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By Andrew Stanton
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John Bolton, who served as President Donald Trump’s national security adviser during his first term in office, pleaded guilty to mishandling classified information on Friday, joining the list of Trump associates who have been involved in crimes.
Bolton pleaded guilty to one count of illegally retaining classified information after being charged last October with 18 counts of retaining or disseminating classified information. The plea deal could help him avoid prison time, capping his sentence at five years.
Prosecutors accused Bolton of sharing more than 1,000 pages of notes with two family members who lacked security clearances. He allegedly routinely transcribed his handwritten notes into lengthy documents and sent them through personal email accounts and a commercial messaging app.
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Bolton served in Trump’s administration for more than a year from 2018 to 2019 and has become a vocal critic of Trump since leaving office. He published his memoir, The Room Where It Happened, in which he detailed critical accounts of the Trump presidency, in 2020.
Former federal prosecutor Neama Rahmani told Newsweek on Friday that these charges are "pretty serious," particularly for a former national security adviser. Still, Bolton is unlikely to face prison time for this case, he said.
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“I would be surprised if he was sentenced to a term of imprisonment. It’s not like he sold these secrets or provided them to a foreign adversary or anything like that,” he said, also noting that Bolton has no prior criminal history and is 77 years old.
He said the case is more legitimate than that of other Trump adversaries like former FBI Director James Comey, which he described as “pretty ridiculous.”
Trump reacted to Bolton pleading guilty in a post to Truth Social late Friday night saying, "John Bolton, a very dumb, unbalanced, and unskilled former representative of the United States of America, just pleads guilty! He is a terrible person, a lunatic who only wanted to start trouble and wars, and who was a needless pusher of death and destruction wherever he went. Hopefully, he will be dealt with harshly! President DJT"
Numerous officials and associates of Trump have faced legal issues over the past decade. Here is a look at where those individuals are now:
Steve Bannon
Bannon served as a strategist and counselor to Trump during his first term in office. In 2022, he was convicted of defying a subpoena to testify in front of the January 6 House Select Committee, which investigated the violent protests of Trump’s supporters at the U.S. Capitol over his 2020 electoral loss.
Bannon was released from prison after serving four months in 2024. He remains a vocal Trump supporter and is influential in conservative politics as the host of the War Room podcast.
Michael Cohen
Cohen was Trump's longtime personal attorney and pleaded guilty to campaign finance and tax violations related to a hush-money payment made during Trump’s 2016 presidential campaign. He later pleaded guilty to making false statements to Congress about plans to build a Trump Tower in Moscow.
He served a little over one year in prison before being released to home confinement during the COVID-19 pandemic in 2020. He completed his sentence in November 2021.
Cohen has become a frequent and vocal critic of Trump. He suggested he could apply for the DOJ’s anti-weaponization fund before acting Attorney General Todd Blanche said the administration would no longer be pursuing it.
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Peter Navarro
Navarro, who served as a White House trade adviser, was sentenced to four months in prison in 2024 after refusing to testify in congressional investigations into the January 6 attack. He was released from prison in July 2024. He serves as senior counselor to Trump for trade and manufacturing in Trump’s second term.
Michael Flynn
Flynn, a retired lieutenant general who served as Trump’s national security adviser, pleaded guilty in December 2017 to making false statements to the FBI about his communications with a Russian ambassador during the presidential transition. Trump issued a pardon to Flynn in 2020 before leaving office.
He remains active in conservative politics, with Trump appointing him to the West Point board of visitors in 2025. Earlier this year, he reached a $1.2 million settlement with the DOJ resolving a lawsuit in which he claimed he was wrongfully and maliciously prosecuted during the Russia investigation.
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Tom Barrack
Barrack, a senior adviser to Trump's 2016 presidential campaign, was charged but found not guilty in 2022 of acting as an unregistered foreign agent. He now serves as the ambassador to Turkey.
Paul Manafort
Manafort, who chaired Trump’s 2016 campaign, served a two-year prison sentence after being convicted of tax fraud, bank fraud and illegal lobbying. He was released to home confinement in May 2020 amid the pandemic. The New York Times reported in 2025 that he was considering political roles in Latin America and Europe.
George Papadopoulos
Papadopoulos worked on Trump’s 2016 campaign and pleaded guilty to lying to the FBI in connection with the Russia investigation. He allegedly suggested that he coordinate a meeting between Trump and Russian leadership during the campaign.
He served 12 days in prison and was later pardoned by Trump in December 2020. He ran for Congress in 2020 but received less than 3 percent of the vote.
Rick Gates
Gates, a Trump adviser, also pleaded guilty to making false statements and conspiracy against the United States in connection with the Russia investigation. He was accused of money-laundering, lying to investigators and other charges and faced the potential of decades behind bars.
He cooperated with special counsel Robert Mueller’s probe into Trump and his associates’ ties to Russia. He has kept a lower profile in the years since.
Rudy Giuliani
The former mayor of New York served as Trump's personal attorney during the president's first term and helped lead the legal effort to challenge the 2020 election results.
He was indicted in Georgia in August 2023, alongside Trump and 17 other co-defendants, on state charges stemming from efforts to overturn the 2020 election. He pleaded not guilty. In May 2024, he also pleaded not guilty in Arizona to similar charges of conspiring to overturn the 2020 results.
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A federal jury ordered Giuliani in December 2023 to pay nearly $150 million to former Georgia election workers Ruby Freeman and Shaye Moss for defamation, and he filed for bankruptcy later that month. The case was dismissed by a judge in July 2024.
Giuliani spokesman Ted Goodman revealed in May that the former mayor was recovering from pneumonia. He said Giuliani developed restrictive airway disease after running toward the World Trade Center towers on September 11, 2001, to help others, a condition that complicates respiratory illnesses
Trump 2020 Election Challenge Lawyers
Several Trump lawyers, such as Sidney Powell, Jenna Ellis and Kenneth Chesebro, were charged in an Atlanta-area investigation into his alleged efforts to thwart the election results in Georgia, a state he narrowly lost to Democrat Joe Biden.
All three were pardoned by Trump in 2025.
Ellis, whose Colorado law license was suspended for three years, remains a political commentator with a show on American Family Radio. Earlier in June, the Florida Supreme Court declined to suspend Chesebro’s law license.
Roger Stone
Stone, a Trump adviser, was found guilty of charges including obstructing a congressional investigation into alleged Russian interference in the 2016 election. He was found guilty of obstruction of a congressional investigation, five counts of making false statements to Congress and tampering with a witness. He remains an active lobbyist amid Trump’s second term in office, Politico reported in April.
Allen Weisselberg
Weisselberg, a former Trump Organization executive, served time in New York's Rikers Island jail after being convicted of perjury and was released in July 2024. He had pleaded guilty to two counts of lying under oath during his testimony in Trump's civil business fraud trial. Weisselberg earlier served a separate 100-day stint at Rikers Island for tax evasion on $1.7 million in company perks.
He has kept a low profile after his release.
This article includes reporting by the Associated Press.
Contact Newsweek editors on this story: Gabe Whisnant, Sam Wilson, Anna Commander and Gray R. Thomas
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