When it finally dawned on Donald Trump in the twilight of his presidency that he wouldn’t be living at the White House for another four years, he had a problem: He had barely packed and had to move out quickly.

West Wing aides and government movers frantically tossed documents and other items into banker boxes that were shipped to a storage room at his Mar-a-Lago club in Florida along with other, previously packed records set aside by Trump, sometimes erratically so, according to two sources with knowledge of Trump’s move and records issues.

There, in that Mar-a-Lago room, some of the boxes contained documents with sensitive materials that the federal government appears to consider so important to national security that FBI agents Monday took the unprecedented step of executing a search warrant at the home of a former president to seize them. The records comprised 11 sets of classified documents, including some that were labeled secret and top secret, according to a property receipt from the search.

Trump’s style of handling White House documents has been described by people who worked for him as slapdash and ad hoc, contributing to the debacle he now faces. He was known to rip up records that aides would have to retrieve from trash cans or from the floor and tape back together, according to former aides and multiple reports.

“It worried people all the time,” John Bolton, one of Trump’s former national security advisers, recalled in an interview.

“Trump had a habit of grabbing intelligence documents,” said Bolton, who has been a sharp critic of the former president. “God knows what he did with it.”

The criminal investigation into how sensitive records moved from the White House to Trump’s beachfront club writes a new chapter of his political biography. It’s a story of his impulsive instincts and disregard for established rules or norms that repeatedly created trouble for him in office and now may jeopardize the 2024 election bid that he could launch at any time.

Three separate criminal investigations swirl around the former president: the records case, the probe concerning his role in the attempt to overturn Joe Biden’s victory in the 2020 election, and his effort to nullify Biden’s victory in Georgia, a crucial swing state.

In the run-up to Congress’ certification of Biden’s victory on Jan. 6, 2021, Trump acted as if he had won the election — he hadn’t — and did little to ensure a smooth transition, according to the source familiar with Trump’s move who spoke on condition of anonymity because of the records investigation.

The source said that it was only after Jan. 6 — two weeks before Biden’s swearing-in — that he began to make serious preparations to vacate the White House. And the process was a mess.

“It was a chaotic exit,” this source said. “Everyone piled everything — staff, the White House movers — into the moving trucks. When they got to Mar-a-Lago, they piled everything there in this storage room, except for things like the first lady’s clothes. Everything in a box went there.”

“He didn’t care. He didn’t care about the boxes. He was in a dark place at the time, if you remember. He didn’t even unpack things,” the source continued. “Over time, the staff moved them back in. If you had brought him into that storeroom, and asked, ‘Which are your presidential papers?’ he couldn’t tell you.”

But Bradley Moss, an attorney who specializes in national security law, said the search warrant executed by the FBI raises a question as to whether Trump knew he had sensitive documents and was keeping them from the federal government.

“Whether he was obstructing or whether it was Trump being Trump is the big unknown,” Moss said.

According to advisers, confidants and former aides, Trump is a “pack rat” who tends to leave the actual packing to underlings. At the end of the day, they clear his desk of paperwork — notes, scribbles, newspaper clippings, printed-out-emails, the new tree alignment for a golf course, a new grill for Mar-a-Lago — and the contents are placed in a box on the floor.

When filled, the box is removed by an aide and stored elsewhere. When he travels, an aide sometimes brings boxes along.

It was no different when he was president: Trump would board Air Force One or his Marine One helicopter, and his body man or valets would be toting boxes packed with briefing papers he’d ripped from binders, random papers that someone might have handed him, press clippings, defense memoranda, daily intelligence briefings or other classified material, according to former White House aides.

“They cover the gamut of everything,” a former White House aide who witnessed the spectacle said, declining to comment on the record because of the federal investigation.

Another former White House aide said that Trump was never much concerned about record management.

“He’d have no awareness,” this person said. “When he was done with a piece of paper, he’d rip it up and throw it on the ground. That was his way of saying he’s done … [but] the narrative [that] he was ripping up documents like he was his own personal shredding machine is not accurate — he’d rip it in half, not usually into a thousand pieces.”

Sometime last year, the National Archives reached out and asked Trump to turn over documents he was supposed to relinquish under the Presidential Records Act, a statute meant to preserve records for posterity, according to the two sources familiar with the chaotic move to Mar-a-Lago and records issues. Trump initially said he had already given over everything, but then he checked and found some records during the 2021 winter holiday and turned them over, the sources said.

But in January 2022, the National Archives insisted that more records were missing, and Trump provided 15 boxes worth. Some, however, contained classified information and the agency then referred the matter to the Justice Department for further investigation, setting up a June meeting that resulted in still more records being turned over to the government.

Trump’s representatives said they believed the matter was closed, and that all documents had been rendered. After the search and the rendering of documents in June, one of Trump’s lawyers signed a document indicating Trump had no more “responsive” records — records that fit the scope of what was requested — according to The New York Times, which cited four sources with knowledge of the document. NBC News has not independently seen or confirmed the document.

But the FBI collected subsequent information that indicated there were more sensitive documents, leading it to get a warrant to search Mar-a-Lago Monday.

