Donald Trump's former BODYGUARD-turned-his-top executive is being investigated in NYC criminal probe amid claims employees illegally 'received tax-free perks such as apartments and car leases'

  • Matthew Calamari and his son Matthew Jr. have hired their own attorneys
  • Prosecutors are looking into whether the Trump Org. illegally gave him perks 
  • Receiving these benefits tax-free is illegal, but criminal cases are rarely pursued 
  • Calamari has worked for Trump for 40 years, first as his bodyguard and now as the Chief Operating Officer 
  • Calamari's son became the corporate director of security in 2017 

New York prosecutors are investigating whether Donald Trump's former bodyguard received tax-free benefits as part of their criminal probe into whether the Trump Organization illegally avoided paying taxes on perks, according to a report Monday.

Matthew Calamari has hired his own attorney as investigators look into whether he received such luxuries as free apartments, subsidized rent or car leases without paying taxes while he was working for the former president, according to the Wall Street Journal.

Calamari, now the Trump Organization COO, and his son Matthew Calamari Jr, the corporate director of security, have not been accused of any wrongdoing. 

Prosecutors in recent weeks, however, advised the father and son that they should hire lawyers, The Journal said.  

The senior Calamari has lived in an apartment at Trump Park Avenue in the Upper East Side for years and drives a Mercedes leased through the Trump Organization, according to the report.

His son lives in Trump Parc East, the same building where longtime CFO Allen Wessielberg's son Barry lived, according to a deposition statement he made in 2018 during his divorce to ex Jennifer. 

Their involvement in the probe is part of a wider investigation into whether the Trump organization overvalued assets - including real estate - in order to get tax and financial benefits.  

New York prosecutors are investigating whether Donald Trump's former bodyguard Matthew Calamari received tax-free benefits as part of their criminal probe into whether the Trump Organization illegally avoided paying taxes on perks

New York prosecutors are investigating whether Donald Trump's former bodyguard Matthew Calamari received tax-free benefits as part of their criminal probe into whether the Trump Organization illegally avoided paying taxes on perks

Trump is pictured with Calamari (right) and NFL center Nick Mangold at Briarcliff Manor in New York on September 13, 2011

Trump is pictured with Calamari (right) and NFL center Nick Mangold at Briarcliff Manor in New York on September 13, 2011 

Former President Donald Trump (center) appears during his Apprentice years alongside Matthew Calamari (left) Apprentice judge Carolyn Kepcher (right)

Former President Donald Trump (center) appears during his Apprentice years alongside Matthew Calamari (left) Apprentice judge Carolyn Kepcher (right) 

Matthew Calamari swings a golf club at the Eric Trump Foundation's 6th Annual Golf Invitational Benefiting The St. Jude Children's Research Hospital at the ex-president's Bedminster resort in 2012

Matthew Calamari swings a golf club at the Eric Trump Foundation's 6th Annual Golf Invitational Benefiting The St. Jude Children's Research Hospital at the ex-president's Bedminster resort in 2012

Receiving such benefits can be a crime, but cases are rarely brought, but it shows that Manhattan District Attorney Cyrus Vance Jr,'s office is looking into whether the Trump Organization provided benefits to more staff beyond Weisselberg. 

The former president has denied any wrongdoing and says the investigations by Vance and New York Attorney General Letitia James are further examples of 'witch hunts' by Democrats.

The Calamaris hired Nicholas Gravante Jr., who heads commercial litigation at Cadwalader, Wickersham & Taft LLP, The Journal said. In the past, Gravante has represented Hunter Biden, the president's son, and James Biden, the president's brother. 

In 2019, Michael Cohen said in his testimony to the House Oversight Committee that Calamari Sr. could allegedly back claims that Trump had inflated prices of his assets to insurance companies. 

He pointed a finger at Weisselberg, Calamari and Ron Lieberman, an executive vice president at the Trump Organization, describing the trio as 'top executives at the Trump Organization.'  

Trump hired Calamari in 1981 when he saw him tackle hecklers at the US Open that year. 

'I took one guys immediately right down,' Calamari 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.' 

At the time Trump was married to first wife Ivana, and they were impressed, the now ex-president told Bloomberg.  

'I love the guy,' Calamari said of Trump. 'My thing is, I've always promised I would, knock on wood, never let anything happen to him.'    

