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Donald Trump’s Classified Documents Scandal Is Back

Donald Trump speaking at the 2015 Conservative Political Action Conference (CPAC) in National Harbor, Maryland. Image Credit: Gage Skidmore.
Donald Trump speaking at the 2015 Conservative Political Action Conference (CPAC) in National Harbor, Maryland.

Special counsel Jack Smith is looking at Mar-a-Lago footage: Matt Calamari, a Donald Trump staffer, and his son recently testified as the special counsel closes in on a possible charging decision in the case of the classified documents. 

Donald Trump Has a New Legal Issue

Remember Matthew Calamari?

He was one of the more obscure of the hanger-on of the Donald Trump era, best known for his very funny name, his impressive mustache, and the circumstances of his arrival in Trump’s orbit. Trump met Calamari in 1981 at the U.S. Open tennis tournament when, working security, he threw some hecklers out of the venue. Trump later hired him, and he rose over the ensuing decades to become chief operating officer of the Trump Organization. 

Calamari has only been minimally involved with most scandals and legal cases involving Trump over the years, and while the New York Times reported in 2021, that New York prosecutors were “weighing charges” against him in the Trump Organization probe, they ultimately did not, although the company was convicted of tax fraud last December. 

But Calamari was back in the news this week, when both Calamari and his son, Matthew Calamari Jr., were scheduled to appear before the grand jury investigation in Washington that is investigating the classified documents at former President Trump’s home. The younger Calamari is the Trump Organization’s director of security. 

The Calamaris, CNN reported, are part of a “new round of grand jury subpoenas” that have resulted from the office of Special Counsel Jack Smith looking into Mar-a-Lago surveillance footage in the case. The two Calamari men were to be asked about “the handling of the surveillance footage and Trump employees’ conversations following the subpoena,” CNN reported. 

Dozens of Mar-a-Lago employees, from top Donald Trump staffers to servers, were subpoenaed in March

The same network had earlier reported that surveillance footage had captured Walt Nauta, a Trump aide, and another employee moving boxes out of a storage closet at the former president’s estate in Florida. 

Per a Politico report late last month, some of the documents marked classified that were found at Mar-a-Lago were “memos written for former President Donald Trump’s calls with foreign leaders,” according to a letter by Trump’s lawyers. 

In the same letter, Trump’s attorneys argued that the Justice Department should not be running any investigations of classified documents held by political figures, whether it’s Trump, President Biden, or former Vice President Mike Pence. 

“Please know that despite the differences in the cases, we do not believe that any of these three matters should be handled by DOJ as a criminal case,” the attorneys said in the April letter. “Rather, the stakeholders to these matters should set aside political differences and work together to remediate this issue and help to enhance our national security in the process.”

Vanity Fair wrote this week that following the news of the Calamaris’ testimony, Trump’s overall legal outlook does “not appear to be improving.” He’s already indicted in New York in the Stormy Daniels case, and facing a possible judgment in a civil case accusing him of rape and defamation, in a case that he has no-showed. That’s to say nothing of the special counsel probes. 

More Problems for Donald Trump Coming Soon? 

And CNN legal analyst Elliot Williams said this week on television that it’s “quite clear” that prospectors are looking into possible obstruction of justice on the part of Donald Trump. 

“I think there’s two buckets of crimes possibly being investigated here, the actual mishandling or possession of documents in violation of law, but also obstruction of justice after the fact,” Williams said, per a transcript published Thursday by Mediaite. “And I think what they will be trying to get at today is, number one, any conversations leading up to any moving or mishandling of surveillance footage, but also conversations afterward, as Paula had noted. All of those could go to this question of whether someone tried to falsify or conceal a record as a means of getting in the way of an investigation.”

Expertise and Experience:

Stephen Silver is a Senior Editor for 19FortyFive. He is an award-winning journalist, essayist and film critic, who is also a contributor to the Philadelphia Inquirer, the Jewish Telegraphic Agency, Broad Street Review and Splice Today. The co-founder of the Philadelphia Film Critics Circle, Stephen lives in suburban Philadelphia with his wife and two sons. Follow him on Twitter at @StephenSilver.

Written By

Stephen Silver is a journalist, essayist, and film critic, who is also a contributor to Philly Voice, Philadelphia Weekly, the Jewish Telegraphic Agency, Living Life Fearless, Backstage magazine, Broad Street Review, and Splice Today. The co-founder of the Philadelphia Film Critics Circle, Stephen lives in suburban Philadelphia with his wife and two sons. Follow him on Twitter at @StephenSilver.

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