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The inside story of how Trump transplanted the chaos and norm flouting of his White House into his post-presidential life, leading to a criminal investigation into his handling of classified documents that presents potential legal peril
The Nov. 22 dinner, described by three people familiar with the event, neatly encapsulates Trump’s post-presidential life — a reminder of how a former president who worked steadily to dismantle the government guardrails imposed by his elected office is now almost entirely without restraint.
From almost the instant it became clear he had lost the 2020 election, Trump refused to accept the results, creating a disorganized transition process during which he rebuffed efforts to prepare for his post-presidency.
In the two years since he left office, Trump has re-created the conditions of his own freewheeling White House — with all of its chaos, norm flouting and catering to his ego — with little regard for the law. With this behavior, Trump prompted a criminal investigation into his post-presidential handling of classified documents to compound the ongoing one into his and his allies’ efforts to overturn the 2020 election results — which presents potential legal peril and risks hobbling his nascent bid to be elected president again in 2024.
Even as he works to convince supporters that the documents probe is the result of an overblown paperwork dispute, and that the FBI’s Aug. 8 search of his Mar-a-Lago Club was an abuse of power, the investigation is in fact a product of how Trump has approached post–presidential life.
Though few rules guide the life of a former president, Trump has exhibited a characteristic disinterest in following any of them. These days, he is served almost exclusively by sycophants, having replaced successive rounds of loyal yet inexperienced aides with staffers even more beholden and novice.
Natalie Harp, one of Trump’s employees and a former host on the pro-Trump cable network One America News, often accompanies Trump on his daily golf outings, riding the course in a golf cart equipped with a laptop and sometimes a printer to show him uplifting news articles, online posts or other materials.
On some quiet days, another aide, Molly Michael, who served as Trump’s assistant in the White House, has called around to Trump’s network of allies across the country requesting that they dial the former president to boost his spirits with positive affirmations. There’s nothing going on, she has told them, adding that his friends know how restless he gets when nothing is going on, according to people who have heard her appeal.
Multiple Trump advisers said there is no senior aide living in Florida full time, with advisers flying in and out as needed. “He needs someone there to say, ‘Here’s a really bad idea, and this is why.’ I don’t think he has that kind of crowd around him right now. Nor does the president want anybody like that,” said David Urban, a longtime Trump adviser turned critic.
Like he did as president, Trump has looked for ways to turn a profit with his new arrangement: Trump’s staff tried, unsuccessfully, to get the General Services Administration to pay rent at Mar-a-Lago — potentially for his lifetime — for the office space he has created for himself above the club’s ballroom.
A longtime Trump confidant termed his Mar-a-Lago existence, where he has tried to re-create the trappings of the presidency, as “sad.” Comparing it to life at the White House, this person added, “It’s like a Barbie Dream House miniature.”
This behind-the-scenes account of Trump’s post-presidential life is based on interviews with 23 people, some of whom spoke on the condition of anonymity to disclose private details about Trump and his orbit, many of which have not been previously reported.
Trump spokesman Steven Cheung responded to questions about this reporting with a statement that said Trump “spent the last two years continuing to build up the MAGA movement and helping elect America First candidates across the country, to the tune of a 98.6% endorsement record in primary elections.”
“There is nobody who has worked harder to advance the conservative movement. After years of biased media coverage and Big Tech meddling in an election to help Joe Biden and the Democrats, President Trump continues to be the single, most dominant force in politics and people— especially unnamed sources who purport to be close to him— should never doubt his ability to win in a decisive and commanding fashion,” he added.
Observers and some Trump allies alike believe that after years of investigations into Trump’s conduct, it is his behavior since leaving office that may be most likely to lead to his criminal indictment — for mishandling classified documents and obstructing the work of federal investigators hunting for those records.
“I think it’s pretty obvious, when there was no around to tell you that, ‘No, Mr. President, you cannot do that,’ it just leads inevitably to this kind of problem,” said Chris Whipple, author of “The Gatekeepers,” a history of White House chiefs of staff.
“In a way it looks almost like the Trump Presidency 2.0,” he said. “Just no guard rails, on steroids.”
