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Jacob ShamsianWed, March 17, 2021, 2:47 PM

matthew calamari
Matthew Calamari in Trump Tower. Drew Angerer/Getty Images
  • Matthew Calamari has worked for Donald Trump for 40 years and is the COO of the Trump Organization.
  • He and his son reportedly oversee the vast surveillance operations on company properties.
  • Michael Cohen alleged he has knowledge of a tax scheme under scrutiny from prosecutors.
  • Visit Insider’s homepage for more stories.

As investigations swirl into Donald Trump and his company’s finances, Matthew Calamari has stayed out of the limelight.

Matthew Calamari
Matthew Calamari, COO of The Trump Organization, attends the Eric Trump Foundation’s 6th Annual Golf Invitational Benefiting The St. Jude Children’s Research Hospital at Trump National Golf Club Westchester on September 10, 2012 in Briarcliff Manor, New York. Bobby Bank/Getty Images

Calamari has worked for Trump for 40 years. His name first pricked up reporters’ ears when Michael Cohen mentioned him in testimony to Congress in 2019. The former Trump Organization executive said Calamari was familiar with Trump’s alleged practice of providing an inflated accounting of his assets to insurance companies are part of a scheme to evade taxes.

As investigators continue to look into Trump’s finances, Calamari’s knowledge of those alleged plans could become increasingly important. The Manhattan District Attorney’s Office is already trying to “flip” Trump Organization CFO Allen Weisselberg, the The Washington Post reported.

If Calamari has any knowledge of Trump’s finances, it’s possible that prosecutors would look into him, as well.

Trump hired him as a bodyguard after seeing him tackle a heckler.

matthew calamari golf
Calamari playing gold at the Trump National Golf Club Westchester in 2012. Bobby Bank/Getty Images

Calamari initially didn’t want to go into security services. As a student at the New York Institute of Technology in Old Westbury, he was a linebacker on the football team. He had dreams of playing football professionally, he told Bloomberg News in 2015.

A knee injury put an end to that and Calamari found himself working in security. At the 1981 US Open, a pair of hecklers interrupted the game between Chris Evert and Martina Navratilova. He decisively handled it.

“I took one guy immediately right down,” he told Bloomberg. Then he tackled another heckler: “I ran right at him, I picked him up, I slammed him to the ground, I carried him down.”

Trump and his wife at the time, Ivana, were impressed, he told Bloomberg. Trump hired him as a personal bodyguard, and he’s risen the ranks ever since, a hardcore Trump loyalist.

“I love the guy,” Calamari told Bloomberg. “My thing is, I’ve always promised I would, knock on wood, never let anything happen to him.”

Now Calamari is the Chief Operating Officer of Trump’s business empire, according to his LinkedIn profile. In his role, he oversees building management, construction, and insurance, he told Bloomberg.

“He promotes you until you fail,” he said. “There are no boundaries.”

He and his son reportedly ran Trump’s surveillance operations.

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Matthew Calamari has worked for Trump since 1981. Drew Angerer/Getty Images

At his properties, Trump runs extensive surveillance far beyond the security operations of normal golf clubs and hotels, according to BuzzFeed News. At his Mar-a-Lago estate, he reportedly had a switchboard that allowed him to eavesdrop on calls made from any room’s telephone.

For years, Calamari ran the company’s surveillance programs at Trump Organization properties, according to BuzzFeed News.

In 2011, his son, Matthew Calamari Jr. joined the Trump Organization. He became the company’s “Director of Surveillance” in May 2016, according to his LinkedIn profile. In April 2017, he was promoted to become the company’s Director of Security. Sources who worked for the Trump Organization told BuzzFeed News that Calamari, Jr. picked up the surveillance gig from his father.

Calamari Jr. attended Chaminade High School, according to his LinkedIn profile. It’s a prestigious Catholic prep school also attended by Newsmax CEO Christopher Ruddy, a close friend of Trump, as well as disgraced former Fox News pundit Bill O’Reilly and Rep. Thomas Suozzi, a Democrat. He then went to Molloy College, graduating with a business degree in 2015.

Both Calamaris are registered Republicans, according to voting records reviewed by Insider, and live in Glen Head, which is part of Suozzi’s district on Long Island.

Calamari didn’t donate to Trump’s presidential runs.

matthew calamari donald trump jr
Donald Trump Jr. and Matthew F. Calamari at Trump National Golf Club Westchester on September 10, 2012 in Briarcliff Manor, New York. Bobby Bank/Getty Images

Calamari didn’t donate to any of Trump’s presidential campaigns, according to FEC records published by the Center for Responsive Politics. He did, however, donate to the late Arizona Sen. John McCain’s campaign in 2008, and to a Democratic-leaning political action committee in 2006.

He also gave $1,000 to former Illinois Rep. Dan Rostenkowski in 1994, just like his colleague Trump Organization CFO Allen Weisselberg did. The donation came just before Rostenkowski, a Democrat leading the powerful House Ways and Means Committee, was criminally indicted for his role in a corruption scandal. The scandal ultimately led to his resignation from Congress and a guilty plea on mail fraud charges.

In addition to his home on Long Island, Calamari has since 2020 owned an apartment in the Trump Parc East, according to real estate records reviewed by Insider. The Manhattan condominium building is also a subject of scrutiny in the Manhattan District Attorney investigation into Trump’s finances.

Calamari is also owed money by Exxon Mobil, according to the New York State Comptroller website.

He had a memorable moment on the “The Apprentice”.

matthew calamari the apprentice
Matthew Calamari stammering through an appearance on “The Apprentice.” NBC

Calamari was in three episodes of “The Apprentice,” Trump’s reality TV show on NBC, according to IMDb. A clip from the second season’s live finale went viral in 2019, after Cohen mentioned Calamari in his hearing.

In the clip, Trump asks Calamari to decide which contestant he likes better. As Trump pressed him to explain his choice, Calamari seemed paralyzed.

“Donald you know I don’t care for Jen very much, gotta be honest with ya,” he said. “Um, because. Wow. Because, uh. Wow, I’m not doing too good, huh? … I like Kelly. Because, wow, OK.”

He turned into a meme.

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Get it? Like the squid dish? Deb Lindsey for The Washington Post via Getty Images

Calamari’s formidable mustache and name — at once evoking seafood and mob connections — turned him into a meme as Cohen mentioned his name during his Congressional testimony.

Cohen implicated Calamari in his testimony to Congress.

michael cohen congress testimony
Michael Cohen, President Donald Trump’s former longtime personal attorney, testified before the House Oversight Committee on Wednesday. Matt McClain/The Washington Post via Getty Images

Calamari’s name came up in Cohen’s testimony through a line of questioning from Rep. Alexandria Ocasio-Cortez of New York.

Ocasio-Cortez asked Cohen whether Trump ever provided inflated assets to an insurance company. Doing so may have allowed him to evade federal and local taxes.

Cohen said that Trump did indeed provide inaccurate asset records. When asked who else would have known about them, he named CFO “Allen Weisselberg, Ron Lieberman, and Matthew Calamari,” all of whom are top executives at the Trump Organization.

Weisselberg was granted immunity to testify in front of a federal grand jury while federal prosecutors investigated Cohen in 2018, but was not a cooperating witness in the federal probes involving Cohen, the Trump Organization, and Trump himself.

Lieberman is the company’s executive vice president of management & development and Weisselberg is its chief financial officer. He continues to work for the Trump Organization as its Executive Vice President of Management and Development, according to his LinkedIn profile.

https://www.yahoo.com/news/know-matthew-calamari-trump-employee-214730376.html

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