I'm not sure Singapore's government falls under a military dictatorship by any means.
But hey, I said what had to be said, and see no point arguing about the formalities. I'll let HN users decide for themselves.
That actually weakens the claim that it's a military dictatorship. If the army is controlled by civilians, its not a military dictatorship. If a person becomes leader of the military due to civilian connections, then it's not a military dictatorship.
A military dictatorship is when a person becomes civilian leader by virtue of their military leadership. If the son of the civilian prime minister first gets to take over the army, it doesn't change the fact that he's fundamentally a civilian and the civilians are controlling - inside and out - the military. It reinforces it. He led the army and the country because of his civilian credentials.
This sounds more like rule by and for a family or a small group of elites.
According to this logic, the United States was a military dictatorship for a good portion of its history. Presidents Washington, Jackson, W. Harrison, Taylor, Pierce, A. Johnson, Grant, Hayes, Garfield, Arthur, B. Harrison, and Eisenhower were all generals. Your claim is absurd.
A military dictatorship installs the dictator and the dictator relies on the support the generals to stay in power.
That isn't the case in Singapore (nor many other dictatorships, where the dictator controls the military).
You can tell by if the dictator has generals replaced, or vice-versa.
https://en.wikipedia.org/wiki/List_of_regimes
Not seeking to discredit the ruling party. What they've done with Singapore is nothing short of a miracle. But the fact is that they're still backed up by a ridiculously strong army, and the opposition party exists just so they can say there is one (but is frequently bullied regardless).
Note that by this measure, there can be "military democracies", such as the U.S. during 55 years (in 1946-2008) where the president was ex-military (e.g. Bush).
[0] https://sites.google.com/site/joseantoniocheibub/datasets/de...
The Singapore government has been trying to move away from this — a significant part by requesting that the press address them as "Mr", instead of their military ranks. There was a time when Lee Hsien Loong was addressed as `BG (NS) Lee Hsien Loong` everywhere [1].
One of the potential heirs to the Prime Ministership is the ex-Chief of Army, Chan Chun Sing [2]. It's very rare to see either the media, or the government themselves, to address him as `MG (NS) Chan Chun Sing` in their publications.
[1] Example from a government website: https://www.nas.gov.sg/archivesonline/speeches/record-detail...