‘Opportunities for messing up’
Trump is hardly the first ex-president to struggle with life as a private citizen after the heady experience of holding the world’s most powerful job. Bill Clinton, for instance, filled hours in his first months after leaving office holed up at home in Chappaqua, N.Y., bingeing TV shows and movies he had missed as president on a TiVo gifted to him by the Hollywood director Steven Spielberg.
Most former presidents have compensated for the boredom by throwing themselves into the task of crafting a new kind of public life, pursuing charitable goals and managing their legacies through books and the building of a presidential library.
But not Trump. Unwilling to accept the reality of his November 2020 election loss to President Biden, Trump resisted efforts to plan for his post-presidential life, according to people close to him. The result was a delayed, chaotic and little-thought-out process that many around Trump believe set the stage for troubles to come.
In his final weeks in office, White House staffers interested in working for Trump after he stepped down were required to engage in a strange dance in which they competed for post-presidential jobs without admitting there would be no second Trump term — a concession that risked angering the outgoing president and thereby eliminating them from consideration. It was all “cloak and daggers,” said one person familiar with the dynamic.
By law, presidents and vice presidents leaving office are together provided up to $2.6 million in public funds to “wind down” their offices, pay staff salaries, rent office space and buy supplies like copy paper and pens. Once requested, the money can be accessed for 30 days prior to leaving office and up to six months after.
Documents released by GSA show that Trump’s White House chief of staff Mark Meadows did not sign a formal agreement requesting the money until Jan. 11, five days after the attack on the U.S. Capitol and several weeks after funding would have otherwise been available by law.
The delay impacted aides to Vice President Mike Pence, too, who could only then begin to tap the funds and start looking for office space to locate transition offices. Over the frantic days that followed, they selected the 12th floor of a generic-looking office tower managed by the GSA in Crystal City, near Ronald Reagan Washington National Airport in Northern Virginia. Not long after, Trump aides contacted Pence’s team, according to a person familiar with the discussions. Though many around Pence believed Trump had endangered the life of his vice president during the Jan. 6, 2021, attack, now Trump’s team asked: Could they use the Crystal City space for transition offices as well?
While Meadows signed the GSA document, the work of transitioning Trump to life in Florida actually fell to lower level staffers — including operations aide William “Beau” Harrison, body man Nick Luna and his personal assistant Michael — who held less sway with the outgoing president and knew less about government functions, people familiar with the transition said. Harrison, Luna and Michael declined to comment about their roles in the transition.
All administration documents, which represent the public historical record of a president’s time in office, are required by law to be sent to the National Archives and Records Administration at the end of the term for safekeeping. Gifts given to the president are also supposed to go to the Archives no later than Inauguration Day, unless the president pays the government an amount equivalent to the item’s appraised value.
Archives officials had been working with a military team since December 2020 to pack up and ship documents and gifts from the White House offices to storage in Maryland, with trucks going back and forth on a nearly daily basis until Trump left office on Jan. 20, 2021. But as his remaining days ticked down, they became concerned about boxes of documents that Trump had taken back to the White House residence. Meanwhile, a Jan. 11 email from Harrison to GSA officials shows he anticipated as many as 100 boxes of presidential gifts would be stored at the Crystal City office after Trump left the White House.
People around Trump said they believe the chaotic transition played a key role in Trump’s ability to carry off thousands of government documents to his Florida club. It also meant that the Crystal City office was crammed with leftover stuff from the Trump White House with no apparent organization and little knowledge of what was even there.
The emails were released by the GSA on the agency’s website in response to a public records request from Bloomberg News. They track a chaotic effort to move the leftovers of Trump’s concluded term to Florida and frequent confusion over what was owned by the American people and what was owned by Trump.
In April 2021, a Trump aide emailed a GSA official to ask if the agency’s transition funds could be used to ship an enormous portrait of Trump to Florida. The painting, she explained, weighed 300 pounds and measured 6 by 8 feet in its crate.