At least two dozen FBI agents executed the search warrant and carted off more boxes and records, according to the search warrant’s property receipt. The Justice Department and the FBI declined to comment for this article. In an unusual public statement Thursday, Attorney General Merrick Garland called for the unsealing of the search warrant and property receipt and said federal law and department rules prevented him from providing further details as to the basis of the search.

Trump spokesperson Taylor Budowich said Trump had “great care” for the handling of presidential records and blamed the General Services Administration, which manages and supports the basic functioning of federal agencies, for a haphazard move.

“President Trump has great care for the importance of presidential records and presidential record keeping, so much so that both himself and his representatives have spent nearly two years painstakingly working with appropriate entities to ensure any items improperly moved by the General Services Administration were appropriately returned,” Budowich said in a written statement.

The GSA said in a written statement that “the responsibility for making decisions about what materials are moved rests entirely with the outgoing president and their supporting staff.”

Budowich noted that Trump gave documents willingly before and said that, in June, “DOJ and FBI officials were welcomed into Mar-a-Lago, provided with a tour, and given additional documents that had been requested.”

Indeed, in a show of hospitality, Trump offered the officials a Coke before they began their search in June, according to a source familiar with that meeting.

When Trump first took office, his administration had a loose system for controlling the flow of paper to and from the president, according to former White House officials who spoke on condition of anonymity, citing the federal investigation. He was getting documents that didn’t go through the national security process or any other.

When John Kelly became White House chief of staff in the summer of 2017, he said he would remind Trump about the importance of abiding by the Presidential Records Act. A newcomer to public office who was accustomed to running his business his own way, Trump chafed under the regimen, Kelly said.

“When I got there,” said Kelly, a retired four-star Marine Corps general, the staff secretary was “taking stuff out of the trash cans and taping it back together. That continued while I was there.”

A former senior White House aide who was there at the time told NBC News that internal procedures tightened for a bit, but there was invariably slippage.

“We had something approximating a process,” this person said, speaking on condition of anonymity because of the ongoing criminal investigation. “He’s a total pack rat, keeps all sorts of stuff.”

Trump could be cavalier about material, crumpling up his papers or tearing them into pieces and leaving them on the floor, the former aide said.

Trump also saved sentimental items, advisers said. He would ask to keep items that were fun to show off: classified surveillance photos or letters from foreign leaders, like France’s Emmanuel Macron, Canada’s Justin Trudeau and North Korea’s Kim Jong Un, they said.

Trump seemed especially fond of his correspondence from Kim. Bolton, in an interview, mentioned a letter that Trump had gotten from the North Korean leader and said that “John Kelly took it from him and we put it back in the right place.” (Kelly confirmed the account). “We gave Trump a copy of it back. He had a habit of taking stuff and you’d never see it again.” (Some of the documents contained in the 15 boxes retrieved in January included correspondence from Kim, according to The Washington Post, citing two people familiar with the contents.)

At the height of the 2020 campaign, Trump was also keenly interested in all of the records relating to the government’s investigation into Russia’s interference in the 2016 election. He sent out a tweet ordering all such documents immediately declassified.

But when media organizations tried to gain access to the records, White House Chief of Staff Mark Meadows argued in court that the records were not instantly declassified. After he left office, Trump was unaware that the records hadn’t been declassified and angrily swore at Meadows, according to a Trump adviser.

“What the f—, Mark?” Trump screamed on the phone, according to the adviser who heard the exchange.

By the end of his presidency, Trump had come to believe that his word alone could declassify any record in any way he wanted and that he didn’t need to follow standard rules for records management. Many scholars and lawyers disagree, but they are in accord on one point: Following policies and procedures is a best practice for avoiding some of the problems Trump is now facing.

“The reason you create a paper trail is so that people can go back and say, ‘Here’s the document, here’s the memo from the White House counsel. I declassified these documents, specifically laid out on this day when I was president,’” said Charles Stimson, a senior fellow with the conservative Heritage Foundation and a former federal prosecutor.

“It becomes murkier when a president says, ‘I looked at a box and I declassified everything in that box.’ Technically, he can do that,” Stimson said. “But the better course of action is to identify the document, make a contemporaneous memo through the White House counsel, the chief of staff or an aide who has clearance to see those documents and have that declassification memo.”

Trump did none of that for many of the records.

In applying for the search warrant for Mar-a-Lago, the FBI cited three laws concerning federal records that don’t specifically require the documents in question to be classified, which could make it tougher for Trump to raise his defense of presidential declassification powers, according to Moss and other attorneys.

On Thursday, just hours after Garland spoke and said he had personally authorized the Mar-a-Lago search, The Washington Post reported that FBI agents were looking for classified documents related to nuclear weapons, citing people familiar with the investigation. NBC News has not independently verified The Washington Post report, and Trump denied it, though on Friday he inaccurately suggested it wouldn’t be unprecedented for a former president to possess nuclear-related documents.

Still, even critics like Bolton say they’re not sure Trump was that careless.

“We don’t know what Trump has at Mar-a-Lago and people shouldn’t hyperventilate over it until we know more. Just because a piece of paper has the word ‘nuclear’ on it somewhere doesn’t mean it’s apocalyptic if it gets out.”

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