John Bolton Indictment Explained: "Shhhhh!," 18 Espionage Charges, and AOL Email

How the Former NSA Who Called for Death Penalties for Leakers Now Faces the Same Charges—With Evidence Including 'Shhhhh' and All-Caps Messages

Who knew that the John Bolton indictment would be the most entertaining legal document I’d read in 2025? But here we are.

Let me break this down for you, because it’s equal parts serious and absurd.

The Bolton Indictment: What the DOJ Alleges He Did

The Department of Justice has charged Bolton, yes, that Bolton, the mustachioed Iraq War enthusiast who served as Trump’s National Security Advisor, with 18 counts under the Espionage Act. Eight counts for transmitting classified information, and ten for retaining it.

The basic story, per the indictment: Between April 2018 and September 2019, while Bolton was literally sitting in the White House Situation Room learning our nation’s most sensitive secrets, he was... emailing them to his wife and daughter. Via AOL. (okay boomer) And a messaging app. You know, like you’d share grocery lists or vacation photos.

Except instead of “don’t forget the milk,” it was stuff like “future attack plans by adversarial groups” and “sensitive intelligence sources and methods.” Classic diary material, really.

Oh, and then Iran allegedly hacked his personal email account. Because of course they did.

Bolton’s Past Statements on Classified Information Come Back to Haunt Him

Here’s where it gets chef’s kiss levels of ironic. Bolton has spent years publicly dunking on other people for mishandling classified information. The indictment helpfully catalogs his greatest hits, and folks—when I tell you the hypocrisy is wild...

When Bolton Called for the Death Penalty for Leaking Classified Information

Let’s start with the most extreme example, because it really sets the tone.

In 2012, when asked about Bradley Manning (now Chelsea Manning), who leaked classified documents to WikiLeaks, Bolton didn’t mince words:

BBC Interviewer: “What do you think of Bradley Manning?”

Bolton: “I think he committed treason. I think he should be prosecuted to the fullest extent of the law.”

Interviewer: “What does that mean?”

Bolton: “Well, treason is the only crime defined by our Constitution, and it says treason shall consist only of levying war against the United States or adhering to their enemies, giving them aid and comfort. And he gave our enemies a lot of aid and comfort.”

Interviewer: “So what should happen to him?”

Bolton: “Well, he should be prosecuted. And if he’s found guilty, he should be punished to the fullest extent possible.”

Interviewer: “And what is that?”

Bolton: “Death.”

Interviewer: “You think he should be killed.”

Bolton: “Yes.”

Just to be crystal clear: Bolton advocated for the death penalty for someone who leaked classified information.

Now, according to this indictment, Bolton was sending Top Secret/SCI information, including intelligence about foreign adversaries’ attack plans, sensitive sources and methods, and covert operations, to his wife and daughter via personal AOL email. Which was then hacked by Iran.

And then…

On Julian Assange: “176 Years”

Bolton was equally charitable toward Julian Assange. On Piers Morgan’s show, discussing Assange potentially facing extradition to the US, Bolton said:

“I think that’s a small amount of the sentence he actually deserves. He’s committed clear criminal activity. He’s no more a journalist than the chair I’m sitting on... I hope he gets at least 176 years in jail for what he did.”

One hundred and seventy-six years. For publishing leaked information.

Bolton, meanwhile, was planning to publish a book, The Room Where It Happened, based on those diary entries he’d been sending to family members. Entries that, according to the indictment, contained classified information at the highest levels. He literally started shopping the book around the day after leaving his position as National Security Advisor.

And then…

On Hillary Clinton’s Emails (2016):

Bolton literally tweeted: “If I had done what @HillaryClinton has done, I’d be in the slammer. #ClintonEmails”

He also told an interviewer in January 2017: “Look, as I’ve said before, I believe it still to this day, if I had done at the State Department what [senior U.S. Government official] did, I’d be [imprisoned] right now.”

And then…

On Trump’s Mar-a-Lago Documents (2022):

Bolton told CBS News that Trump’s handling of classified information “worried” him and showed “disdain for the seriousness of classification.”

He went further, saying:

“My concern was that he didn’t feel that the confidentiality of much of this information was as important as we knew it to be. It just didn’t register with him that safeguarding this information for its own sake, and because of the risk to sources and methods of obtaining the intelligence, could be jeopardized.”

This statement is now in the federal indictment as evidence that Bolton understood the severity of mishandling classified information.

And then…

On Using Personal Messaging Apps (March 2025):

In what might be the most perfectly aged statement in modern political history, Bolton said just this year:

“Well, I don’t, I mean, to me, I just can’t even imagine opening a Signal chat group or a Telegram chat group or anything else... You simply don’t use commercial means of communication, whether it’s supposedly an encrypted app or not for these kinds of discussions... there’s no excuse for it.”

And then…He had been using commercial means of communication for these kinds of discussions. For years. While it was happening.