“I am so sorry to ask — this is a weird one!” wrote Trump aide Desiree Thompson Sayle. After several days, the GSA official responded that the agency’s lawyers had nixed the request. “Since this is personal property, GSA Transition funds cannot be used for this shipping,” GSA official Kathy Geisler responded. In July, Sayle followed up to explain the team’s resolution for the painting, which was apparently given to Trump after the presidency ended: “We are loading the large portrait received after the 21st on a Penske truck to transport to my house so I can put it on my moving van.” Neither Sayle nor Geisler responded to requests for comment.
Max Stier, the president of the Partnership for Public Service, which assists with transitions, said the process for winding down a presidency can be challenging. But, he added, “it’s a lot harder if you start from the proposition that [the trappings of office] belong to you, than if you start with the proposition that it belongs to the office and to the country.”
“In a complicated process, if you don’t have the right underlying ethos, the opportunities for messing up are much larger,” he said.
As July 2021 drew to a close and Trump staff were losing access to transition funds, the emails show they raced to close down the Crystal City office and ship the remaining items to Florida, where Trump had now established his primary base of operations at Mar-a-Lago in Palm Beach. He was now a Floridian, having changed his voter registration from New York to Florida. Emails show GSA officials rented an 8-by-10-foot storage unit in July 2021 for the former president at a private facility in nearby West Palm Beach and then arranged to ship more than 3,000 pounds of boxes from Virginia to the unit, as well as another nearly 1,500 pounds of boxes to Mar-a-Lago in September.
The documents show one employee who was listed as a contact for the shipment to the storage unit was Kitty Gubello, a longtime employee of Mar-a-Lago — an example of how thoroughly Trump intermingled his public and private lives. (Asked for comment, Gubello wrote in a text message: “My allegiance is to the club and the family. You will get nothing out of me.”)
Lawyers for Trump found two items with classification markings during a recent search of the storage unit, The Washington Post has reported. The discovery meant the items had likely followed a circuitous path since Trump left office, moving from the White House to Crystal City to the West Palm Beach unit, spending nearly two years in facilities that lacked security features required for the storage of classified materials.
One person familiar the Virginia office called it “not especially secure” — the 12th floor of a high rise, where people came and went. Meanwhile, the storage facility, located off a busy interstate in West Palm Beach, lacks visible security guards near the rear entrance. People come and go there as well. Inside are hundreds of numbered storage units with locked metal garage doors. Representatives of the facility did not respond to a request to comment about security measures.
Trump advisers who helped oversee moving the boxes to Mar-a-Lago and the storage facility said there was no cataloguing system or organizational structure to track what ended up where — and the storage room was initially packed.
After transition funding lapses, former presidents are still by law afforded some financial support for the remainder of their lives, including funding for “suitable office space,” as determined by the GSA.
For Trump’s personal use, his young aides spent months redecorating office space located above the 20,000 square foot ballroom at his Florida club. The former president personally directed the process, choosing the furniture, rugs and paintings, and designating which mementos of his time in office would be displayed. Even so, people familiar with the process said aides fretted he would deem the redesigned space insufficient after four years in the Oval Office.
At some point, his aides requested that GSA formally lease the space from Mar-a-Lago for his use as a post-presidential office — an arrangement that would have directed a stream of taxpayer money back to Trump, potentially for the remainder of his life — a person familiar with the request said. GSA declined, instead leasing office space in West Palm Beach.
A GSA spokesperson said the agency discussed “a variety of lease options” for Trump’s permanent use, “including the possibility of a lease at Mar-a-Lago.” The spokesperson said the conversations were “preliminary,” did not result in a deal and the agency currently pays no money to Trump-owned properties.
‘There are no protocols’
Trump took time to readjust to his post-presidential life. He was surprised by how much his Secret Service detail and motorcade had shrunk. He no longer had use of a major aircraft; Air Force One was unavailable to him, and his company’s TRUMP-emblazoned Boeing 757 was in the shop — repairs that took years, with delays that infuriated him. His living spaces were far smaller than the White House. And he was annoyed that his statements to the press were not getting much attention, four advisers said.
At one point in early 2021, Trump asked a team of advisers if he could summon a press pool — like the contingent of reporters, photographers and videographers who travel with the president — for an event at his Florida club. But there was no pool on call because he was no longer president.
