Trump's ex-bodyguard Matthew Calamari has lawyered up, on New York prosecutors' advice


New York prosecutors investigating former President Donald Trump's business have advised Trump's former bodyguard and current chief operating officer, Matthew Calamari, and his son that they should get their own lawyers, not use the Trump Organization's attorneys, The Wall Street Journal reports, citing people familiar with the matter. Prosecutors are reportedly looking into whether the Calamaris have illegally avoided paying taxes on benefits provided by the Trump Organization, including housing and cars.
New York City District Attorney Cyrus Vance Jr. has been investigating the Trump Organization for a few years, focused most recently on whether the company manipulates the value of its properties to get loans and lower its taxes. Vance's prosecutors are similarly investigating, and widely believed to be trying to gain the cooperation of, Trump Organization chief financial officer Allen Weisselberg, but they don't appear to have had much luck yet. Now it appears their interest in these benefits extends beyond Weisselberg, the Journal reports, noting that neither Calamari or Weisselberg have been accused of wrongdoing.
The Calamaris have taken the prosecutors' advice and hired Nicholas Gravante Jr., who has represented former AIG head Maurice "Hank" Greenberg and Hunter Biden, among other prominent clients, the Journal reports.
The Week
Escape your echo chamber. Get the facts behind the news, plus analysis from multiple perspectives.

Sign up for The Week's Free Newsletters
From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.
From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.
The senior Calamari has worked for the Trump Organization for decades, starting as Trump's bodyguard in 1981. He is believed to know the details of the company's alleged property value inflation and under-reporting. His son, Matthew Calamari Jr., joined the Trump Organization's security team in 2011, the same year he graduated from high school, and was named corporate director of security in 2017.
The Calamaris live in different luxury Trump apartment buildings on Central Park, the Journal reports. Barry Weisselberg, Allen Weiselberg's son and another Trump Organization employee, lived in the same building as Matthew Calamari Jr., he said in a 2018 deposition for his divorce, testifying that "it was a corporate apartment, so we didn't have rent."
"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," the Journal reports, "although experts said prosecutors rarely bring cases on such perks alone."
A free daily email with the biggest news stories of the day – and the best features from TheWeek.com
Peter has worked as a news and culture writer and editor at The Week since the site's launch in 2008. He covers politics, world affairs, religion and cultural currents. His journalism career began as a copy editor at a financial newswire and has included editorial positions at The New York Times Magazine, Facts on File, and Oregon State University.
-
Home Depots are the new epicenters of ICE raids
In the Spotlight The chain has not provided many comments on the ongoing raids
-
Why does Trump keep interfering in the NYC mayoral race?
Today's Big Question The president has seemingly taken an outsized interest in his hometown elections, but are his efforts to block Zohran Mamdani about political expediency or something deeper?
-
The pros and cons of banning cellphones in classrooms
Pros and cons The devices could be major distractions
-
Why does Trump keep interfering in the NYC mayoral race?
Today's Big Question The president has seemingly taken an outsized interest in his hometown elections, but are his efforts to block Zohran Mamdani about political expediency or something deeper?
-
Judge lets Cook stay at Fed while appealing ouster
Speed Read Trump had attempted to fire Cook over allegations of mortgage fraud
-
House posts lewd Epstein note attributed to Trump
Speed Read The estate of Jeffrey Epstein turned over the infamous 2003 birthday note from President Donald Trump
-
Supreme Court allows 'roving' race-tied ICE raids
Speed Read The court paused a federal judge's order barring agents from detaining suspected undocumented immigrants in LA based on race
-
Trump threatens critics with federal charges
Feature Days after FBI agents raided John Bolton's home, Trump threatened legal action against Chris Christie
-
South Korea to fetch workers detained in Georgia raid
Speed Read More than 300 South Korean workers detained in an immigration raid at a Hyundai plant will be released
-
Why are Trump's health rumors about more than just presidential fitness?
TODAY'S BIG QUESTION Extended absences and unexplained bruises have raised concerns about both his well-being and his administration's transparency
-
'The McDonald's menu board is one fascinating thing'
Instant Opinion Opinion, comment and editorials of the day