In the former president's 2004 book Trump: How to Get Rich, he wrote: 'After getting to know Matthew, I realized he had a lot more to offer than his job title warranted.'

Calamari told Bloomberg News in 2015 that he didn't want to get into the security industry and instead wanted be a professional football linebacker. 

But he suffered a knee injury that ended his career early. 

'He promotes you until you fail,' Calamari said. 'There are no boundaries.'

Buzzfeed News reported that Calamari was in charge of Trump's surveillance operations at his golf clubs and hotels.   

Calamari Jr. joined the Trump Organization in 2017. He graduated high school in 2011.  

The senior Calamari has lived in an apartment at Trump Park Avenue in the Upper East Side for years and drives a Mercedes leased through the Trump Organization, according to the report. Miss South Carolina Courtney Hope Turner shows off her karate skills with Calamari in 2011

The senior Calamari has lived in an apartment at Trump Park Avenue in the Upper East Side for years and drives a Mercedes leased through the Trump Organization, according to the report. Miss South Carolina Courtney Hope Turner shows off her karate skills with Calamari in 2011 

Calamari (back right) watches on during Trump's wedding to Marla Maples in 1993

Calamari (back right) watches on during Trump's wedding to Marla Maples in 1993 

Calamari, now the Trump Organization COO, and his son Matthew Calamari Jr, the corporate director of security, have not been accused of any wrongdoing. He is pictured with Don Jr in 2017

Calamari, now the Trump Organization COO, and his son Matthew Calamari Jr, the corporate director of security, have not been accused of any wrongdoing. He is pictured with Don Jr in 2017 

Who's who in New York criminal probes into Trump: His longtime CFO, the 'quiet money man' and two Democrat AGs

New York state has opened a criminal investigation into former US president Donald Trump (pictured November 2020)

New York state has opened a criminal investigation into former US president Donald Trump (pictured November 2020)

A Democratic prosecutor nearing the end of his term, a loyal lieutenant of the Trump family and a lawyer determined to sink his former boss: AFP details some of the players in New York's criminal probe into Donald Trump.

Cyrus Vance

The 66-year-old Democrat has been Manhattan District Attorney since 2010. He was the first to launch a criminal investigation into the Republican ex-president.

Manhattan District Attorney Cyrus Vance (pictured May 2020) has doggedly pursued Donald Trump, winning a years-long battle to obtain his tax records and deploying significant human and financial resources to the politically sensitive investigation

Manhattan District Attorney Cyrus Vance (pictured May 2020) has doggedly pursued Donald Trump, winning a years-long battle to obtain his tax records and deploying significant human and financial resources to the politically sensitive investigation

Vance, whose father was US Secretary of State under President Jimmy Carter, has sometimes been accused of a reluctance to prosecute the rich and powerful.

He delayed filing charges against disgraced producer Harvey Weinstein before securing a landmark conviction last year.

Vance has doggedly pursued Trump, though, first by winning a years-long battle to obtain his tax records and secondly by deploying significant human and financial resources to the politically sensitive investigation.

He has announced that he will not run for a fourth term when his current one expires in December, and many observers expect him to go out with a bang by filing what would be the first indictment against a former US president.

Letitia James

The Democrat became the first Black woman to become New York state attorney general in 2018.

Since then, the 62-year-old has forged a reputation as a combative and independent prosecutor, filing countless civil actions against large companies, particularly tech giants, and the National Rifle Association (NRA).

In addition to Donald Trump, Letitia James (pictured August 2020) is also investigating New York's governor, Andrew Cuomo, over sexual harassment allegations and his response to the coronavirus pandemic

In addition to Donald Trump, Letitia James (pictured August 2020) is also investigating New York's governor, Andrew Cuomo, over sexual harassment allegations and his response to the coronavirus pandemic

When Trump was in the White House, James launched dozens of civil actions against his government.

She is also investigating New York's powerful Democratic governor, Andrew Cuomo, over sexual harassment allegations and his response to the coronavirus pandemic.

James has been cited as a possible successor to Cuomo, particularly if her investigation forces him to resign.

Allen Weisselberg: Trump Organization CFO

The 73-year-old is the Trump Organization's long-serving chief financial officer and one of the family's most loyal servants.

