WASHINGTON — Hillary Clinton’s presidential dreams were undermined by her use of a private email server that included classified information.
Donald Trump has risked criminal charges by refusing to return top-secret records to the government after leaving the White House.
And now misplaced files with classified markings has led to another investigation that’s causing a political and legal headache for President Joe Biden.

Jon Elswick, Associated Press
Letters concerning classified documents from House Oversight Committee chairman Rep. James Comer, R-Ky., to Debra Steidel Wall, archivist of the United States, and White House Counsel Stuart Delery are photographed Tuesday.
The three situations are far from equivalent. But taken together, they represent a remarkable stretch in which document management has been a recurring source of controversy at the highest levels of American politics.
For some, it’s a warning about clumsiness or hubris when it comes to handling official secrets. For others, it’s a reminder that the federal government has built an unwieldy — and perhaps unmanageable — system for storing and protecting classified information.
“Mistakes happen, and it’s so easy to grab a stack of documents from your desk as you’re leaving your office, and you don’t realize there’s a classified document among those files,” said Mark Zaid, a lawyer who works on national security issues. “You just didn’t hear about it, for whatever reason.”
Now Americans are hearing about it all the time. Political talk shows have been clogged with conversations about which papers were stashed in which box in which closet. Voters are getting schooled in intelligence jargon like TS/SCI, HUMINT and damage assessments.
Clinton’s email server was a dominant storyline of her presidential campaign, and the criminal investigation into Trump has clouded his hopes of returning to the White House.
Biden is facing scrutiny of his own after documents with classified markings were found at a former office in Washington and his home in Wilmington, Delaware. Republicans who recently took control of the House are preparing to investigate, and Attorney General Merrick Garland appointed a special counsel to in the Biden case, following a similar step he took with Trump in November.
“Investigations can quickly spiral,” said Alex Conant, a Republican political consultant. “For the Biden administration, having a prosecutor digging into these documents, you never know where that might lead.”
With overlapping investigations underway, there may be no end in sight for daily discussions of filing cabinets, storage rules and concerns about national security risks.
“The American people are very well aware of issues involving classified documents in part because we’ve been talking about them for almost eight years,” said Alex Conant, a Republican political consultant.

Kevin Lamarque, Associated Press
Then-Secretary of State Hillary Clinton checks her Blackberry from a desk inside a C-17 military plane upon her departure Oct. 18, 2011, from Malta, in the Mediterranean Sea, bound for Tripoli, Libya.
That’s when a House Republican committee investigating the attack on the U.S. consulate in Benghazi, Libya, discovered that Clinton had used a private email account while serving as secretary of state. The revelation led to a federal investigation that didn’t result in any charges, but 110 emails out of 30,000 that were turned over to the government were determined to have had classified information.
Trump, who pummeled Clinton over her handling of the emails, won the election and swiftly demonstrated carelessness with secrets. He memorably discussed sensitive intelligence with the Russian ambassador to the United States, leading to concerns that he may have jeopardized a source who helped foil terrorist plots.
After disputing the results of his election defeat, Trump left office in haphazard fashion, and he brought boxes of government documents with him to Mar-a-Lago, his Florida resort. Some of them were turned over to the National Archives, which is responsible for presidential records, but he refused to provide others.
Eventually the Justice Department, fearing that national security secrets were at risk, obtained a search warrant and found more top secret documents at the resort.
A special counsel was appointed to determine whether any criminal charges should be filed in the case or a separate investigation into Trump’s attempts to cling to power on Jan. 6, 2021, when a mob of his supporters attacked the U.S. Capitol.
Larry Pfeiffer, a former intelligence official, said the situation with Trump’s documents is far different than ones he encountered while working in government.
During the time that Pfeiffer was CIA chief of staff, classified files turned up in the wrong place in presidential libraries a handful of times, he said.
“It just happens,” said Pfeiffer, now director of the Michael V. Hayden Center for Intelligence, Policy and International Security at George Mason University. “Mistakes get made, and stuff gets found.”

