“Yes, sir, Mr. Trump,” Calamari replied.
Moments later, Trump upped the ante: “Would you kill for me, Matty?”
Calamari’s answer came quickly. “Yes, sir,” he said.
On Wednesday afternoon, social media exploded with mentions of Calamari’s name, and within hours he was trending on Twitter. Calamari had unexpectedly come up during Michael Cohen’s highly anticipated testimony to members of Congress, and the questions abounded, chief among them being: Who?
Contrary to some of the theories posited by social media users who suggested Calamari is, as one person put it, “a made-up name by the screenwriter of a mafia B movie who doesn’t know any actual Italians,” the longtime Trump Organization employee is very real. He was plucked from obscurity by the president nearly 40 years ago, rapidly ascending the ranks at the company to become its executive vice president and chief operating officer, while cementing his status as a member of Trump’s trusted inner circle. The former bodyguard’s meteoric rise, wrote Trump biographer Michael D’Antonio in May 2017, was due in large part to one of his defining qualities — his unwavering loyalty to a man who “sought those who could be trusted to put their boss first.”
"I love the guy,” Calamari told Bloomberg News in 2015, speaking about Trump. “My thing is, I’ve always promised I would, knock on wood, never let anything happen to him.”
Calamari first caught Trump’s attention in 1981, when he was a security guard working at the U.S. Open tennis tournament. Hecklers disrupted a semifinal match between rivals Chris Evert and Martina Navratilova, and Calamari took swift action.
“I took one guy immediately right down,” he told Bloomberg. When another person started to act up, Calamari said, “I ran right at him, I picked him up, I slammed him to the ground, I carried him down.”
Trump witnessed Calamari’s handling of the chaotic situation and was impressed, The Washington Post’s Marc Fisher reported in 2016. Though he hadn’t even met Calamari at the time, Trump, who has been known to fill roles within his business and administration with people who look the part, hired the mustachioed former college linebacker as a bodyguard.
By the early ’90s, Calamari had been promoted to security director for Trump Tower in New York, and his responsibilities within the Trump Organization only continued to expand. In Trump’s 2004 book, “Trump: How to Get Rich,” he explained Calamari’s career trajectory.
“After getting to know Matthew, I realized he had a lot more to offer than his job title warranted, and he has proven me right,” Trump wrote, noting that as executive vice president, Calamari was in charge of building operations and ran the company’s entire security organization. “He’s a dedicated and trustworthy worker, and any CEO in his right mind would want to have him around.”
That same year, Trump’s soft spot for Calamari was put on full display during the live finale of season 2 of “The Apprentice."
The moment occurred when Calamari was prompted to say why he favored one contestant over the other.
“Donald you know I don’t care for Jen very much,” Calamari said in his thick New York accent, speaking into a microphone held by the live finale’s host, Regis Philbin. “Gotta be honest with ya.”
Then, as Calamari attempted to continue his explanation, he appeared to go blank.
“Um, because,” he faltered. “Wow, because uh, wow. I’m not doing too good.”
A surprisingly sympathetic Trump interjected, “You’re doing great, Matt, who do you like?”
“I like Kelly,” Calamari responded quickly, but once again lost his grasp on words when he made an effort to expound on his opinion.
As the audience burst out into raucous laughter, Calamari, clearly flustered, sank down into his seat. The man next to him rubbed his back reassuringly.
“Donald, what he’s trying to say is he likes Kelly,” Philbin said.
“People think this stuff is easy,” Trump responded. “It’s not so easy.”
Aside from his unfortunate network TV appearance, Calamari has largely stayed out of the media limelight until recently.
In October 2016, then-BuzzFeed News reporter Aram Roston published an in-depth story about Trump’s security operation, in which Calamari was described as “daunting and even intimidating.” Others, Roston reported, called him “an efficient and quiet professional.” By then, Calamari’s son, Matthew Calamari Jr., was also working for the company and involved in security, specializing in surveillance, according to BuzzFeed.
A few months later, in February 2017, Calamari was mentioned in a Politico report detailing allegations that Trump’s private security force lacked basic procedures and policies and allowed guards to deal with protesters and journalists in any way they deemed fit. According to Bloomberg, Calamari liked to “watch over his boss on the trail,” but his official role on the campaign was unclear.
In August 2017, BuzzFeed News reported that Calamari had allegedly been part of a group that “terrorized” the family of a Trump Organization employee in 1995. The employee claimed he had proof the company committed “financial improprieties” and other misconduct, BuzzFeed reported, citing a lawsuit. In a statement to BuzzFeed, the Trump Organization denied the claims, calling them “completely inaccurate, ridiculous and utterly false.”
During Wednesday’s hearing, Cohen told Rep. Alexandria Ocasio-Cortez (D-N.Y.) that Trump had previously provided inflated assets to an insurance company. When Ocasio-Cortez pressed Cohen about who else knew the president had done this, Calamari was among the names listed.
Calamari could not be reached for comment early Thursday.
On social media, Calamari’s name, which is likely pronounced “Cala-mary” and not like the squid dish, drew widespread confusion and ridicule.
Soon, people began circulating photos of Calamari, as well as his memorable appearance on “The Apprentice,” finally providing the uninitiated with a face to match the name.