It’s not just the “benevolent dictator” that’s at question — it’s everyone else in the system, from the military to the civil service. Even with the most benevolent dictator, greedy civil servants could cripple the goodwill of any dictator with massive corruption; on the same hand, a “too generous” dictator could be taken down by jealous generals or restless colonels.

A “benevolent dictatorship” only works with everyone is on-board for the betterment of the country. This is why, IMHO, it can only work with an overriding factor that transcends society, such as nationalism. Of course there is plenty of danger of overindulgence in nationalism, as we’ve seen in the past.

If you look at Estonia in the 1930s, where there was a so-called “benevolent dictatorship” under Konstantin Päts, it worked rather well. Despite the lack of true democracy, the crackdowns were mild compared to the rest of Europe. Plus, the “guided democracy” that they installed helped the country to develop its economy after the Great Depression to a point where their economic development was in the same range as Finland and other Nordic countries.

Of course Stalin and Hitler put an end to all that. Who knows how well that “benevolent dictatorship” would have turned out if external factors (WWII and occupations) did not disrupt it. Would it have collapsed or transitioned successfully?

Good question tho…