The best advice I’ve ever received came from my mom. “Don’t write anything that you wouldn’t want the whole world to see,” she often said when I was younger. That wisdom served me pretty well throughout the rise of social media, and it often comes in handy in a profession where everything under your byline may be scrutinized by what can be a less-than-forgiving national audience. But I don’t think I’ll ever be anywhere near as good at following that advice as former President Donald Trump apparently is.
Last month, the National Archives recovered 15 boxes of Trump White House records that Trump had apparently absconded with after leaving office just over a year ago. What exactly those boxes contain isn’t fully known—some of the reported contents include a personal letter from his predecessor, Barack Obama, for his first day in office, as well as some of Trump’s “correspondence” with North Korean dictator Kim Jong Un. Based on what it recovered, however, the National Archives reportedly asked the Justice Department to investigate whether he had broken federal laws for mishandling classified information.
The unearthed records come as Trump’s other antipathies toward his paper trail have come into focus. According to The New York Times, the House January 6 committee has found unexplained “gaps” in the White House call records it obtained from the Trump administration files, with some conversations known from other sources not showing up on the official records. And Times reporter Maggie Haberman described, in her upcoming book on Trump, how his proclivity for destroying public records went as far as trying to flush them down White House toilets, leaving staffers to find them backed up and clogged with wads of nonflushable paper.
All of this helps shed some light on why Trump has, thus far, evaded a wide range of consequences throughout his life: a lifelong drive to avoid creating any written records that could be used against him in a court of law. In some ways, Trump isn’t all that shy about writing things down. After all, he spent more than a decade on Twitter before the platform banned him in January 2021 after he incited a mob to attack Congress. There, he seemed to share almost every thought he had. My favorite glimpse into his mind came in the early morning hours of November 12, 2012, when he wrote, “It makes me feel so good to hit ‘sleazebags’ back—much better than seeing a psychiatrist (which I never have!)”
But the promiscuity of his Twitter output is an outlier among his other tech habits. Trump is notorious for not using email; he’s made a practice of routing such correspondence through a secretary or another employee whenever he’s deemed it necessary. “I’m not an email person,” he said during a press conference in 2016. “I don’t believe in it because I think it can be hacked, for one thing. But when I send an email, if I send one, I send one almost never—I’m just not a believer in email.” He also reportedly did not own a personal or work computer before the election, and it’s unclear if he ever used one during his presidency. (He was, of course, conspicuously and constantly attached to his mobile phone; from time to time, his habits raised operational security concerns.)
Some of Trump’s proclivities could be explained by a personal aversion to modern technology, as well as the general power that rich people enjoy to make others accommodate their eccentricities. There may also be less benign explanations. In court filings last month, New York Attorney General Letitia James asked a judge to enforce her subpoenas against Trump and two of his adult children as part of an investigation into the Trump Organization’s financial records. James told the court that their testimony was necessary because Trump and his company had allegedly gone to great lengths to avoid creating a paper trail for their potentially improper activities.
“Evidence indicates that Mr. Trump adopted a practice of preventing the creation of written records with regard to his development efforts at Seven Springs,” James told the court, referencing a Trump property in Los Angeles. “One witness, who described his role as the ‘direct representative of Donald Trump’ for the Lower Hudson Valley testified that Mr. Trump directed his activities, that he spoke to Mr. Trump personally about Seven Springs ‘about once a week,’ and that he ‘seldom’ communicated in writing with Mr. Trump because Mr. Trump stated to him ‘that he did not want things put in writing in communications between us.’”
That strategy also extended to Trump’s closest employees, including his then-lawyer, Sheri Dillon. According to James’s court filing, Dillon was alleged “to have made efforts to avoid the creation of discoverable material” in potential future litigation by instructing people working with the Trump Organization to communicate almost exclusively by phone and to use email only when absolutely necessary. “Please use a fresh email when communicating with appraisers so that we avoid to the extent possible email chains,” Dillon told one witness. That witness told James that they understood the directive as a way to make it harder to reconstruct conversations if forced to turn over documents during the discovery phase of a future lawsuit.
These habits did not abate when Trump reached the White House, where federal law required him to preserve records from his presidency and transfer them to the National Archives. In 2018, Politico reported that Trump had a habit of tearing up official papers that were handed to him when he was done with them, even after being reminded multiple times that he was supposed to keep them intact. The problem reportedly grew so bad that multiple civil servants were tasked full-time to repair the documents with Scotch tape to comply with the Presidential Records Act.
At the time, this was largely dismissed as yet another bizarre behavior from one of the strangest people ever to serve as president. But his aversion to keeping a paper trail for the Trump presidency apparently had other consequences. The Washington Post reported earlier this month that Trump White House officials routinely used “burn bags” meant for classified material to incinerate a much wider range of White House records, often based on their personal discretion. According to the Post, this reportedly included documents about Trump’s efforts to pressure former Vice President Mike Pence to try to overturn the election results himself on January 6, something that the House January 6 committee learned during its inquiry.
There’s a deep and inescapable irony to all of this: Trump owes his presidency to another public official’s tangled relationships with public-records laws and classified information. Hillary Clinton, Trump’s 2016 opponent, faced multiple investigations over a private email server she used during her tenure as secretary of state, including inquiries into whether she mishandled classified information. Then–FBI Director James Comey’s eleventh-hour announcement, in October 2016, that the bureau had (briefly) reopened the investigation almost certainly led to her narrow defeat to Trump the following month, setting American history onto a much darker path.
Those who can vaguely remember the Clinton email investigation might also recall that the federal government’s rules for classified material are far from straightforward. It’s possible that Trump had material that wasn’t classified at the time or wasn’t marked as classified when he had it. And since the United States often has a habit of overclassifying things as secret, it’s probable that whatever he had was far more mundane than, say, the nation’s nuclear launch codes or the names of CIA operatives in foreign countries. That said, it was also reportedly serious enough that the National Archives felt it had to alert the Justice Department. The Post reported on Thursday afternoon that some of the recovered documents were clearly marked “top secret.”
The underlying message that my mom gave me as a child—don’t write things in haste that you might regret, don’t say things you can’t take back, always consider the potential audience for your words—was rooted in making sure I did the right thing. For Trump, his opposition to the written word appears to spring from a different goal: ensuring that there isn’t anything that federal prosecutors, journalists, or Congress can pin on him that he can’t simply spin or lawyer away.