Great book... like most of O’Reilly’s. I flew through it. The writing style is fast, engaging, and moral in tone, just like his Killing series. But I couldn’t tell if O’Reilly was trying to highlight the most evil men in history or simply present a sampling of evil across different eras, religions, and types of power. It feels like he was trying to do both and that’s where the structure begins to blur.
He leans heavily on modern figures and household names while ignoring men who were, by almost any standard, far more sadistic and depraved. Think serial killers. People who didn’t just cause death, but enjoyed it. There’s a big difference.
That’s one of the weaknesses of the book: simplification and selective framing. Because O’Reilly’s trying to cover such a huge span of history and make these broad moral claims, the details get flattened. The nuances... the gray areas of human behavior, contested motives, and the messy legacies are mostly brushed aside. It turns into a “good guy vs. bad guy” narrative, which is emotionally satisfying but not intellectually honest.
My biggest disagreement was with his assessment of Nathan Bedford Forrest.
While slavery itself is undeniably evil, and the Confederate cause was morally bankrupt, Forrest wasn’t altogether evil as a man. O’Reilly paints him with the same brush as monsters like Hitler and Caligula, and that’s just sloppy. Forrest fought brutally for an evil cause, yes... but the man also changed. Even though he was called the father of the KKK, the organization he founded wasn’t created as a racist death cult. It was initially meant to protect Southerners, especially returning Confederate soldiers and their families from Union retribution. Once it morphed into the hate-driven terror group we know today, Forrest left it and denounced it publicly. That’s not something you do if you’re the embodiment of evil. Was O’Reilly pandering? Posturing? Maybe. But Forrest didn’t belong in that company.
In sheer numbers, O’Reilly is right on Mao, Stalin, Hitler, and Genghis Khan... those four are the cornerstones of mass-scale, impersonal evil. I also liked that he included the drug cartels because they represent a different kind of darkness, greed and violence without ideology. But including figures like Putin, the Robber Barons, and the Ayatollah weakened the premise. Yes, they’re evil men in their own ways, but they’re not in the pantheon of the most evil men in the history of the world. Their inclusion felt like a reach to keep things “relevant” for modern readers.
Caligula and Henry VIII were interesting choices and new to me in this context. Both fit because they personify the corruption of absolute power, but then O’Reilly throws in the Robber Barons, and it just feels off. Ruthless businessmen don’t belong in the same chapter as genocidal tyrants. If he wanted variety, he could’ve drawn from history’s countless sadists and predators.... Ted Bundy, Bloody Mary, Gilles de Rais, and others who embodied personal evil, not systemic.
And that, to me, is the key point the book misses:
Evil isn’t measured only by how many people die. It’s measured by how and why they suffer. The intimate act of sadism... the pleasure of personally inflicting pain for gain or enjoyment. That is a deeper evil than detached political cruelty. There’s a difference between a man who signs orders that lead to death and one who personally revels in another human’s suffering.
Yes, Putin is evil for ordering torture or assassination. But he’d be far more evil if he took pleasure in doing it himself. That’s the purest form of darkness... not the bureaucrat of death, but the one who feeds on pain.
That’s what O’Reilly’s book never fully captures. Confronting Evil succeeds as moral storytelling, but not as moral philosophy. It raises big questions about good and evil but doesn’t wrestle with them deeply enough. Still, it’s a powerful and fast read—and worth finishing if you want to think about what makes evil recognizable in every age, even when it wears different faces.
On a positive note, it was a great book... like most of O’Reilly’s. I flew through it. It’s engaging, thought-provoking, and written in that straightforward, no-nonsense style that makes his books so readable. I really enjoyed it... it’s interesting, informative, and kept me hooked from start to finish. Even when I disagreed with some of his conclusions, I appreciated how he made complex history feel alive and accessible.