King of Judah (608-597
Although Jehoiakim was Josiah's eldest son, he was passed over at the latter's death as being unworthy to be his father's successor, and his brother Jehoahaz mounted the throne in his place. Jehoahaz was publicly anointed king to offset his brother's claims to the throne (Seder 'Olam R. xxiv.; Hor. 11b; Ratner's objection ad loc. to Seder 'Olam was anticipated and answered by the Gemara). When, subsequently, Jehoiakim took the government, after Jehoahaz had been led captive to Egypt, he showed how little he resembled his pious father: he was a godless tyrant, committing the most atrocious sins and crimes. He lived in incestuous relations with his mother, daughter-in-law, and stepmother, and was in the habit of murdering men, whose wives he then violated and whose property he seized. His garments were of "sha'aṭneẓ," and in order to hide the fact that he was a Jew, he had made himself an epispasm by means of an operation, and had tattooed his body (Lev. R. xix. 6; Tan., Lek Leka, end; Midr. Aggadat Bereshit xlviii.; see also Sanh. 103b). He even boasted of his godlessness, saying, "My predecessors, Manasseh and Amon, did not know how they could make God most angry. But I speak openly; all that God gives us is light, and this we no longer need, since we have a kind of gold that shines just like the light; furthermore, God has given this gold to mankind [Ps. cxv. 16] and is not able to take it back again" (Sanh. l.c.).
When Jehoiakim was informed that Jeremiah was writing his Lamentations, he sent for the roll, and calmly read the first four verses, remarking sarcastically, "I still am king." When he came to the fifth verse and saw the words, "For the Lord hath afflicted her for the multitude of her transgressions" (Lam. i. 5), he took the roll, scratched out the names of God occurring therein, and threw it into the fire (M. Ḳ. 26a). No wonder then that God thought of "changing the world again into chaos," and refrained from doing so only because the Jewish people under this king were pious (Sanh. 103a). Yet punishment was not withheld. Nebuchadnezzar came with his army to Daphne, near Antiochia, and demanded from the Great Sanhedrin, whose members came to pay him their respects, that Jehoiakim be delivered to him, in which case he would not disturb the city and its inhabitants. The Sanhedrin went to Jehoiakim to inform him of Nebuchadnezzar's demand, and when he asked them whether it would be right to sacrifice him for their benefit, they reminded him of what David did in a similar case with the rebel Sheba (Lev. R. xix. 6).
Various opinions have been handed down concerning the circumstances of Jehoiakim's death, due to the difficulty of harmonizing the conflicting Biblical statements on this point (II Kings xxiv. 6; Jer. xxii. 18, 19; II Chron. xxxvi. 6). According to some, he died in Jerusalem before the Sanhedrin could comply with the demand made by Nebuchadnezzar, who therefore had to be content with the king's body, which was cast to him over the walls. Another version says that he died while being let down over the wall. Others, again, maintain that after leading him through the whole land of Judah, Nebuchadnezzar killed him, and then threw his corpse piecemeal to the dogs, or, as one version has it, put it into the skin of a dead ass (Lev. R. xix. 6; Seder'Olam R. xxv., agreeing in part with Josephus, "Ant." x. 6, § 3; see also Jerome to Jer. xxii. 18, and Nebuchadnezzar in Rabbinical Literature).
Even this shameful death, however, was not to be the end of the dead king, upon whose skull were scratched the words, "This and one more." After many centuries the skull was found by a scholar before the gates of Jerusalem; he piously buried it, but as often as he tried to cover it the earth refused to hold it. He then concluded that it was the skull of Jehoiakim, for whom Jeremiah had prophesied such an end (Jer. xxii. 18); and as he did not know what to do with it, he wrapped it in a cloth and hid it in a closet. After a time his wife found it and showed it to a neighbor, who said: "Your husband had another wife before you whom he can not forget, and therefore he keeps her skull." Thereupon the wife threw it into the fire, and when her husband returned he knew what the enigmatical words "this and one more" meant (Sanh. 82a, 104a). Notwithstanding his many sins, Jehoiakim is not one of the kings who have no part in the future world (Sanh. 103b).