Everything you need to know about Matthew Calamari, Trump's employee of nearly 40 years who went viral after being implicated in Michael Cohen's blockbuster testimony

Drew Angerer/Getty ImagesMatthew Calamari in Trump Tower.
  • Matthew Calamari knew about a fraudulent insurance scheme that would help President Donald Trump evade taxes, according to Michael Cohen’s testimony to Congress Wednesday.
  • Calamari isn’t famous, but he plays an important role at the Trump Organisation as its COO.
  • He first began working for Trump as a bodyguard in 1981, after Trump saw him tackle a heckler at the US Open.
  • Calamari and his son reportedly oversee the Trump Organisation’s vast surveillance operations on the company’s properties.
  • He had a memorable moment in the second season of “The Apprentice,” where he appeared to freeze up on camera.
  • His name also briefly became a meme.

In Michael Cohen’s public testimony Wednesday, he implicated a member of President Donald Trump’s orbit who has largely escaped scrutiny: Matthew Calamari.

Calamari, Trump’s former personal lawyer said, 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 the House of Representatives continues to look into Trump’s secretive finances, his knowledge of those alleged plans could become increasingly important.

Calamari’s name instantly pricked reporters’ ears and his name turned him into a minor meme.

Here’s everything you need to know about him.

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

Bobby Bank/Getty ImagesCalamari playing gold at the Trump National Golf Club Westchester in 2012.

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 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

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

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 Organisation properties, according to BuzzFeed News.

In 2011, his son, Matthew Calamari, Jr., joined the Trump Organisation. He became the company’s “Director of Surveillance” in May 2016, according to his LinkedIn profile. In April 2017, he was promoted as the company’s Director of Security. Sources who worked for the Trump Organisation 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 US 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.

He had a memorable moment on the “The Apprentice”

NBCMatthew Calamari stammering through an appearance on ‘The Apprentice.’

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 Wednesday, 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 paralysed.


“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

Geoff Peters/FlickrGet it? Like the squid dish?

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

Cohen implicated Calamari in his testimony to Congress

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

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 “Allen Weisselberg, Ron Lieberman, and Matthew Calamari,” all of whom are top executives at the Trump Organisation.

While Calamari is the company’s COO, Lieberman is the company’s executive vice president of management & development and Weisselberg is its chief financial officer.

Weisselberg was granted immunity to testify in front of a federal grand jury while federal prosecutors investigated Cohen in 2018,according to the Wall Street Journal. But he is not a cooperating witness in the federal probes involving Cohen, the Trump Organisation, and Trump himself, according to NBC News.

Calamari didn’t immediately respond to INSIDER’s request for comment.

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