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Coolest historical leader?
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If we’re going for “cool story” rather than “admirable person”, then the Byzantine emperor Justinian II.
Tell us a story!
After ruling for ten years he was overthrown, had his nose cut off, and was exiled to the Crimea. Suspected of conspiring to return to power, he was summoned back to Constantinople for additional punishment; but instead he escaped to the Russian steppe where he married the sister of the Khazar kaghan. The usurpers bribed the kaghan to extradite his new brother-in-law back to the Byzantines, but Justinian was warned by his Khazar wife and killed the kaghan’s officials sent to arrest him. Then he escaped in a fishing boat to the Balkans, married his daughter to the Bulgar khan, and convinced the khan to lend him an army to defeat the usurpers. So after a ten-year exile he returned to Constantinople at the head of a barbarian army, but the city refused to surrender. Finally he used his knowledge of the city’s infrastructure to crawl in through the sewers, re-took the palace by surprise, and ruled another six years before being killed in a second rebellion.
Holy crap, that is wild. I'm going into a rabbit hole about him, this is great!