Report: Trump’s Legal Outlook Does Not Appear to Be Improving

Earlier this week, we learned that special counsel Jack Smith—who is investigating Donald Trump’s attempt to overturn the 2020 election and the insurrection that followed—had reportedly taken an extra special interest in Mike Pence’s grand jury testimony on the matter. That’s a turn of events that is unlikely to go over great with the ex-president, but what of Smith’s other criminal investigation into Trump, the one involving his handling of highly classified documents (and possible obstruction)? It appears there’s equally not-great news for the former guy on that front too.

CNN reports that prosecutors working for Smith have “been asking questions in recent weeks about the handling of surveillance footage” at Mar-a-Lago, after the Trump Organization received a federal subpoena for the information last summer. That “handling”—or likely mishandling—of the footage in question has “prompted a new round of grand jury subpoenas to top Trump employees in the last few weeks,” according to sources familiar with the matter who spoke to CNN. Those employees are said to include Matthew Calamari Sr., the chief operating officer of the Trump’s family business, and his son, Matthew Calamari Jr., the director of security for the company. (If Calamari Senior sounds familiar, it’s because he has worked for the Trump Organization for decades, after being hired by Trump in the 1980s because the real estate developer was impressed by how Calamari tackled a heckler at the US Open.) Both Calamaris are expected to testify before a grand jury on Thursday, where they will likely be asked “about the handling of the surveillance footage and Trump employees’ conversations following the subpoena,” sources familiar with the matter told CNN.

An attorney for Calamari Sr. did not respond to CNN’s request for comment; an attorney for Calamari Jr. declined to comment.

Last year, prosecutors obtained footage showing Walt Nauta, a longtime valet of Trump‘s, moving boxes at Mar-a-Lago after the government had issued a May subpoena demanding the return of all classified documents. (All the documents were not returned, hence the raid on Mar-a-Lago in August.) When initially questions by the FBI, Nauta denied having any knowledge of any classified documents at the Palm Beach resort; later he told investigators, per The Washington Post, “that he had moved boxes at Trump’s direction after prosecutors sent a subpoena seeking the return of all documents marked classified and kept at Mar-a-Lago.”)

Last month, shortly before he was charged with 34 class E felonies by the Manhattan district attorney’s office, the Post reported that the Justice Department and FBI had “amassed fresh evidence pointing to possible obstruction by former president Donald Trump in the investigation into top secret documents found at his Mar-a-Lago home.” According to the outlet, investigators had “gathered new and significant evidence that after the subpoena was delivered, Trump looked through the contents of some of the boxes of documents in his home, apparently out of a desire to keep certain things in his possession.” In addition, people working on the probe were said to have found evidence suggesting that Trump told people to mislead government officials in early 2022, when the National Archives was working with the DOJ to recover the documents Trump had taken with him when he left the White House, which—and we’re no lawyers—seems like a big no-no. Also, prosecutors reportedly learned that the former guy “ignored requests from multiple advisers to return the documents to the archives…that he asked advisers and lawyers to release false statements claiming he had returned all documents, and that he grew angry after being subpoenaed for the documents.”

And somehow, that was not all! According to the Post, investigators also found evidence that Trump “sought advice from other lawyers and advisers on how he could keep documents after being told by some on his team that he could not,” and that “multiple advisers warned Trump that trying to keep the documents could be legally perilous.” Again, doesn‘t seem great!

Earlier this year, a judge ordered Trump attorney Evan Corcoran to appear before the grand jury investigating the documents case, which Corcoran had previously tried to get out of by invoking attorney-client privilege. As The New York Times reported in October, it was Corcoran who asked fellow Trump lawyer Christina Bobb—after Trump received the subpoena for the documents—to “sign a statement” saying that “the Trump legal team had conducted a ‘diligent search’ of Mar-a-Lago and found only a few files that had not been returned to the government.” That statement, as the August raid showed, obviously turned out not to be true. (Trump has denied any wrongdoing in the documents case.)