In a stunning development, former Trump administration official turned CNN anti-Trump talking head, John Bolton, had his home raided by the FBI early Friday morning. According to reports, the investigation is related to the alleged retention and leaking of classified documents, specifically regarding a memoir Bolton published in 2020.
SEE: Kash Patel's FBI Launches Early-Morning Raid of John Bolton's Home
Now, things have escalated further, with a second raid being carried out at Bolton's D.C. office.
🚨 MORE: FBI agents have raided John Bolton’s Washington, DC office, following the raid on his Maryland home earlier this morning. pic.twitter.com/Z7rYrytsb5
— Breaking911 (@Breaking911) August 22, 2025
This investigation isn't new. It stretches back to the first Trump administration, but it was quickly shuttered when Joe Biden took office. That happened despite there already being a grand jury involved, leading many to suspect that politics played a role in the decision. Sure enough, the Biden administration would later launch the Overton window into the sun by raiding Trump's Florida home, Mar-a-Lago, and charging him with the possession of classified documents.
While that case would later be shut down by a judge, the precedent was set, and it's probably one Democrats and their allies regret setting at this point.
Notably, at the time the Mar-a-Lago raid happened, Bolton was very critical of Trump regarding the situation. Appearing on MSNBC, he claimed that the president didn't "care about the classification system" and accused him of taking whatever he wanted.
3 years ago, John Bolton raced to a TV studio to criticize President Trump over classified documents.
— Steve Guest (@SteveGuest) August 22, 2025
"I don't think he cared about the classification system. I don't think he appreciated the sensitivity of this information. ... He liked cool things, he saw things that so he… https://t.co/JdnLBfilW2 pic.twitter.com/oojEbtann7
Well, I guess turnabout is fair play. Bolton probably never fathomed that Trump would regain the White House after Biden stepped in to save him. That's exactly what happened, though, and the Kash Patel-led FBI seems intent on holding Democrats to the standards they set. For Bolton, that could mean spending quite a long stint in prison.
🚨🚨 .@JonathanTurley estimates John Bolton could spend TEN YEARS in prison if convicted@DailyCaller pic.twitter.com/VX8PdLZur0
— Nicole Silverio (@NicoleMSilverio) August 22, 2025
How likely is that? I'd still chalk it up to not very likely. In fact, it's going to be very difficult to secure any conviction, no matter what evidence exists, because the D.C. judicial system and jury pool are so thoroughly compromised.
Recall that former special counsel John Durham lost his prosecution of Michael Sussmann despite providing literal receipts showing Sussmann worked for the Hillary Clinton campaign and charged her for the USBs he delivered false information to the FBI. The jury that gave that ridiculous verdict included three Hillary Clinton donors and a woman whose daughter played sports with Sussman's daughter.
SEE: John Durham Never Stood a Chance
So yeah, it's going to be tough to convict Bolton if he's ultimately charged, but that's almost beside the point. The process is part of the punishment, which is something Trump and his allies know all too well, having been targets of it for years on end.
Will a D.C. jury almost assuredly let Bolton and whoever else off the hook? Probably, but that doesn't mean the Trump administration shouldn't bother. They should absolutely bother and let the chips fall where they may.
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