“We had to explain to him that he didn’t have a group standing around waiting for him anymore,” one former aide said.
Instead, they gathered the few reporters who happened to be reporting in Palm Beach, two people familiar with the matter said.
He was routinely angry, advisers said, about being removed from social media, particularly his beloved Twitter, where his account was suspended two days after Jan. 6, 2021, for risking further violence with his false tweets. His mood was foul for months, as he paid attention to little else than the lost election, conspiracy theories to explain away the Jan. 6 attack and mounting legal bills from a rotating cast of attorneys he spoke to daily.
“It was a really dark, dark time,” the aide said, recalling that staff would ask “are you going to set up a library? What’s your post-presidential foundation?”
“He wasn’t interested in any of that at all,” the aide added.
People who know Trump said the need for attention that has been a driving force throughout his life has not dwindled since he left the office that shone on him the world’s brightest spotlight. That has pushed him to seek adulation from a court of supplicants who pay for access to Trump at his Mar-a-Lago and Bedminster, N.J., clubs, where he has spent most of his time.
“The appetite for attention hasn’t waned, but that’s where he gets it now,” a Trump confidant said. “The networks don’t carry his rallies. He doesn’t get interviews anymore. He can’t stand under the wing of Air Force One and gaggle [with reporters] for an hour.”
Trump rarely agrees to interviews these days with independent journalists that could become confrontational; several advisers noted he recently granted an interview with NewsNation’s Markie Martin, the sister of his longtime press aide, Margo Martin.
On a typical day since leaving office, advisers said, Trump gets up early, makes phone calls, watches television and reads some newspapers. Then, six days a week, he plays 18 or sometimes 27 holes of golf at one of his courses. After lunch, he changes into a suit from his golf shirt and slacks and shows up in the office above the Mar-a-Lago ballroom or, when he is in New Jersey, a similar office in a cottage near the Bedminster club’s pool.
By evening, Trump emerges for dinner, surrounded most nights by adoring club members who stand and applaud at his appearance; they stand and applaud again after he finishes his meal and retires for the night. He often orders special meals from the kitchen and spends time curating the music wafting over the crowd, frequently pushing for the volume to be raised or lowered based on his mood. In the Oval Office, Trump had a button he could push to summon an aide to bring him a Diet Coke or snacks. Now, he just yells out commands to whichever employee is in earshot.
At times, Trump makes unannounced visits at weddings, gala benefits and other events being hosted by paying customers in Mar-a-Lago’s ballroom, basking as attendees mob him for selfies. He has also attended fundraisers there; many Republican candidates have paid Trump to use his club as a venue at which to raise campaign funds.
“There are no protocols. He plays golf. He meets with people in the afternoon. He really doesn’t do a lot of consequence most days,” one person in his orbit said.
At times, advisers said, he becomes absorbed in his role as the de facto leader of the Republican Party, bringing about $150 million into his main fundraising vehicle and doling out endorsements to reward supporters and punish critics. At others, he appears aimless and rooted in the past, obsessing about an election two years ago and petty slights.
Harp, who has worked for Trump since the spring, offered a different view, writing in an email that the former president is “constantly busy and working.”
“In fact, I can’t believe how much work he is able to get done,” she wrote.
As a private citizen, Trump is far more isolated than he was as president. He makes virtually no public appearances outside of political rallies where he is surrounded by even larger crowds of screaming fans. (Despite declaring his reelection campaign in the Mar-a-Lago ballroom on Nov. 15, he has not emerged from his cocoon for a rally out in the country since then.) He takes no vacations to properties he does not own. He almost never encounters people willing to challenge his behavior — much less true political opponents.
Several people close to Trump said there are only a few people who are willing to deliver bad news left in his orbit, political adviser Susan Wiles chief among them. His circle has shrunken considerably, with many of his longtime allies attempting to avoid dinner invites — and some even weighing roles with other 2024 candidates.
