Trump foe John Bolton is set to plead guilty. Here’s why the case didn’t fall apart

As several criminal investigations into President Donald Trump’s foes continue to flail, federal prosecutors are now ushering one of his biggest critics to a conviction.

Trump’s former national security adviser John Bolton has agreed to plead guilty Friday to charges that he unlawfully retained sensitive national security information — marking a rare win in the Justice Department’s list of prosecutions against the president’s political enemies.

While several US attorneys have attempted to stand up cases against well-known political figures that Trump dislikes, the Bolton plea deal was secured by an understated but effective career prosecutor in Maryland, Kelly Hayes, who has been serving as US attorney since shortly after Trump took office last year.

“Everybody’s pleasantly surprised she’s still in the job,” one person who knows the office well said this week. “In some ways, she’s been trying to keep her head down … A lot of US attorney’s Offices tried to attract attention” of the White House.

Unlike cases against Trump’s other political enemies, like former FBI Director James Comey, Bolton’s case maintained support of career prosecutors and investigators.

Bolton’s plea deal — in which he admits to sharing sensitive national security information with his wife and daughter — amounts to one felony count that could result in prison time. The maximum sentence for the charge is five years.

Bolton has also agreed to pay a fine of a more than $2 million, sources told CNN. That fine amount could claw back much of the money Bolton earned from the sale of his memoir in 2020, which was deeply critical of Trump and which prompted the president to attack him publicly.

Maryland US Attorney Kelly Hayes’ approach, and the Bolton case itself, are viewed more seriously than the indictments and investigations of others who have faced federal charges at Trump’s urging, several sources familiar with the case and the office have told CNN.

Hayes also previously faced some pressure out of Washington, DC, to investigate California Sen. Adam Schiff, who hasn’t been charged with any crime. Assistant US attorneys in the office looked closely at the possibility of charging the senator related to his mortgage applications, and explained their hesitations to Justice Department leadership, people familiar with it told CNN. Schiff has repeatedly denied any wrongdoing.

Hayes was able to remove herself from political pressure, largely by staying out of the political limelight of the Trump era, and maintained relationships with Justice Department leaders, people familiar with the office say.

Bolton, in the end, is expected to admit to only a sliver of what federal law enforcement investigated. The plea agreement is narrowly focused on the information he is accused of sending to his wife and daughter.

The indictment accused him of 18 violations – eight counts of transmitting national defense information and 10 instances of illegal retention. His plea agreement will cut that down to one count of illegally retaining national defense information.

Bolton’s case, had it gone to trial, could have dragged significant classified information into the public eye.

Part of his decision to plead guilty was driven by a wish to avoid a trial — specifically one that had the potential to publicize sensitive information, according to a person familiar with his thinking.

In comments Bolton made after he was charged in October, he likened his prosecution to the horrific abuses of Joseph Stalin’s secret police and claimed he was “the latest target in weaponizing the Justice Department.”

Yet since the charges were unveiled last fall, the case has been viewed — even by critics of the Justice Department — as a legitimate prosecution decision.

Judge Theodore Chuang in Greenbelt, Maryland, will oversee his plea hearing on Friday and will likely ultimately sentence Bolton at a later date.

It’s expected that Bolton will advocate for no prison time, and the Justice Department may seek to jail him, setting up a major showdown at the sentencing, people familiar with the case say.

A Justice Department spokesperson on Thursday said that Bolton’s deal to plead guilty to a single criminal charge “is a common practice … and is in line with current DOJ charging and pleading policy.”

The spokesperson added that Bolton’s behavior that isn’t ultimately part of the charge on the books may be factored into conduct the judge reviews at his sentencing.

Bolton was accused of sending summaries and notes that included classified information to himself and to his immediate family at a time where he was keeping his own “archives,” and was frustrated by Trump’s leadership. The president ultimately fired Bolton in September 2019.

The former national security adviser discussed the notes extensively with his wife and daughter, as if they were editors, according to the indictment.

Then Bolton’s email account was hacked by Iranians. In 2021, his assistant reported it to the FBI, saying the hacker was threatening to expose sensitive government information, according to court filings.

“Good luck Mr. Mustache!” one message said, according to a person who described investigative documents.

The FBI and national security lawyers in Maryland and Justice Department headquarters formally opened an investigation in 2022 during the Biden administration.

Investigators soon discovered the diary-like entries he was sending himself — essentially his own notes on secret information he was learning during his time in the Trump White House, according to the indictment.

The case moved forward substantially last summer when investigators searched both his home in Maryland and his office in Washington, DC.

But not all of what they found played into the criminal allegations.

For instance, investigators recovered several documents from Bolton’s office that they believed could be classified or confidential. Those included plans and memos related to the US mission to the United Nations and diplomatic security during the 2000-2001 presidential transition, and records with headings that indicated they were about weapons of mass destruction. Bolton was in the State Department and was UN ambassador during the Bush administration.

The years-old records never became part of the case that Bolton faced.

Another part of the investigation into Bolton hinged on how he published his memoir of his time in the Trump White House, after a comprehensive review process where the Trump administration hadn’t given him the final approval to publish.

Ultimately, no classified information was included in the book.

“Bolton acquitted himself honorably and legally in the pre-publication review process,” Michael Bromwich, the attorney for Bolton’s pre-publication reviewer Ellen Knight, told CNN this week. “It was the way he handled classified information outside that process … that he will admit to.  It was sloppy and illegal but not sinister.”