No , and then…

Bolton’s ‘STUFF COMING!!!’

Can we talk about Bolton’s communication style for a second? Because the indictment reveals something I genuinely didn’t see coming: John Bolton texts like an enthusiastic teenager who just discovered caps lock.

According to the charging documents, Bolton would send messages to his family “editors” (yes, he called them that) with gems like:

• “STUFF COMING, BUT ONLY FOR [Individual 2]??? [Individual 1] TO READ HARD COPY WHEN [Individual 1] IS BACK IN US!!!!”

• “Stuff coming to cheer you . . . up!!!”

• “For Diary in the future!!!”

• “Shhhhh” (yes, he actually typed this after sharing sensitive information)

The excessive exclamation points! The random capitalization! The way he announces content like he’s posting a YouTube status update! This man had access to nuclear codes and was typing like he’d just discovered his first AOL chatroom in 1997.

Which, given that he was actually using AOL for this, might track.

There’s something darkly comedic about a man who advocated for the death penalty for leakers typing “Shhhhh” after emailing Top Secret information to his relatives.

Legal Analysis: How Strong Is the Case Against John Bolton?

Okay, setting aside the jokes for a moment (but only for a moment), I need to give you my completely unprofessional, definitely-not-a-lawyer assessment after reading this 26-page document and listening to actual legal experts weigh in.

Bolton is, in the technical legal parlance, pretty frickin’ cooked.

Here’s why I think that:

1. The Volume Is Damning We’re talking about over 1,000 pages of “diary entries” containing Top Secret/SCI information, sent to people with zero security clearance. This isn’t “oops, I accidentally took home a document.” This is a systematic pattern over 17 months.

2. He Literally Knew Better The indictment shows Bolton signed multiple non-disclosure agreements acknowledging that unauthorized disclosure of classified information “could cause damage or irreparable injury to the United States.” His own signature. On documents saying “don’t do the thing.” And then he did the thing. Repeatedly. With exclamation points.

3. His Own Words Doom Him Remember all those quotes about how serious mishandling classified info is? About how people deserve death or 176 years? The DOJ is using those as evidence that Bolton understood exactly what he was doing wrong. It’s like leaving a detailed confession, except you posted it on Twitter and cable news over several years.

When you’ve publicly said someone deserves to die for leaking classified information, and then you get caught doing something similar... that’s what lawyers call “bad facts.”

4. The Iran Hack Adds Real Consequences This isn’t theoretical damage. Iranian cyber actors allegedly accessed his personal email account, the same account he’d been using to send classified information. The government can point to actual, tangible national security harm. Iran, the country Bolton has spent decades positioning himself as the ultimate hawk against, potentially had access to his emails about U.S. intelligence operations.

5. Even Trump Critics Think This Is Serious When Eli Honig, a CNN legal analyst who’s been one of Trump’s harshest critics, writes an article titled “The John Bolton Indictment Is Different” and says Bolton is in “big, big trouble,” you know something’s up. Honig notes that unlike other Trump-era prosecutions, this one has serious underlying conduct and arose through normal investigative channels (the Biden administration had the case and didn’t charge him, remember).

The legal analysts I’ve been reading suggest conviction probability is pretty high. A plea deal to avoid prison time? Even more likely.

Trump, Retribution, and the Politics Behind the Bolton Prosecution

Look, I get it—there’s a whole conversation to be had about Trump’s motivations here, about selective prosecution, about whether this is “retribution” or “accountability.” Those are valid discussions.

But here’s what I keep coming back to: The evidence, as laid out in the indictment, is pretty straightforward. Bolton had classified information. He sent it to unauthorized people. On unsecured channels. That got hacked by a foreign adversary. While publicly demanding the death penalty for others who did similar things.

The Biden administration had this investigation. They didn’t charge him. That’s a political decision too, just in the other direction.

And the contrast between how Bolton talked about Manning, Assange, and Clinton versus his own conduct? That’s not a legal issue, that’s a character issue. But it sure doesn’t help his case in the court of public opinion.

My Actual Takeaway

Reading federal indictments shouldn’t be this entertaining, but here we are. The Bolton case is like if dramatic irony became a legal document. It’s genuinely difficult to imagine a more perfect example of “things that age poorly.”

Here’s a man who called for someone’s execution for leaking classified information, who wanted someone else imprisoned for 176 years for publishing leaks, and who spent years as a cable news fixture lecturing everyone about proper handling of secrets, caught doing the exact thing he condemned others for, except he did it via AOL while typing “Shhhhh.”

As for Bolton himself, he’ll get his day in court. That’s how this works. Maybe there’s a defense we haven’t seen yet. Maybe the “personal diary” argument holds water. (Spoiler: it probably doesn’t, but stranger things have happened.)

For now, I’m left with this image: One of America’s most hawkish national security voices, who spent decades in government service calling for maximum penalties for others, brought down by... AOL email and excessive exclamation points.