Son of Josiah and king of Judah for eleven years, at a time when the entire region was thrown into upheaval by the swift rise to power of the Babylonians immediately after they had brought an end to the Assyrian empire. He was a particular grief to Jeremiah and Scriptures—not even the generally rather forgiving Chronicler—have nothing good to say about him. The reports of Jehoiakim's reign in Kings and Chronicles are very brief (for all of his eleven years reign, he warranted only 9½ verses in Kings and 5 in Chronicles); to understand him as a king and person, one should rather turn to the book of Jeremiah (of the 37x his name appears in the Bible, it appears only 15x outside of Jeremiah).
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609 BC, when Jehoiakim began his reign, was a tumultuous year for everyone living in the Ancient Near East. In the far north the Babylonians—fast rising to become the new superpower—had cornered the Assyrians in Haran, where they were making their last stand. Egypt marched north hoping to shore up the Assyrians; if she could keep even a greatly diminished Assyria alive in the north she would also keep the Babylonians occupied and out of the south. On the way she met Josiah in battle at Megiddo; Josiah was killed. The Egyptians, however, arrived too late to do the Assyrians any good; they had been defeated and there was nothing but for the Pharaoh, Neco, to return home. When they came back to Judah they found, quite naturally, Jehoahaz, Josiah's elder son, enthroned in his father's place. To show the Jews who was now boss over them, they took Jehoahaz prisoner, and make his twenty-five-year-old half-brother, Eliakim, king instead. In a further act of imperial humiliation, they changed his name to Jehoikim and force Judah to pay a huge tribute in gold and silver (2 Ki 23:35).
Once the Babylonians, now under the leadership of Nebuchadnezzar, had consolidated their power in the north, they marched south. Jehoiakim, in his fourth year as king, was made a Babylonian vassal (2 Ki 24:4; Jer 25:1), and treasures from the temple and some of the best men in the country were removed to serve the king in Babylon (Dan 1:1-2). During all his eleven year reign Jehoiakim would have Jeremiah hounding his back for his godless leadership of Judah, and he and his officials, in turn, would made life a hell for the young prophet—cutting up a scroll Jeremiah had dictated strip after strip after he had read them and burning them in the fire (Jer 36) and threatening of his life (Jer 26:1-11). But given the pro-Egyptian leanings of his court, Jehoiakim could never remain a faithful vassal of Babylon, and within a few short years he rebelled. Occupied with other priorities, Babylon was for a while just happy to harass Judah with allied forces ("the Lord sent . . . Aramean, Moabite and Ammonite raiders against him. He sent them to destroy Judah, in accordance with the word of the Lord proclaimed by his servants the prophets" (2 Ki 24:2), but by late 598 BC, the main Babylonian army was before Jerusalem's gate. What exactly happened next is unclear. Jehoaikim seemed to have died before their arrival, possibly executed by his own official in the hope of a lighter reprisal. The hoped for aid from the Egyptians never materialized ("The king of Egypt did not march out from his own country again, because the king of Babylon had taken all his territory, from the Wadi of Egypt to the Euphrates River." 2 Ki 24:7.) In any case, when the city surrendered on 15/16 March the following year, the Babylonians found his son, Jehoiachin on the throne. Nebuchadnezzar did respond rather leniently; Jehoiachin and a significant number of officials (including Ezekiel) were taken hostage to Babylon (often referred to as the First Deportation), and Jehoiachin's uncle, Zedekiah was made king instead. Judah had gotten off lightly. The next deportation would empty Judah.
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