The investigation into President Trump’s former national security adviser, John R. Bolton, began to pick up momentum during the Biden administration, when U.S. intelligence officials collected information that appeared to show that he had mishandled classified information, according to people familiar with the inquiry.
The United States gathered data from an adversarial country’s spy service, including emails with sensitive information that Mr. Bolton, while still working in the first Trump administration, appeared to have sent to people close to him on an unclassified system, the people said, speaking on the condition of anonymity to discuss a sensitive case that remains open.
The investigation of Mr. Bolton, who has become an ardent critic of the president, burst back into public view last week when federal agents searched his Maryland home and Washington office.
While those searches have raised fresh questions about the extent to which Mr. Trump may be using the Justice Department and F.B.I. to try to punish those he dislikes, the new details of the case present a more complex chain of events. The disclosures suggest that a long-running investigation into Mr. Bolton’s activities changed over time, with some of the issues echoing past inquiries into the handling of national security secrets.
The emails in question, according to the people, were sent by Mr. Bolton and included information that appeared to derive from classified documents he had seen while he was national security adviser. Mr. Bolton apparently sent the messages to people close to him who were helping him gather material that he would ultimately use in his 2020 memoir, “The Room Where It Happened.”
In a sign of the stakes for Mr. Bolton, he is in talks to retain the high-profile criminal defense lawyer Abbe Lowell. Mr. Lowell, who has represented Mr. Trump’s son-in-law, Jared Kushner, and Mr. Biden’s son Hunter, is defending two other prominent perceived enemies of Mr. Trump who are now under scrutiny: the New York state attorney general, Letitia James, and Lisa Cook, a member of the Federal Reserve Board.
No charges have been filed against Mr. Bolton. One major reason for conducting the searches was to see if Mr. Bolton possessed material that matched or corroborated the intelligence agency material, which, if found, would indicate that the emails found in the possession of the foreign spy service were genuine, the people said.
A Justice Department spokesman declined to comment. Through a representative, Mr. Bolton declined to comment.
Two federal judges authorized the warrants for the F.B.I. to conduct the searches. To obtain the search warrants, prosecutors would have had to show that they had reason to believe that Mr. Bolton possessed evidence that showed he could have mishandled classified information.
Shortly before Mr. Bolton’s book was published, the Trump administration went to court seeking to delay its release. The Justice Department around that time also opened a criminal investigation into whether Mr. Bolton had mishandled classified information by disclosing certain details in the book. A judge later concluded he may well have published classified information, but the criminal investigation seemed to languish until the intelligence about his emails was gathered years later.
It is not clear what country intercepted Mr. Bolton’s private emails, but Iran, Russia and China all would have had intense interest in his communications while he was the national security adviser. Because of his role in helping Mr. Trump kill a top Iranian general, Mr. Bolton had a security detail to protect him from potential Iranian retaliation, but Mr. Trump abruptly ended it the day after he was sworn in for his second term.
During Mr. Trump’s second term, John Ratcliffe, the C.I.A. director, briefed Kash Patel, the F.B.I. director, on the information that had been collected about Mr. Bolton’s emails. The officials believed that the material Mr. Bolton had transcribed into the unclassified and unsecured email contained classified information. Each intelligence agency makes its own determinations about what information is classified, so it is often up to the “originating” agency to decide whether particular pieces of information are classified, and how sensitive they are.
The material in the intercepted emails included information that Mr. Bolton did not ultimately use in his book. That may suggest that he had been told it remained classified during early reviews of his manuscript or that he ultimately decided to omit it, because of either its sensitivity or its importance.
Investigations of possible mishandling of national security secrets are nothing new. The law Mr. Bolton is being investigated under, the Espionage Act, was passed in 1917. But in recent years, such cases have taken on an outsize role in American politics.
During the 2016 presidential campaign, Hillary Clinton was investigated for her use of a private email server to handle her duties as secretary of state. In 2022, F.B.I. agents searched Mr. Trump’s Mar-a-Lago home in Florida and found more than 100 classified documents, in addition to other ones retrieved earlier. Mr. Trump was indicted in that case, but the charges were dismissed by the trial judge during the 2024 presidential campaign. And in early 2023, the Justice Department appointed a special counsel to investigate how classified documents had ended up in President Joseph R. Biden Jr.’s office and home after he left the vice presidency.
Devlin Barrett covers the Justice Department and the F.B.I. for The Times.
Julian E. Barnes covers the U.S. intelligence agencies and international security matters for The Times. He has written about security issues for more than two decades.
Michael S. Schmidt is an investigative reporter for The Times covering Washington. His work focuses on tracking and explaining high-profile federal investigations.
Glenn Thrush covers the Department of Justice for The Times and has also written about gun violence, civil rights and conditions in the country’s jails and prisons.
Maggie Haberman is a White House correspondent for The Times, reporting on President Trump.
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