“No one wants to confront him because he can be a beast,” one adviser said. After the dinner with Fuentes and West, who now goes by the name Ye, advisers to Trump were flooded with calls from allies, lawmakers and others questioning the decision and urging him to apologize. Trump received few of them himself, however, people familiar with the matter said.
Some longtime aides are particularly distressed by the influence of Harp, 31, who is rarely absent from his side. She is said to cater attentively to his need for constant praise. While other advisers have urged Trump to vet his statements to the social media platform Truth Social, Harp has been willing to post whatever Trump wants without review. She often perches herself right outside his office, two advisers said, and follows Trump around all day, including on the golf course.
“She is indicative of the people around him who just love him,” the adviser said. “Love him too much.”
“Like other staffers, I do spend time with him,” Harp wrote, adding that she has “a great respect” for Trump.
“He is extremely popular with the people,” she wrote. “I see that by being with him.”
Cheung, the Trump spokesman, defended Harp: “Among many other talented members of the team, Natalie is dedicated and loyal and has been invaluable.”
Michael, 30, was also known for her loyalty — both in the White House, where she served as an assistant posted immediately outside the Oval Office, and at Mar-a-Lago in the post-presidency. She had a reputation in the White House for always being ready with the answer Trump wanted or the piece of paper he needed. “She just understands how Trump wanted things,” said one former colleague.
Michael left Trump’s employ late this summer, after being questioned by investigators about how Trump handled documents.
One of the only aides who worked for Trump in the White House and still spends significant time in his presence is Nauta, people close to Trump said. A native of Guam, Nauta enlisted in the U.S. Navy in 2001 and was promoted from the White House mess to serve as the president’s valet not long after Trump took office. In that role, he spent all day in and out of the Oval Office, bringing the president glasses of Diet Coke, fetching his coat and moving documents from room to room — duties not unlike those he performs for Trump now that he is out of office. In Trump’s world, where rivalries are common, Nauta is widely liked and perceived as a genuinely nice guy.
Prosecutors have been seeking to secure cooperation from Nauta in the investigation of classified documents stored at Mar-a-Lago, people familiar with the case have said. When first questioned by the FBI, they said he denied any knowledge or awareness of sensitive documents at Mar-a-Lago. When questioned a second time, however, he told investigators he moved boxes at Trump’s direction after a grand jury subpoena in May was delivered demanding the return of any documents with classified markings. Nauta is one of several potentially key witnesses whose lawyers’ fees are being paid through Trump’s political action committee, Save America. Some experts have said the arrangement could influence Nauta’s testimony.
Even when Trump was president, former White House chief of staff John F. Kelly said senior staff dreaded the time the president spent at the 17-acre club in Palm Beach because he would often return to Washington brimming with off-the-wall ideas planted by Mar-a-Lago members.
“So many of the members knew exactly how to get what they wanted from him. It was all about his vanity,” Kelly said. “It was never good when he was there for long periods of time.”
Now that he is away from the security of the White House, people close to Trump say more random figures around the country have his personal cellphone number and can easily get access to him, particularly if they play to his obsession with false theories that the 2020 election was stolen. As a confidant put it, “Some guy from Arizona is calling and saying, ‘You won’t believe the fraud we saw.’”
Since the November dinner with Ye and Fuentes, advisers have attempted to install a bit more structure, trying to keep a top aide with him at all times and saying they plan to hire more Florida-based staff next year for the campaign. But one former aide said recent events show how security and political protocols have fallen away from Trump, starting in the White House and accelerating in the two years since.
“At first it was: how did Omarosa get in here?” said the former aide said, referring to the former reality show star who caused a stir when she briefly was able to secure a White House job early in Trump’s tenure.
“Then it was: What is Sidney Powell doing here?” the former aide said, describing the moment in December 2020 when a group including the lawyer was able to talk their way into an Oval Office meeting with Trump to discuss overturning the election.
“Now it is: What was Nick Fuentes doing having dinner with Trump?” the former aide concluded.
‘What happened to the rest of the boxes?’
The May 2021 email from a top official at the National Archives did not initially set off alarm bells for Trump’s team. In the email, the official flagged that some high-profile documents from Trump’s time in office appeared to be missing from the records his team had turned over as he was leaving the White House. “It is absolutely necessary that we obtain and account for all presidential records,” the Archives official wrote.
