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Sîn-šar-iškun (Neo-Assyrian Akkadian: 𒁹𒀭𒌍𒌋𒌋𒃻𒌦, romanized: Sîn-šar-iškun or Sîn-šarru-iškun, meaning "Sîn has established the king") was the penultimate king of the Neo-Assyrian Empire, reigning from the death of his brother and predecessor Aššur-etil-ilāni in 627 BCE to his own death at the Fall of Nineveh in 612 BCE.
Succeeding his brother in uncertain, possibly violent circumstances, Sîn-šar-iškun was immediately faced by the revolt of one of his brother's chief generals, Sîn-šumu-līšir, who attempted to usurp the throne for himself and briefly took over much of Babylonia. Though Sîn-šumu-līšir was defeated relatively quickly, the instability caused by his revolt, combined with an ongoing interregnum in Babylonia in the south (neither Sîn-šar-iškun nor Sîn-šumu-līšir had formally proclaimed themselves as kings of Babylon) might be what made it possible for Nabopolassar, a southerner of unclear origin, to rise up and seize power in Babylonia. Sîn-šar-iškun's inability to defeat Nabopolassar, despite repeated attempts over the course of several years, allowed Nabopolassar to consolidate power and form the Neo-Babylonian Empire, restoring Babylonian independence after more than a century of Assyrian rule and centuries of domination prior to that.
The Neo-Babylonian Empire, and the Median ruler Cyaxares, technically still a vassal of Assyria, then invaded the Assyrian heartland. In 614 BCE, the Medes captured and sacked Assur, the ceremonial and religious heart of the Assyrian Empire while much of the Assyrian army was occupied fighting the Babylonians, and in 612 BCE their combined armies attacked, brutally sacked, and razed Nineveh, the Assyrian capital. Sîn-šar-iškun's fate is unknown, but it is assumed that he died in the defence of his capital. He was succeeded as king only by Aššur-uballiṭ II, possibly his son, who fought his way out of Nineveh and rallied what remained of the Assyrian army at the city of Harran
Despite the catastrophic fall of Assyria during his time as king, there is nothing to suggest that Sîn-šar-iškun was any less competent than his successful warrior-king predecessors who had dominated Western Asia for centuries. He employed the same tactics as his predecessors and appears to have utilized his forces rationally and strategically, fighting entirely in-line with traditional Assyrian warfare. What doomed the Assyrian Empire might instead have been a combination of the weakening of Assyrian military power caused by internal revolts, the lack of an effective defensive plan for the Assyrian heartland, which had not been successfully invaded in over eight hundred years, over expansion of the Assyrian empire leading its military to be spread too thinly, combined with having to face multiple enemies in large numbers which aimed to outright destroy Assyria rather than simply conquer it.

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