August 31, 2022 2:36 PM EDT

When FBI agents descended on Donald Trump’s Florida home in Mar-a-Lago this month, they opened a desk drawer in his personal office and found classified documents mixed with the former President’s personal effects. The find flew in the face of months of assurances from Trump’s legal team that he had turned over all the secret records he had taken from the White House and that any other government records he had were in a storage room at the club. While federal officials already suspected that Trump’s lawyers had misled them, the contents of that desk drawer shifted the spotlight squarely to Trump himself.

The revelation was among multiple detailed allegations included in a filing unsealed in court late Tuesday. Prosecutors said that there was evidence that “efforts were likely taken to obstruct the government’s investigation” and that government records were “likely concealed and removed” from the storage room where they had been kept.

The court filing ratcheted up the stakes of the investigation into Trump’s hoarding of materials from his time as President, a baffling saga that has left even some of his strongest supporters confused about the motivations behind his actions. While the specific reasons Trump held on to these documents remains unclear, life-long personality traits are likely what brought Trump to this moment. He’s an inveterate pack rat. His desk at Trump Tower in New York and his private dining room off the Oval Office were often stacked with papers and mementos. And he loved to show off. With visitors in front of him, he would casually rummage through his piles for letters, photographs, and magazine covers as a way to highlight his connections, fame and power. And he has long prided himself on being defiant, and seems to draw strength from being seen as pushing back against those in his way. He sidestepped an indictment for obstructing the Mueller investigation and held onto the Republican votes in the Senate to beat two impeachment trials.

But his current fight with the National Archives over a trove of documents may turn out to be the legal quicksand Trump has the hardest time escaping. His lawyer, his custodian of records, and Trump himself could all be criminally liable for obstructing an investigation to recover national security secrets he allegedly took with him from the White House to Mar-a-Lago when he left office 19 months ago.

Just two months before the August Mar-a-Lago search, during a June 3 visit to the club by federal prosecutors, Trump’s lawyer gave investigators a thick, rust-colored folder, double-wrapped in tape—an apparent precaution to protect the state secrets inside. Investigators saw it as an acknowledgment that not all of the classified documents in Trump’s possession had been returned in January, when 15 boxes had been sent to the National Archives.

But that wasn’t all. Trump’s team made assurances to the federal officials that the issue had been resolved. Trump’s lawyer told investigators that day that “all available boxes were searched” and “there were no other records stored in any private office space or other location,” according to an investigator’s account of interactions with Trump’s legal team that was part of the document filed in court late Tuesday. When investigators looked inside the taped accordion file, they were alarmed to find 38 classified documents inside, including 16 documents marked “secret” and 17 marked “top secret.” Trump’s lawyer “offered no explanation” for why there were still government records at Mar-a-Lago five months after Trump had handed over 15 boxes of government records to the National Archives.

That same day, on June 3, a person who identified themselves as Trump’s custodian of records (the name has been blacked out) swore in a legal certification in response to a court ordered grand jury subpoena that there had been a “diligent search” of the boxes from the White House and all relevant documents with classified markings were handed over. Two months later, the FBI’s search, executed with a court-approved warrant, revealed that wasn’t true. Agents removed 33 boxes of material, which included more than 100 classified records, some of which contained information that was so secret, the federal investigators themselves had to get additional security clearances to examine them.

An evidence photo taken by FBI agents during the August search and released Tuesday shows more than a dozen pages marked “secret” and “top secret” and boldly colored classified cover sheets splayed out over filigree carpet. In the image, next to the classified papers, is an open Bankers Box holding a gold-framed cover of TIME depicting Trump in the Oval Office.

This is all unfolding in the realm of legal subpoenas, court filings and sworn statements, where lies and misrepresentations to a court can prompt harsh legal penalties. When prosecutors requested the search warrant for Mar-a-Lago, they presented evidence in court that there was probable cause to believe crimes had been committed, including “willful retention of national defense information,” “concealment or removal of government records” and “obstruction of a federal investigation.”

In their latest filing, prosecutors appeared to go a step further, asserting that they believe they have evidence of a crime. “The government also developed evidence that government records were likely concealed and removed from the Storage Room and that efforts were likely taken to obstruct the government’s investigation,” says the Justice Department’s Aug. 30 court filing.

The latest government filing is the most damning so far, and only came about in response to a request from Trump’s legal team for a judge to appoint a so-called “special master” to review the material seized from Trump’s club in August and set aside anything covered by attorney-client privilege or executive privilege. Prosecutors have said that since the FBI is part of the executive branch and the records are not Trump’s records but belong to the government, executive privilege would not apply. In addition, Justice Department officials notified the judge that a so-called taint team of investigators not involved in the case already reviewed the information taken from Mar-a-Lago and set aside some material that could be considered outside the scope of the investigation.

When Trump himself was President, he signed a law beefing up the penalties for mishandling classified material—increasing the crime for inappropriately moving classified material from a misdemeanor to a felony, and the maximum penalty from one year to five years in prison. The importance of protecting classified information was an issue he campaigned on, routinely criticizing his opponent Hillary Clinton for using a private server for emails while she was Secretary of State. “In my administration, I’m going to enforce all laws concerning the protection of classified information. No one will be above the law,” Trump said at a campaign event in Charlotte, N.C., on Aug. 18, 2016.

Trump has repeatedly confirmed in his public statements that he had government records at Mar-a-Lago. He’s maintained, without evidence, that he declassified the documents he had in his possession. He’s also said, falsely, that he was cooperating with federal officials to return the documents. In Trump’s response on social media Wednesday to the most recent court filings, he didn’t dispute he had the documents and wasn’t returning them. “Terrible the way the FBI, during the Raid of Mar-a-Lago, threw documents haphazardly all over the floor (perhaps pretending it was me that did it!), and then started taking pictures of them for the public to see. Thought they wanted them kept Secret? Lucky I Declassified!” Trump wrote. A former Trump administration official, Kash Patel, has said that Trump declassified the documents he took from the White House. But, so far, there is no public record of those steps being taken.

Even if some of the documents were formally declassified before Trump left office on Jan. 20, 2021, prosecutors have pointed out that such records are still not Trump’s to own; they belong to the government. And his hoarding of them, as well as misleading federal investigators about them, could still constitute a violation of federal laws.

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