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Fausset's Bible Dictionary
1. Judah's last king, 599 to 588 B.C. (See .) Youngest son of Josiah and Hamutal (Jeremiah 1:3; Jeremiah 37:1), brother to Jehoahaz (2 Kings 24:17-18; 2 Kings 23:31). Ten years old when his father died, 21 when he mounted the throne. Originally named Mattaniah; Nebuchadnezzar changed his name to Zedekiah when he deposed Zedekiah's nephew Jehoiachin. This proves that Nebuchadnezzar treated his vassal kindly, allowing him to choose a new name (Zedekiah is Hebrew, "righteousness of Jehovah") and confirming it as a mark of his supremacy; this name was to be the pledge of his righteously keeping his covenant with Nebuchadnezzar who made him swear by God (Ezekiel 17:12-16; 2 Chronicles 36:13).
In 1 Chronicles 3:15 Johanan is oldest, then Jehoiakim, Zedekiah is third in order, Shallum fourth, because Jehoiakim and Zedekiah reigned longer, namely, 11 years each; therefore Shallum, though king before Jehoiakim, is put last; on the other hand Zedekiah and Shallum were both sons of Hamutal, therefore put together. Had Zedekiah kept his oath of fealty he would have been safe, though dependent. But weak, vacillating, and treacherous, he brought ruin on his country and on himself. It was through the anger of Jehovah against Judah that Zedekiah was given up to his own rebellious devices, "stiffening his neck and hardening his heart from turning unto the Lord God of Israel" who warned him by Jeremiah; like Pharaoh of old (2 Chronicles 36:12-13), he would "not humble himself" (Jeremiah 38:5; Jeremiah 39:1-7; Jeremiah 52:1-11; and Jeremiah 21; 24; 27; 28; 29; 32; 33; 34; 37; 38).
In Jeremiah 27:1 read "Zedekiah" for "Jehoiakim" with Syriac, Arabic, and one of Kennicott's manuscripts (compare Jeremiah 27:3; Jeremiah 27:12; and Jeremiah 28:1, "in the fourth year ... of the reign of Zedekiah") The kings of Edom, Moab, Ammon, Tyre, and Sidon sent ambassadors in his fourth year to urge Zedekiah to conspire with them against Nebuchadnezzar. But Jeremiah symbolized the futility of the attempt by sending "yokes" back by the ambassadors. Hananiah, who broke the yoke off Jeremiah's neck, died that year according to the Lord's sentence by Jeremiah. Baruch (Baruch 1:8) represents Zedekiah as having caused silver vessels to be made to replace the golden ones carried off by Nebuchadnezzar; possibly this may have been owing to the impression made on Zedekiah by Hananiah's death.
In his eighth year (Josephus Ant. 10:7, Section 3) Zedekiah actually leagued with Egypt in treacherous violation of his compact with Nebuchadnezzar. But evidently (Jeremiah 27-28) Zedekiah had been secretly plotting before, in his fourth year; in that year he had gone to Babylon to allay Nebuchadnezzar's suspicion (Jeremiah 51:59), and also sent messengers to Babylon (Jeremiah 37:5-11; Jeremiah 34:21; Ezekiel 17:13-20). Zedekiah disregarded Jehovah's words by Jeremiah, notwithstanding the warning given in Jeconiah's punishment. Still while the issue between the Chaldaeans and Pharaoh Hophra was undecided, he sent begging Jeremiah, Pray now unto the Lord our God for us.
Nebuchadnezzar on learning Zedekiah's treachery had sent a Chaldaean army which reduced all Judaea except Jerusalem, Lachish, and Azekah (Jeremiah 34). Zedekiah had in consequence induced the princes and people to manumit their Hebrew bond servants. But when Pharaoh Hophra compelled the Chaldaeans to raise the siege of Jerusalem, the princes and people in violation of the covenant enslaved their Hebrew servants again. So God by Jeremiah gave the enslavers a "liberty" (Jeremiah 34:17) fatal to them, manumission from God's free service (Psalms 119:45; John 8:36; 2 Corinthians 3:17), to pass under the bondage of the sword, pestilence, and famine.
Then followed Jeremiah's attempt to escape to his native place and his arrest. Zedekiah sent and took him out of prison, and asked, Is there any word from the Lord? to which the prophet, without regard to his personal interests, replied, "there is, for thou shalt be delivered into the hand of the king of Babylon." Zedekiah showed his sense of Jeremiah's faithfulness by ordering bread to be given him out of the bakers' street until all the bread in the city was spent (Proverbs 28:23; Psalms 37:19). However, in consequence of his prophesying death to those that remained in the city and life to those who should go forth to the Chaldaeans, who had returned to the siege in the tenth month of Zedekiah's ninth year (Jeremiah 52:4), Jeremiah was again imprisoned. Zedekiah was too weak to resist, but answered his princes "the king is not he that can do anything against you."
