Can You Reason With Monsters Like Hitler?

A Note from James:

Bill O’Reilly’s new book, Confronting Evil, is both a history lesson and a warning. It’s a study of the most destructive figures in human history—from Hitler, Stalin, and Mao to Genghis Khan, Caligula, and even modern evildoers like Putin and the cartels.

When I first picked it up, I thought it would be about the past. But after reading it, I realized it’s really about right now—about how evil mutates, reappears, and spreads when we stop paying attention.

We talked about the psychology of evil, how it manifests differently in modern life, and why we all need to look inward at how we process fear and anger. The episode ends on a note of hope—but only if we’re willing to face what’s real.

Episode Description:

In this episode, James sits down with legendary journalist and author Bill O’Reilly to discuss his new book, Confronting Evil: Assessing the Worst of the Worst. Together, they explore how history’s darkest figures—Hitler, Mao, Stalin, Putin, and others—reflect modern patterns of violence, polarization, and moral decay.

O’Reilly draws from decades of reporting and war correspondence to explain the difference between “personal evil” and “collective evil,” and why societies collapse when good people stop paying attention.

The conversation also looks at free speech, mental illness, the internet’s role in radicalization, and why mercy for the guilty so often becomes cruelty to the innocent.

What You’ll Learn:

• The 15 most destructive figures in world history—and why their patterns are repeating today.
• The two types of evil: personal vs. collective.
• How technology and echo chambers amplify hatred.
• Why ignoring small evils allows larger ones to grow.
• How to recognize and contain evil in a free society.

Timestamped Chapters:

• [02:00] A Note from James: Introducing Confronting Evil
• [02:39] Are we living in a new age of violence or just a repeating cycle?
• [03:39] On partisanship, anger, and how fear disguises itself
• [04:57] Bill joins: marketing a book in the age of distraction
• [05:51] Why O’Reilly wrote Confronting Evil and how it differs from his “Killing” series
• [07:16] Putin, October 7th, and the eerie timing of the book’s release
• [08:20] Why today’s evil feels more personal than historic evil
• [09:39] Personal encounters with evil: chasing Ted Bundy
• [11:01] Witnessing atrocities: from El Salvador to Belfast
• [12:24] Could Hitler have been reasoned with? The psychology of the irredeemable
• [14:27] “Mercy to the guilty is cruelty to the innocent” — justice and accountability
• [15:36] The internet’s role in radicalization and digital “clubs for evil”
• [17:00] Echo chambers, hate speech, and how the free world handles extremism
• [19:02] Why confronting evil matters in a “free” but apathetic society
• [20:00] The October 7th attacks and why O’Reilly opens his book there
• [21:22] “Queers for Palestine” and the IQ of modern activism
• [22:00] How ignorance and apathy breed delusion
• [23:00] When does “necessary evil” cross the line into tyranny? Augustus and strongmen
• [25:10] The psychology of dictators: no remorse, no redemption
• [26:11] The Constitution as an anti-authoritarian framework
• [27:50] Polarization, Portland, and the fight over federal authority
• [29:00] How democracies correct themselves—eventually
• [31:31] Data over ideology: why extremists are still a minority
• [32:04] Can AI detect future Hitlers?
• [33:28] Why people cheer for evil—and how to walk away
• [34:46] The 15 who made the cut: why some evildoers were left out
• [35:36] The drug cartels as modern-day mass murderers
• [36:29] O’Reilly’s warning: mobilize the 85% before it’s too late
• [36:54] Ending on hope—why good still outnumbers evil

Additional Resources

• 📖 Confronting Evil: Assessing the Worst of the Worst by Bill O’Reilly & Josh Hammer
• 📚 BillOReilly.com – Official Site
• 🎧 Related: The James Altucher Show – Charles Duhigg on Super Communicators

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