Piles of paper piled up on his desk. Framed magazine covers and memorabilia line the walls. One of Shaquille O’Neal’s giant sneakers is on display along with football helmets, boxing belts and other sports memorabilia, filling the Trump Tower office and limited table space. Long before he entered politics, former US President Donald Trump had a penchant for collecting. And that lifelong habit — combined with his reckless disregard for government record-keeping rules, careless handling of classified information and a chaotic transition born of his refusal to accept defeat in 2020 — have all culminated in a federal investigation that poses extraordinary legal and political challenges. The search of Trump’s Mar-a-Lago club earlier this month to retrieve documents from his White House years was an unprecedented law enforcement action against a former president widely expected to run again. Officials did not disclose exactly what the boxes contained, but the FBI said it recovered 11 sets of classified files, including some designated “sensitive information compartments,” a special category meant to protect secrets that could cause “extremely serious” damage to US interests if publicly revealed. Why Trump refused to hand over the seized documents despite repeated requests remains unclear. But Trump’s violation of the Presidential Records Act, which outlines how the materials are preserved, has been well-documented throughout his tenure. He regularly tore up official documents that later had to be taped up. Official items that traditionally would have been turned over to the National Archives were mixed in with his personal belongings at the White House residence. Classified information was tweeted, shared with reporters and opponents — even found in a White House bathroom compound. John Bolton, who served as Trump’s third national security adviser, said that, before he arrived, he had heard “there was a concern in the air about how he was handling information. And as my time went on, I could certainly understand why.” Others in the Trump administration took more care with sensitive documents. Asked directly if he kept classified information while leaving office, former Vice President Mike Pence told The Associated Press on Friday, “No, I don’t know.” The investigation into Trump’s handling of documents comes as he faces heightened legal scrutiny on multiple fronts. A Georgia investigation into election meddling has edged closer to the former president, with former New York Mayor Rudy Giuliani, a leading defender, informed earlier this month that he is the target of a criminal investigation. Meanwhile, Trump invoked his Fifth Amendment protection against self-incrimination as he testified under oath in the New York attorney general’s long-running political investigation into his business dealings. A top executive of the company pleaded guilty last week to a tax fraud case brought by the Manhattan district attorney. But few legal threats have galvanized Trump and his staunchest supporters like the Mar-a-Lago quest. The former president and his allies have argued that the move amounts to a political prosecution, noting that the judge who approved the warrant has given money to Democrats. The judge, however, has also sided with Republicans. And White House officials have repeatedly said they had no prior knowledge of plans to search the estate. Trump’s allies have tried to argue that the presidency gave him unlimited power to unilaterally declassify documents without a formal declaration. But David Laufman, the former head of the Justice Department’s counterintelligence division, said it doesn’t work that way. “It just seems to me like a post hoc public affairs strategy that has nothing to do with how classified information is actually declassified,” said Laufman, who oversaw the investigation into Hillary Clinton’s personal email server while in office as foreign minister. While he said it is true that there is no statute or provision outlining the procedures the president must follow to declassify information, “at the same time it is ludicrous to assume that a decision to declassify documents would not have been recorded in writing at the same time.” “It’s not self-executing,” he added. “There has to be some objective, contemporary, evidence-based corroboration of the claims they’re making. And of course there won’t be because they’re making it all up.” The decision to keep documents secret at Mar-a-Lago — a property frequented by paying members, their guests and anyone attending the weddings, political fundraisers, charity dinners and other events held on the grounds — was part of a long-standing pattern of contempt for national security secrets. Former aides described a “cavalier” attitude toward classified information playing out in public view. There was the dinner with then-Japanese Prime Minister Shinzo Abe on the Mar-a-Lago patio, where colleagues watched and snapped cellphone photos as the two men discussed details of a North Korean missile test. It was the moment Trump revealed to Russian officials top-secret information purported to have come from Israeli sources about Islamic State militants. And it was when he tweeted a high-resolution satellite image of an apparent explosion at an Iranian space center that intelligence officials had warned was highly sensitive. Trump insisted he had “the absolute right” to share it. Former White House press secretary Stephanie Grisham said Trump was “careless” with sensitive and classified information and “never seemed to engage with why this was bad.” Grisham recalled an incident involving Conan, a US military dog ​​hailed as a hero for his role in the raid that killed Islamic State leader Abu Bakr al-Baghdadi. He said that prior to the dog’s arrival at the White House, staff had been briefed that the dog could not be photographed because the images could endanger its handlers. But when the dog arrived, Trump decided he wanted to show it off to the press. “Because he wanted publicity, Conan left,” he said. “It’s an example of him not caring if he was endangering lives… It was like his own shiny toy that he shows off to his friends to impress them.” Bolton said that, during his time working for Trump, he and others often tried to explain the stakes and risks of revealing sources and methods. “I don’t think any of that sunk in. He didn’t seem to appreciate how sensitive it was, how dangerous it was for some of our people and the dangers they could be exposed to,” he said. “What looks like an innocuous image to a private individual can be a gold mine for a foreign intelligence entity.” “I would say over and over, ‘That’s too sensitive, too sensitive’. And he’d say, ‘I know,’ and then go do it anyway.” Bolton said top intelligence officials would gather before the briefings to discuss how best to handle sensitive matters, strategizing how much to share. Scientists quickly learned that Trump often tried to hang on to sensitive documents and would take steps to ensure the documents were not missing, including using an iPad to show them to him. “Sometimes he’d ask to hold it and they’d say, ‘It’s too sensitive.’ At some point he just wouldn’t give it back.” Trump’s refusal to accept his election defeat also contributed to the chaos that engulfed his final days in office. The General Services Administration was slow to recognize President Joe Biden’s victory, delaying the transition process and leaving little time to prepare. While other White House staff members and even the former first lady began making arrangements, Trump largely refused. At the same time, White House staff were leaving in droves as part of the regular “disembarking process”, morale among others having plummeted following the January 6 attack on the US Capitol. Bolton said he doubted Trump had obtained the documents for nefarious reasons and instead thought Trump likely viewed them as “souvenirs” like the many he had collected over the course of his life. “I think he just thought some things were cool and he wanted them,” Bolton said. “Some days he liked to collect french fries. Some days he liked to collect documents. He just collected things.” The Washington Post first reported in February that the National Archives had recovered 15 boxes of documents and other items from Mar-a-Lago that should have been turned over to the agency when Trump left the White House. An initial review of that material concluded that Trump had brought presidential records and several other documents marked classified to Mar-a-Lago. The investigation into the handling of classified material intensified in the spring as prosecutors and federal agents interviewed several people who worked in the Trump White House about how records — and particularly classified documents — were handled during the chaotic end of the Trump presidency. . a person familiar with the matter told The Associated Press. At the same time, prosecutors also subpoenaed records Trump kept at Mar-a-Lago and subpoenaed surveillance video from Mar-a-Lago that showed the area where the records were kept, the person said. A top Justice Department official traveled to Mar-a-Lago in early June and examined some of the material stored in boxes. After that meeting, prosecutors interviewed another witness, who told them there were likely additional classified documents still stored at Mar-a-Lago, the person said. The person was not authorized to discuss the matter publicly and spoke on condition of anonymity. The Justice Department later sought a search warrant and recovered the additional installments of the classified…