But for months, Trump resisted the Archives’ request that he return the documents, informing staffers that boxes at Mar-a-Lago contained only news clippings, golf clothes, gifts and nonsensitive documents. What’s more, he argued that anything from his time as president was his to keep. Told by one aide in October 2021 that Archives officials had made a determination that missing records belonged to the American people and needed to be returned to the government, Trump responded, “It’s a bunch of crap,” according to one of his advisers.
Trump agreed to return some of the boxes only after the Archives threatened to notify Congress or the Justice Department. Trump packed the boxes himself, Michael told others. Those offering to help were warned by one of Trump’s lawyers, Alex Cannon, that doing so could put them in jeopardy, the adviser said.
Finally in December 2021, Trump aides informed the Archives that some notable documents had been located, including correspondence with North Korean leader Kim Jong Un that Trump had once touted as “love letters.”
The following month, Trump returned 15 boxes to the National Archives. Some of his aides were immediately worried. They knew there had been more than 15 boxes stashed in a storage room in a basement area beneath the public areas of Mar-a-Lago. “What happened to the rest of the boxes?” one lawyer asked others, according to the Trump adviser.
In February, Trump told his team to release a public statement that all materials had been returned, and inform the Archives of the same. His spokesman and lawyer declined, people familiar with the matter said.
The lawyers working on the case — Cannon, former deputy White House counsel Pat Philbin and others — were soon replaced by a coterie of lawyers who told Trump what he wanted to hear. That group formally included Boris Epshteyn and Evan Corcoran, as well as Tom Fitton of Judicial Watch, who played an informal role. Fitton argued to other lawyers that presidents are allowed to deem their records personal, a claim Trump echoed to his lawyers. Fitton declined to comment on his role.
When Archives officials opened the boxes they received from Florida, they soon discovered that some documents inside had markings indicating they were classified at the highest levels. They contacted the FBI. By May, after interviewing Trump aides, authorities were convinced that additional classified records might still be held at Mar-a-Lago and sent a grand jury subpoena seeking their return.
In June, two Trump lawyers met with Justice Department officials and turned over a taped up folder containing 38 documents with classification markings. One of the lawyers, Christina Bobb, also provided a signed statement saying she had been told boxes sent to Florida from the White House had been diligently searched and no other documents with markings were in Trump’s possession.
But when the FBI returned in August, this time with a court authorized search warrant, they gathered 103 classified documents, and took an additional 13,000 documents after examining a storage area in the byzantine lower levels of the club and Trump’s office and residence at the club.
The Ye dinner just before Thanksgiving reinforced questions that had already been raised about storing highly sensitive material at the club, which hosts regular public events and where some guests and employees are foreign nationals. National security experts and even some former Trump staff have called the club a counterintelligence headache.
In 2019, for instance, a Chinese national was arrested carrying phones and other electronic devices after getting past a reception area by saying she was headed to the pool. People who have visited the club since Trump left office have said security is even more lax now, with guests often able to access the property without even showing an identification.
Karen Giorno, the former Trump adviser who brought Ye and Fuentes to the club, has told others that she had forgotten her driver’s license when she arrived for dinner and was able to access the property by showing a security guard a bank card with her name on it.
While Trump continues to receive Secret Service protection as a former president, the detail is there to guard him, not provide broader security to the club. When one aide recommended the club subject visitors to more thorough vetting, Trump replied, “The members need to be able to come and go,” according to someone familiar with the exchange. He has told advisers that security is not a problem since everyone visiting the club loves him.
The club, meanwhile, is bordered by residential streets, including one to the north which ends at a gate with only a small sign to warn away trespassers.
Visited on a day late last month — four months after the club was searched by the FBI, and just as scandal was breaking over how easily Ye’s entourage was able to access the facility — there were no security guards at the entry point to the former president’s home.
Helderman, Dawsey and Parker reported from Washington and Alemany from Palm Beach. Alice Crites and Devlin Barrett in Washington contributed to this report
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