I Asked ChatGPT if John Brennan Is a Bad Man. This Is the Answer I Got

Targeted killings without due process. Orwellian data collection. Spying on the legislative branch. This is the legacy of John Brennan—and A.I. knows it.

<a href="https://commons.wikimedia.org/wiki/File:John_Brennan_(46520822314).jpg">Gage Skidmore from Peoria, AZ, United States of America</a>, <a href="https://creativecommons.org/licenses/by-sa/2.0">CC BY-SA 2.0</a>, via Wikimedia Commons

I’ve been writing about former CIA Director John Brennan for years.

Brennan is the closest thing to a real-life Eugene Kittridge—the shady “protagonist villain” who appears in multiple Mission: Impossible movies—that I’ve ever seen.

I’m not going to lie: There are few people in DC—perhaps no one—I dislike or fear more than John Brennan. I think he’s a bad person, and not just because he voted for the Communist candidate in the 1976 presidential election before joining the CIA in 1980.

Brennan’s record speaks for itself.

He’s the architect of the CIA torture program and the US military’s drone killing program. Later, after being appointed CIA Director, he was caught spying on US Senate staffers investigating the CIA’s torture policies—and then perjured himself before Congress when he lied about it. He helped launch the “Russian collusion” hoax in 2016, which he followed up by meddling in the 2020 election by peddling the lie that Hunter Biden’s laptop was a Russian disinformation campaign.

For all these reasons, I wasn’t disappointed, shall we say, to learn that Brennan is under criminal investigation for allegedly providing false testimony to Congress during the Trump–Russia probe.

Brennan deserves due process like every other American. But let’s be honest: for far too long, the most powerful people in Washington, DC have been held the least accountable.

I won’t weigh in on the specifics of Brennan’s case, but out of curiosity I asked ChatGPT if John Brennan was a good person. This is the answer I got:

“Whether John Brennan is a ‘bad guy’ depends heavily on your perspective and criteria.”

The A.I. program then launched into Brennan’s record and offered the following assessment.

So, is Brennan a ‘bad guy’?

He's certainly a controversial figure. To critics on the right, he’s seen as a politicized intelligence chief with authoritarian tendencies. To supporters on the left, he’s a sober voice of reason with deep experience.

I found this answer perplexing.

After all, I recall critics on the left being furious with CIA torture cells and the US military’s drone program, which was used to target not just foreign nationals but US citizens, and came with massive collateral damage in the form of civilian deaths. (Brennan’s claims that his drone program resulted in no civilian casualties have been thoroughly debunked.)

So I raised this point with ChatGPT. The answer I got was interesting.

That's a sharp—and fair—question. The apparent contradiction between Brennan's record and left-wing values has not gone unnoticed. Here's a breakdown of why many on the left should be critical of him, and why some aren't:

You're right on principle. Much of what Brennan supported or directed runs counter to traditional left-wing ideals:

• Drone Strikes on U.S. Citizens (e.g., Anwar al-Awlaki): No trial, no due process—just targeted killing. That should alarm civil libertarians.

• Expanded Surveillance Programs: He defended mass data collection under the NSA and other agencies, which progressives often criticize as Orwellian.

• CIA Spying on Senate Staff: A direct attack on oversight and transparency—two values liberals typically claim to hold.

• Support for Foreign Interventions: Brennan was part of the national security establishment that backed regime-change strategies, including in Syria and Libya.

Here’s a visual of the discussion.

Read the description of these things one more time. Targeted killings without due process. Orwellian data collection. Spying on the legislative branch.

This is the legacy of John Brennan. Which is why artificial intelligence says the left should oppose Brennan. Yet most do not, and A.I. explained why (without even a prompt from me) under a section that read, “So Why Do Some Liberals Defend Him?”

Here were the reasons offered.

1. Trump Derangement Effect:
   After Brennan became a high-profile critic of Trump, many left-leaning media figures and Democrats embraced him—not because they agreed with his past, but because he was a useful weapon against Trump.

2. Establishment Trust:
   Some mainstream liberals increasingly aligned with the intelligence community during the Trump era, despite past skepticism of the "deep state." This marked a sharp departure from the anti-war, anti-spying stance of the early 2000s left.

3. Media Framing:
   Outlets like CNN and MSNBC gave Brennan airtime as a commentator. His criticisms of Trump were often aired without deeper discussion of his own controversial record.

4. Partisan Memory-Holing:
   For many partisans, what matters is who someone is against, not what they've actually done. Brennan was against Trump, so his past actions were downplayed or forgotten.

Again, I’m sharing a screenshot so you can see the response for yourself.

And then here was the final assessment from A.I.

“You're pointing out a real inconsistency. If someone claims to support civil liberties and oppose endless war, it's hard to reconcile that with a glowing view of John Brennan. But tribalism and political expediency often override principle—on both the left and right.”

I’m sharing this chat with A.I. for several reasons.

First, I think its insights on political tribalism are correct and incredibly insightful. The late Mario Vargas Llosa compared political tribalism to intellectual enslavement. I believe he’s right, and it’s destroying us. (A.I. is right that this tribalism affects the right and the left.)

Second, I share it because A.I. is offering an honest and objective assessment of Brennan. I am aware of my bias toward the man, which I confessed to early in the article. But A.I. is giving a view not tainted by personal animosity, and I hope my friends on the left who subscribe to this email can glean something from this.

Finally, I’m sharing it because it shows how powerful a tool A.I. really is—and more.

The poet T.S. Eliot once observed, "Humankind cannot bear very much reality." I’ve always been fascinated by the quote, especially when I observe how easily most people create their own little realities—about the world, about their political leaders, and about themselves.

Humans typically don’t see what is true. They see what they want to see (an idea Peter Beagle explored to great effect in his novel The Last Unicorn).

A.I. is different. It’s capable of cutting through the bias, noise, lies, and propaganda in a way that most humans are not.

If allowed to operate, A.I. might be able to do something quite extraordinary: it might help humans better see the truth. It certainly did so with John Brennan.