Associated Press
This image contained in a court filing by the Department of Justice on Aug. 30, and redacted by in part by the FBI, shows a photo of documents seized during the Aug. 8 search by the FBI of former President Donald Trump's Mar-a-Lago estate in Florida.
He said that seems more likely to be the case regarding the documents with classified markings that were found at an office used by Biden at the Penn Biden Center for Diplomacy and Global Engagement after his term as vice president ended.
Biden’s personal lawyers discovered the documents and contacted the White House counsel’s office, and the National Archives picked up the records the next day.
The situation appears like “an average, run-of-the-mill mistake” that’s “being handled in a by-the-book, textbook fashion,” Pfeiffer said.
However, he said it would be wise for the government to review its practices for managing documents during transitions between administrations. It’s been six years since Biden left the vice president’s office, meaning classified records have been in the wrong place for a long time.
“That’s not a good thing, no matter how anyone is playing it,” he said.
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AP file
Then-President Donald Trump left the White House for Florida ahead of President-elect Joe Biden's inauguration. According to the General Services Administration, members of Trump's transition team were responsible for packing items into boxes, putting boxes on pallets and shrink-wrapping those pallets so they could be transported.
Prior to shipping, GSA said it "required the outgoing transition team to certify in writing that the items being shipped were required to wind down the Office of the Former President and would be utilized as the Office transitioned to its new location in Florida."
GSA did not examine the contents of the boxes and "had no knowledge of the contents prior to shipping," according to an agency spokesperson. GSA was also not responsible for the former president's personal belongings, which were transported by a private moving company.
Under the Presidential Records Act, presidential records are considered federal property — not private — and are supposed to be turned over to the National Archives and Records Administration. Multiple federal laws govern the handling of classified and sensitive government documents, including statutes that make it a crime to remove such material and retain it at an unauthorized location.
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AP file
After NARA realized that documents from Trump's presidency seemed to be missing from the material that it received as he left office, the agency requested the records from Trump on or about May 6, 2021, according to a heavily redacted affidavit made public Aug. 26, 2022.
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AP file
The special agent in charge of NARA's Office of the Inspector General sent a referral to the Justice Department via email after a preliminary review of the boxes revealed numerous classified documents.
"Of most significant concern," they wrote, according to a heavily-redacted affidavit released last week, "was that highly classified records were unfoldered, intermixed with other records, and otherwise unproperly (sic) identified."
After an initial review of the NARA referral, the FBI opened a criminal investigation into the matter.
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AP file
Trump's Save America PAC released a statement insisting the return of the documents had been as "routine" and "no big deal."
Trump insisted the "papers were given easily and without conflict and on a very friendly basis," and added, "It was a great honor to work with NARA to help formally preserve the Trump Legacy."
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AP file
The Justice Department sent a letter to Trump's lawyers seeking immediate access to the material, citing "important national security interest."
"Access to the materials is not only necessary for purposes of our ongoing criminal investigation, but the Executive Branch must also conduct an assessment of the potential damage resulting from the apparent manner in which these materials were stored and transported and take any necessary remedial steps," the department wrote.
Trump's lawyers requested an additional extension.
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AP file
Three FBI agents and a DOJ attorney went to Mar-a-Lago to collect additional material offered by a Trump attorney in response to the subpoena. They were given "a single Redweld envelope, double-wrapped in tape, containing the documents," according to an Aug. 30 filing.
That envelope, it was later found, contained 38 documents with classification markings, including five documents marked confidential, 16 marked secret and 17 marked top secret.
During the visit, the filing said, "Counsel for the former President offered no explanation as to why boxes of government records, including 38 documents with classification markings, remained at the Premises nearly five months after the production of the Fifteen Boxes and nearly one-and-a-half years after the end of the Administration."
Trump's lawyers also told investigators that all of the records that had come from the White House were stored in one location — a Mar-a-Lago storage room. Investigators were permitted to visit the room, but were "explicitly prohibited" from opening or looking inside any of the boxes, they reported, "giving no opportunity for the government to confirm that no documents with classification markings remained."
The Justice Department was also given a signed certification letter stating that a "diligent search" had been completed and that no documents remained.
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AP file
The Justice Department filed an application for a search and seizure warrant of Mar-a-Lago, citing "probable cause" that additional presidential records and records containing classified information remained in various parts of the club.
"There is also probable cause to believe that evidence of obstruction" would be found, read the heavily-redacted copy of the affidavit laying out the FBI's rationale for the search.
The Justice Department also revealed in the Aug. 30 filing that it had found 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."
U.S. Magistrate Judge Bruce Reinhart in South Florida approved the application that same day.
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AP file
The FBI executed the search at Mar-a-Lago, seizing 36 items of evidence, including boxes and containers holding more than 100 classified records, an order pardoning Trump ally Roger Stone and information about the "President of France."
Agents found classified documents both in the storage room as well as in the former president's office — including three classified documents found not in boxes, but in office desks.
They included items so sensitive that, "In some instances, even the FBI counterintelligence personnel and DOJ attorneys conducting the review required additional clearances before they were permitted to review certain documents."
"That the FBI, in a matter of hours, recovered twice as many documents with classification markings as the 'diligent search' that the former President's counsel and other representatives had weeks to perform calls into serious question the representations made in the June 3 certification and casts doubt on the extent of cooperation in this matter," the Justice Department wrote.
Trump and his allies, meanwhile, cast the search as a weaponization of the criminal justice system aimed at damaging him politically as he prepares for another potential White House run.
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AP file
Judge Reinhart unsealed the warrant that authorized the FBI to search Mar-a-Lago, which details that federal agents were investigating potential violations of three federal laws, including the Espionage Act.
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AP file
A highly redacted version of the affidavit laying out the FBI's rationale for searching Mar-a-Lago was released.
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Department of Justice via AP
The Justice Department responded to Trump's request for a special master in a filing that included new details about the investigation, including an assertion that classified documents were "likely concealed and removed" from a storage room at Mar-a-Lago as part of an effort to obstruct the probe.
It included a photograph of some the material found at the club, including cover pages of paperclip-bound documents — some marked as "TOP SECRET//SCI" with bright yellow borders and one marked as "SECRET//SCI" with a rust-colored border — splayed out on a carpet at Mar-a-Lago.
"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," Trump responded. "Thought they wanted them kept Secret?"