He began as an accountant for Trump's father's company before joining the Trump Organization as financial controller in the 1980s when Donald established himself as a Manhattan real estate mogul.

Allen Weisselberg, pictured standing behind former president Donald Trump and his son Donald Jr. in January 2017, has served as the chief financial officer of the Trump Organization since the 1980s

Allen Weisselberg, pictured standing behind former president Donald Trump and his son Donald Jr. in January 2017, has served as the chief financial officer of the Trump Organization since the 1980s

Weisselberg has been around for all of Trump's entrepreneurial adventures, including when his Atlantic City casinos went bust.

According to Barbara Res, a former executive vice president at the Trump Organization, Weisselberg 'thought Trump was a god,' she told the Daily News.

Investigators believe Weisselberg knows all of the Trump family secrets and have been putting pressure on him for months to cooperate with their investigation.

Observers are closely watching whether Weisselberg will turn against his former boss. 

Jennifer Weisselberg: Ex-daughter in law of Allen Weisselberg

Earlier this year, investigators from the Manhattan District Attorney's office were seen carrying boxes of documents and laptops from Weisselberg's Manhattan apartment. 

She was married ton Allen Weisselberg's son Barry from 2004 to 2018.

In an interview with DailyMail.com in June, she said the former president is a 'sweet' and 'generous' man who helped pay for her children's private schooling out of kindness and good-will, rather than to dodge taxes. 

If there was any unlawful activity within the Trump Organization it would be thanks to her former in-laws who still work for the company, she told DailyMail.com in an exclusive interview.

Up until 2018, the mother-of-two was married to Barry Weisselberg, who manages Trump's Central Park ice rinks, and her father-in-law was Allen Weisselberg, who became the chief financial officer when Trump became president.  

'Allen orchestrated the finances, and Donald is just sort of naïve,' Jennifer said.

'It's provable that his trusted CFO is putting [Trump] and his children in a bad legal position.' 

 She is also set to testify to the grand jury.

Earlier this year, investigators from the Manhattan District Attorney's office were seen carrying boxes of documents and laptops from Weisselberg's Manhattan apartment. She was married ton Allen Weisselberg's son Barry (right) from 2004 to 2018

Earlier this year, investigators from the Manhattan District Attorney's office were seen carrying boxes of documents and laptops from Weisselberg's Manhattan apartment. She was married ton Allen Weisselberg's son Barry (right) from 2004 to 2018

Jeff McConney: Trump Organization Senior Vice President

McConney was known as the man in the Trump Organization who would hand over key documents to Trump and CFO Allen Weisselberg before meetings and would be responsible for cutting checks for big payments.

He was the first high-profile member of Trump's business empire known to have testified in front of the New York Grand Jury deciding whether to indict Trump.

Trump's fixer Michael Cohen told The Daily Beast:  'Think of The Trump Organization as a small, one-teller bank.

'Donald [Trump] would be the president. Allen [Weisselberg] would be the branch manager. Jeff [McConney] would be the teller. Every single transaction was booked through McConney. 

Concerns for prosecutors is that McConney is seen as a Trump loyalist and, as The Daily Beast reported, someone who hates left-wing politics. 

Michael Cohen

Trump's ex-personal lawyer was sentenced to three years in prison in 2018 for tax evasion and violating campaign finance laws relating to Trump's 2016 vote win.

Cohen was one of Trump's closest henchmen for a decade, once proudly boasting that he was prepared to 'take a bullet' for the real estate mogul-turned-president.

Michael Cohen, pictured March 2021, openly rejoices in former boss Donald Trump's legal troubles on Twitter and through his podcast

Michael Cohen, pictured March 2021, openly rejoices in former boss Donald Trump's legal troubles on Twitter and through his podcast

He turned against his former boss, though, deciding to collaborate with federal investigators in Manhattan.

During a Congressional hearing in February 2019, Cohen alleged -- among other things -- that Trump regularly undervalued or overvalued his assets, both with banks and insurance companies.

Cohen openly rejoices in Trump's legal troubles on Twitter and through his podcast 'Mea Culpa.'

Source: AFP

The comments below have not been moderated.

The views expressed in the contents above are those of our users and do not necessarily reflect the views of MailOnline.

We are no longer accepting comments on this article.