When leaders demand total loyalty and surround themselves with flatterers, disaster follows. Every time. It’s not a question of if—it’s a question of when. From emperors to kings to dictators to presidents, history makes one thing clear: when sycophancy takes over, collapse is right behind it. And if you think the United States is immune, take a hard look at what’s happening right now.
The Roman emperors Caligula, Nero, and Commodus demanded worship instead of wisdom, ignored all bad news, and were assassinated by their own people. In Renaissance Europe, kings who listened only to their sycophantic courts—Henry III of France, Charles I of England—ended up overthrown, exiled, or executed. In the 20th century, authoritarian rulers from Hitler to Ceaușescu built loyalty cults so airtight that when reality finally broke through, their regimes collapsed almost overnight. The through-line? Leaders who surrounded themselves with yes-men became detached from reality, made catastrophic decisions, and lost the support of the very people keeping them in power.
The same dynamic plays out in the corporate world. Enron, Theranos, WeWork—massive, billion-dollar companies brought down not just by fraud but by leaders who refused to hear the truth. They built cultures where questioning the boss meant exile, so no one spoke up when disaster was looming. It’s the same disease that kills governments: a leader so insulated by praise that they steer straight off the cliff, cheered on the whole way.
And now? We are watching this cycle unfold in real time. When truth is punished, when flattery is rewarded, when blind loyalty is the price of power—failure is inevitable. History is clear: when sycophancy runs a government, it won’t run for long.
Coda
It wasn't the Trump / Zelensky meeting, it was the republican response that put an arrow in my optimism.
I'd been wanting to try out GPT's Deep Research function and yesterday I fed it this prompt:
“So, I'm watching the Trump presidency and something's really, really nagging me and it's the requirement for sycophancy. It's the requirement for obsequiousness. Watching Zelensky in with Trump and everybody, the right wing, are saying, well, you've just got to butter him up, you've got to be nice to him, you've got to flatter him. And that's the thing that's doing my head in, because it just feels wrong. It feels absolutely wrong, and I have a gut feel and intuition that if we look at history, that there are times in history when, where sycophancy was required by the prince, by the leader, what happens?
My gut feels is it has to fail. What I'm looking for is deep research across history, across recorded human history, of when strong princes arrive, and leaders and, you know, whatever, executives. We can see this in the business world too, where they created this culture of ego where the leader needed to be flattered, where you needed to become an expert in sycophancy, in obsequiousness, in order to get what you want.
I want to know what the implications of that are, and does it match my hypothesis that a requirement for sycophancy in a political structure or a business structure is ultimately a road to ruin.”
This post is the tl;dr - read the well researched and well put together essay here.
