NorthDakota
Grandson of Loomis
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The Soviets were successful in WW2, though that was a big coalition.Who was the last authoritarian to win a major military conflict? I honestly can't think of any since WWI. Part of the reason is that people don't want to fight for a despot and the way the military is organized is generally inefficient or corrupt.
Chairman Mao was successful in the Chinese Civil War, but thats a civil war - locked up the West in Korea as well. Stalemate?
Francisco Franco - same as above sans Korea moment.
Ho Chi Minh and North Vietnam?
All of those are kinda iffy.

