(GREENBELT, Md.) — President Donald Trump’s former national security adviser John Bolton is expected to plead guilty Friday to mishandling classified information.

Bolton, who arrived in federal court in Maryland Friday morning, is expected to plead guilty to one count of illegal retention of sensitive documents, sources have told ABC News.

Bolton has also agreed to pay a fine of $2.25 million, sources said.

The count he is pleading guilty to involves keeping classified national security information in diaries, according to sources. Bolton is expected to maintain that he did not take documents with classification markings out of government offices.

The guilty plea would make Bolton thus far the only successfully prosecuted case in Trump’s campaign of retribution against those he perceives to be his political enemies.

Bolton, who was national security adviser for part of the first Trump administration, was indicted by a grand jury in October 2025 on charges that he allegedly unlawfully transmitted and retained classified documents.

The indictment, handed up by a federal grand jury in Maryland, charged Bolton with eight counts of unlawful transmission of national defense information as well as 10 counts of unlawful retention of national defense information.

Prosecutors had accused Bolton of using a non-government personal email account and messaging application to transmit to two unauthorized family members at least eight documents that contained information classified at levels ranging from “secret” to “top secret.”

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(NEW YORK) — Private equity billionaire Leon Black is set to face questions Friday from the House Oversight Committee regarding his decades-long relationship and sprawling financial entanglements with convicted sex offender Jeffrey Epstein.

The latest in a series of rich and powerful people questioned about their relationship with Epstein as part of the House Oversight panel’s ongoing probe, Black maintained a social relationship with Epstein since the mid-1990s and eventually paid him more than $170 million for “tax and estate planning advice,” according to the Senate Finance Committee.

Black has denied wrongdoing or knowledge of Epstein’s crimes, though his financial payments to Epstein served as a lifeline to the convicted sex offender in the years after Epstein’s 2008 prison sentence for soliciting a minor for prostitution. Sen. Ron Wyden, the ranking member of the Senate Finance Committee, has argued that Black has so far failed to provide a credible explanation for the payments and may have been “extorted” by Epstein.

“Leon Black was one of Jeffrey Epstein’s primary sources of income, flooding him with cash at a time when he was already a registered sex offender. Black has not yet offered a compelling explanation regarding the origination and execution of Epstein’s extraordinary compensation scheme for alleged tax advice,” Wyden wrote in a letter to the House Oversight Committee earlier this month. The Senate Finance Committee is leading its own investigation of Epstein’s finances.

Black has long been scrutinized over his relationship with the disgraced financier — describing it as a “horrible mistake” — and was forced out of his firm Apollo Global Management following an external investigation that revealed payments to Epstein totaling at least $158 million.

“Knowing all that I have learned in the past two years about Epstein’s reprehensible and despicable conduct, I deeply regret having had any involvement with him,” Black said during a 2020 Apollo earnings call. “With the benefit of hindsight, working with him was a horrible mistake on my part. I am not seeking to excuse that decision, but I do believe it may be helpful to convey some relevant facts.”

While the investigation concluded that Black and others were aware of Epstein’s 2008 conviction, a report summarizing its findings said that Black was not “involved in any way with Epstein’s criminal activities at any time” or aware of the “scope and details” of Epstein’s sex trafficking. Black has never been charged with a crime.

“When Black first retained Epstein, he believed that Epstein had served his time for the originally charged offenses and believed that it was not inappropriate to give Epstein a second chance, as many other prominent figures in business, science, politics and academia had done,” the report said.

The release of the Department of Justice’s Epstein files earlier this year cast more scrutiny on Black, whose name appears in the files more than 8,000 times. Epstein at one point appeared to serve as a middleman to pay $100,000 to a woman with whom Black allegedly had an affair, according to emails included in the files, and routinely served as a fixer for issues involving his finances.

“Leon, as you are well aware, there is little I won’t do for you or at least try to do as a friend, and a great deal that I have already done (both known and some things that will need to remain unknown),” Epstein wrote to Black in a 2014 email. In another email in 2017, Epstein described his relationship with Black as “saving you from yourself.”

In a statement to ABC News, Black’s attorney Susan Estrich pointed to the external investigation conducted for Apollo that found Black “had no awareness of the criminal activities that led to Epstein’s arrest in 2019” and noted that Black has called for an independent investigation of his relationship with Epstein.

Wyden of the Senate Finance Committee has called on the House Oversight members to scrutinize the $170 million that Black paid Epstein between 2012 and 2017 for purported tax and estate planning. According to Wyden, those payments are sixty times more than what Epstein paid his other tax and estate professionals during the same timeframe.

“Black is a well-advised businessman with access to sophisticated attorneys, yet it appears Epstein was able to shake him down for money that he wasn’t legally owed. This suggests that Epstein may have extorted Black or performed other unseemly tasks on his behalf,” Wyden wrote.

According to the 2021 external report, Epstein was paid proportionally to the amount of money he saved Black and that Epstein “provided advice that conferred more than $1 billion and as much as $2 billion or more in value to Black”; however, the report also acknowledged that Epstein’s advice was often not useful and that he was “generally a disruptive and caustic force.”

The external report said investigators found “no evidence suggesting that Black ever compensated Epstein for any service other than Epstein’s legitimate advice on trust and estate planning” and other issues.

Wyden urged the House Oversight Committee to question Black about the basis for those payments and argued he has seen “no proof” that Epstein’s compensation was tied to a percentage of the Black’s estate tax liability he saved.

“To date, I do not believe Black has provided a credible explanation as to why he paid Epstein amounts that vastly exceeded those paid to other professional advisors involved in his tax and estate planning,” he said.  

Black also paid a $62.5 million settlement to the United States Virgin Islands in 2023 after acknowledging that Epstein used the money to “partially fund his operations in the Virgin Islands,” where Epstein owned a private island. Wyden urged the House Oversight panel to press Black about whether he was ever under criminal investigation and if that money was used to fund sex trafficking.

Attorneys for Black have pushed back against Wyden’s accusations, accusing him of harassment and saying that the billionaire has cooperated “voluntarily and without compulsion.”

“We are aware of no other private citizen subjected to more written requests from you over the same period,” Black’s attorneys wrote in an April 2026 letter to Wyden. “Your continued attempts to invade into matters pertaining to Mr. Black’s personal life — without the support of any legitimate legislative purpose — appear targeted to unfairly harass Mr. Black in a manner that completely disregards the proper scope of Congress’s investigative powers.”

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