s part of its criminal investigation into Donald Trump, the Manhattan district attorney’s office has, for many months now, been trying to get Trump Organization CFO Allen Weisselberg, who knows where all the bodies are buried and could likely put the dots together for a jury, to flip. Thus far, it doesn‘t appear as if he’s done so, but the fact that Weisselberg could reportedly face charges this summer presumably ups the chances he’ll cooperate to save himself. In the meantime, though, Cyrus Vance Jr.’s office is apparently looking into another figure who may have some extremely helpful information to share.

The Wall Street Journal reports that New York prosecutors are investigating Matthew Calamari, Trump’s bodyguard turned chief operating officer, and the question of whether or not he was the recipient of “tax-free fringe benefits,” as part of their probe into the company possibly giving out such perks to employees as a way to avoid paying taxes. Calamari has reportedly lived for years in an apartment at the Trump Park Avenue building on the East Side and driven a Mercedes leased through the Trump Organization. His son, Matthew Calamari Jr., also lives in a company-owned building (Junior joined the family business in 2011 right after graduating high school and was named corporate director of security in 2017, according to a LinkedIn profile.) While neither Calamari has been accused of wrongdoing, prosecutors recently advised both men to hire lawyers, sources told the Journal, which is generally not a great sign.

Receiving benefits—such as free apartments, subsidized rent or car leases—from an employer, and not paying taxes on such benefits, can be a crime, although experts said prosecutors rarely bring cases on such perks alone…. Such a recommendation is often a sign that prosecutors’ interest in a subject is intensifying, but doesn’t mean the Calamaris will be charged with wrongdoing.

In 2019 testimony before the House Oversight Committee, former longtime Trump lawyer Michael Cohen mentioned the elder Mr. Calamari as among employees who could attest to what Mr. Cohen described as Mr. Trump’s practice of inflating his assets to insurance companies. The elder Mr. Calamari has worked at the Trump Organization for nearly four decades. He began working for Mr. Trump as his bodyguard after he tackled hecklers at a 1981 U.S. Open women’s semifinal, Mr. Calamari told Bloomberg in 2015. He said Ivana Trump, Mr. Trump’s wife at the time, asked for his name on her husband’s behalf. Mr. Calamari was ultimately promoted to chief operating officer.

In his 2004 book, Trump: How to Get Rich, Mr. Trump wrote, “After getting to know Matthew, I realized he had a lot more to offer than his job title warranted.” He described both Mr. Calamari and Mr. Weisselberg, among others, as “home-run, grand-slam people” in the acknowledgments section.

Weisselberg has not been accused of wrongdoing. Last month, The Washington Post reported that Vance’s office had assembled a grand jury that had already begun hearing evidence, a development that suggests the probe had “reached an advanced stage” after more than two years, and that charges against the ex-president could be coming.