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After the F.B.I., during the 2016 presidential campaign, investigated Hillary Clinton’s handling of classified material while she was secretary of state, Mr. Trump assailed her, helping make the issue pivotal in the outcome of that race. In that case, the intelligence community’s inspector general had made a national security referral to the F.B.I., prompting the investigation of Mrs. Clinton.

But during Mr. Trump’s administration, top White House officials were deeply concerned about how little regard Mr. Trump showed for sensitive national security materials. John F. Kelly, the White House chief of staff, tried to stop classified documents from being taken out of the Oval Office and brought up to the residence because he was concerned about what Mr. Trump may do with them and how that may jeopardize national security.

Similar to Mrs. Clinton, Mr. Trump’s son-in-law, Jared Kushner, and daughter Ivanka used personal email accounts for work purposes. And even after being warned by aides, Mr. Trump repeatedly ripped up government documents that had to be taped back together to prevent him from being accused of destroying federal property.

Now Mr. Trump faces questions about his handling of classified information — a question that is complicated because as president he had the authority to declassify any government information. It is unclear whether Mr. Trump had declassified materials the National Archives discovered in the boxes before he left office. Under federal law, he no longer maintains the ability to declassify documents after leaving office.

He invoked the power to declassify information several times as his administration publicly released materials that helped him politically, particularly on issues like the investigation into his campaign’s ties to Russia.

Toward the end of the administration, Mr. Trump ripped pictures that intrigued him out of the President’s Daily Brief — a compendium of often classified information about potential national security threats — but it is unclear whether he took them to the residence with him. In one prominent example of how he dealt with classified material, Mr. Trump in 2019 took a highly classified spy satellite image of an Iranian missile launch site, declassified it and then released the photo on Twitter.