At Ebedmelech's intercession Zedekiah rescued him, and again consulted him. Again Jeremiah told him his only hope was in going forth to the Chaldaeans. But Zedekiah was afraid lest the Chaldaeans should give him up to Jewish deserters, who would treat him ignominiously. Jeremiah told him in reply that, by not going forth, he should bring burning upon the city, and upon himself the very evil he feared if he went forth, ignominious treatment from not only the deserters but the very women of the palace (Jeremiah 38). So afraid was Zedekiah of his princes that he imposed on Jeremiah a subterfuge, concealing the real purpose of his interview from the princes. The terrible concomitants of a siege soon followed (Jeremiah 38:9), so that mothers boiled and ate the flesh of their own infants (Lamentations 4:5; Lamentations 4:8; Lamentations 4:10) and the visage of their nobles was blacker than coal, their skin clave to their bones and became withered.
On the ninth day of the fourth month in the middle of July (Josephus) after a year and a half's siege (from the tenth month of the ninth year to the fourth month of the eleventh year of Zedekiah) about midnight a breach was made in the wall The Babylonian princes took their seats in state in the middle gate, between the upper and the lower city. Zedekiah fled in the opposite direction, namely, southwards, with muffled face to escape recognition, and like one digging through a wall to escape (Ezekiel 12:12; Ezekiel 12:6), between the two walls on the E. and W. sides of the Tyropoeon valley, by a street issuing at the gate above the royal gardens and the fountain of Siloam. Zedekiah was overtaken in the plains of Jericho. He was taken for judgment to Riblah at the upper end of Lebanon; there Nebuchadnezzar first killed his sons before his eyes, then caused the eyes of Zedekiah to be "dug out" (Jeremiah 39; Jeremiah 52:4-11).
Thus were fulfilled the seemingly inconsistent prophecies, "his eyes shall behold his eyes," Jeremiah 32:4, and Ezekiel 12:13 "he shall not see Babylon, though he shall die there." Zedekiah was put "in prison," literally, "the house of visitations" or "punishments," where there was penal work enforced on the prisoners, as grinding, from whence Septuagint reads "in the house of the mill." So Samson "did grind" (Judges 16:21). He probably died before Evil Merodach, successor of Nebuchadnezzar, treated kindly Jehoiachin in the 37th year of his captivity, 26 years after the fall of Jerusalem; for no mention is made of him (Jeremiah 52:31).
2. Son of Chenaanah. (See , son of Imlah). 1 Kings 22; 2 Chronicles 18. He is distinguished by Jehoshaphat ("is there not here besides a prophet of Jehovah, that we might inquire of him?") from Jehovah's prophets. Zedekiah therefore was one of the "400 prophets of the GROVES" , (Asheerah Ashtaroth) who apparently were not slain when Elijah slew the 450 prophets of Baal (1 Kings 18:19; 1 Kings 18:22; 1 Kings 18:24), or rather a prophet of the calves symbolizing "Jehovah," for they spoke in Jehovah's name (1 Kings 22:8). Compare as to his assumption of horns Amos 6:13. Josephus adds (Ant. 8:15, section 3) that Zedekiah denounced Micaiah as contradicting Elijah, who foretold that dogs should lick up Ahab's blood in the vineyard of Naboth of Jezreel; and defied Micaiah to wither the hand with which he smote his cheek, as the prophet from Judah had done to Jeroboam.
3. Son of Maaseiah, a false prophet in Babylon, among the captives with Jeconiah. Jeremiah (Jeremiah 29:21-22; Jeremiah 29:25) denounces him for adultery and lying prophecies, buoying up the captives with delusive promises of a speedy restoration. A proverbial formula of cursing should be taken up by all the captives, "Jehovah make thee like Zedekiah and like Ahab whom the king of Babylon roasted in the fire!" (Isaiah 65:15.) Brother of Zephaniah.
4. Son of Hananiah. One of the princes assembled in the scribes' chamber when Micaiah announced that Baruch had read Jeremiah's words to the people (Jeremiah 36:12). He was not much better than his father, who died by God's visitation (Jeremiah 28:10-17).
5. Son of Jeconiah (1 Chronicles 3:16).
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Fausset, Andrew R. Entry for 'Zedekiah'. Fausset's Bible Dictionary. https://www.studylight.org/dictionaries/eng/fbd/z/zedekiah.html. 1949.