The Atlantic
Autocrats such as Putin eventually succumb to what may be called the “dictator trap.” The strategies they use to stay in power tend to trigger their eventual downfall. Rather than being long-term planners, many make catastrophic short-term errors—the kinds of errors that would likely have been avoided in democratic systems. They hear only from sycophants, and get bad advice. They misunderstand their population. They don’t see threats coming until it’s too late. And unlike elected leaders who leave office to riches, book tours, and the glitzy lifestyle of a statesman, many dictators who miscalculate leave office in a casket, a possibility that makes them even more likely to double down.
Despots sow the seeds of their own demise early on, when they first face the trade-off between allowing freedom of expression and maintaining an iron grip on power. After arriving in the palace, crushing dissent and jailing opponents is often rational, from the perspective of a dictator: It creates a culture of fear that is useful for establishing and maintaining control. But that culture of fear comes with a cost.
For those of us living in liberal democracies, criticizing the boss is risky, but we’re not going to be shipped off to a gulag or watch our family get tortured. In authoritarian regimes, those all-too-real risks have a way of focusing the mind. Is it ever worthwhile for authoritarian advisers to speak truth to power?
As a result, despots rarely get told that their stupid ideas are stupid, or that their ill-conceived wars are likely to be catastrophic. Offering honest criticism is a deadly game and most advisers avoid doing so. Those who dare to gamble eventually lose and are purged. So over time, the advisers who remain are usually yes-men who act like bobbleheads, nodding along when the despot outlines some crackpot scheme.