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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 Assyria, reigning from the death of his brother and predecessor Aššur-etil-ilāni in 627 BC to his own death at the Fall of Nineveh in 612 BC.

Succeeding his brother in uncertain, but not necessarily 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. 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.

The Neo-Babylonian Empire, and the newly formed Median Empire under Cyaxares, then invaded the Assyrian heartland. In 614 BC, the Medes captured and sacked Assur, the ceremonial and religious heart of the Assyrian Empire, and in 612 BC 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 defense of his capital. He was succeeded as king only by Aššur-uballiṭ II, possibly his son, who 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. 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 Assyria might instead have been the lack of an effective defensive plan for the Assyrian heartland, which had not been invaded in five hundred years, combined with having to face an enemy which aimed to outright destroy Assyria rather than simply conquer it.

As a consequence of Assyria's violent downfall, the period from a few years before the death of Ashurbanipal to the Fall of Nineveh in 612 BC suffers from a distinct lack of surviving sources. The annals of Ashurbanipal, the primary sources for his reign, go no further than 636 BC. Although Ashurbanipal's final year is often repeated as 627 BC, this follows an inscription at Harran made by the mother of the Neo-Babylonian king Nabonidus nearly a century later. The final contemporary evidence for Ashurbanipal being alive and reigning as king is a contract from the city of Nippur made in 631 BC. To get the attested lengths of the reigns of his successors to match, most scholars agree that Ashurbanipal either died, abdicated or was deposed in 631 BC. Of the three options, a death in 631 BC is the most accepted. If Ashurbanipal's reign would have ended in 627 BC, the inscriptions of his successors Aššur-etil-ilāni and Sîn-šar-iškun in Babylon, covering several years, would have been impossible since the city was seized by the Neo-Babylonian king Nabopolassar in 626 BC to never again fall into Assyrian hands.

Ashurbanipal had named his successor as early as 660 BC, when documents referencing a crown prince (probably Aššur-etil-ilāni) were written. He had been the father of at least one son, and probably two, early on in his reign. These early sons were likely Aššur-etil-ilāni and Sîn-šar-iškun. Aššur-etil-ilāni succeeded Ashurbanipal as king in 631 BC and ruled until his own death in 627 BC. It is frequently assumed, without any supporting evidence, that Sîn-šar-iškun fought with Aššur-etil-ilāni for the throne.

Sîn-šar-iškun has sometimes historically and erroneously been known as Esarhaddon II after a letter written by Šērūʾa-ēṭirat, a daughter of Sîn-šar-iškun's grandfather Esarhaddon. The chronology and relations of the royal family were uncertain and Šērūʾa-ēṭirat was believed to have been too young to refer to the famous Esarhaddon. The idea of a separate Esarhaddon II as king has been abandoned by Assyriologists since the late 19th century, but the name sometimes appears as a synonym of Sîn-šar-iškun.

In the middle of the seventh century BC, the Neo-Assyrian Empire ruled the entire Near East. Due to their powerful standing army and their sophisticated administration, the Assyrians had managed to create the best organized and largest empire that the world had yet seen. Though Babylonia in the south had also once been a large kingdom, it had typically been weaker than its northern neighbor due to internal divisions and the lack of a well-organized army. The population of Babylonia was divided into various ethnic groups with different priorities and ideals. Though old native Babylonians ruled most of the cities, such as Kish, Ur, Uruk, Borsippa, Nippur, and Babylon itself, the Chaldean tribes, led by chieftains who often squabbled with each other, dominated most of the southernmost land. The Arameans lived on the fringes of settled land and were notorious for plundering surrounding territories. Because of the infighting of these three major groups, Babylonia often represented an appealing target for Assyrian campaigns. The two kingdoms had competed since the rise of the Middle Assyrian Empire in the 14th century BC, and in the 8th century BC, the Assyrians consistently gained the upper hand. Babylon's internal and external weakness led to its conquest by the Assyrian king Tiglath-Pileser III in 729 BC.

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