Pop culture obsessives writing for the pop culture obsessed.

Trump associate Matthew Calamari is both real and a doofus

Photo: Drew Angerer (Getty Images)

Former Trump lawyer Michael Cohen didn’t drop jaws during his congressional testimony yesterday, but he did float the name Matthew Calamari, and, for that, we thank him. When Cohen made mention of Calamari—saying he was one of a few men who knows that President Trump provided inflated assets to insurance companies—people patently refused to believe such a man could exist. Such a name, any logical human would argue, is just too on-the-nose for the kind of two-bit cronyism going on in the Trump Organization.


But, as many soon discovered, Matthew Calamari is somehow not the creation of a Sopranos Name Generator. He is, in fact, a real person. What’s more, he looks, sounds, and acts exactly how you would imagine a Matthew Calamari would. Here is a clip of him from the live season two finale of The Apprentice, in which he cringingly struggles to formulate a sentence about why he’d prefer one contestant over the other.


To be fair, it doesn’t seem like Calamari was being employed for his massive intellect. According to The Washington Post, Trump hired the hulking Calamari as a bodyguard in the early ‘80s after witnessing him tackle two hecklers at the 1981 U.S. Open tennis tournament. Over the years, Calamari moved his way up the Trump Organization ladder, first becoming security director for Trump Tower in New York and, in a massive leap, executive vice president of the entire business operation. He’s been cited in numerous Trump biographies for his fierce loyalty to the president and even once admitted his willingness to kill for the man. So, yeah, not a genius.


The exact role Calamari played in Trump’s alleged illegal activities remains to be seen. We’re looking forward, though, to seeing him one day spill the beans on Tony Bologna, Vinny Mortadella, and Pasta Ravioli.


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About the author

Dan Neilan

Contributor, The A.V. Club. Have Fun — Will Travel.