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Jeremiah 39:1 It happened when Jerusalem was taken, (in the ninth year of Zedekiah king of Judah, in the tenth month, came Nebuchadnezzar king of Babylon and all his army against Jerusalem, and besieged it- The exacter date is given in Jer. 52:4-7, meaning that the siege lasted exactly 18 months.

Jeremiah 39:2 in the eleventh year of Zedekiah, in the fourth month, the ninth day of the month, a breach was made in the city)-
The Babylonians made a breach in the wall to the north, from where the cherubim had left and would return. But Zedekiah tried to escape by digging a hole in the southern wall (Ez. 12:12). He did to the city what the Babylonians did, living out his own condemnation; see on :7. This "breach" is the same word used for the breaking up of things at the time of the flood (Gen. 6:11), a well established foretaste of the destruction of Jerusalem by the flood waters of the Babylonians, albeit with the promise of a new creation coming as a result of it.

Jeremiah 39:3 that all the princes of the king of Babylon came in, and sat in the middle gate-
The gate separating the citadel of Zion where the temple was, from the rest of Jerusalem. In other words, the temple was about to be taken.

Nergal Sharezer, Samgarnebo, Sarsechim, Rabsaris, Nergal Sharezer, Rabmag, with all the rest of the princes of the king of Babylon- These are titles rather than personal names. Many of them are plays on the names of their gods, such as Nebo. Rabmag was the master of the magi, and the idea was that the gods of Babylon had triumphed over Jerusalem.

Jeremiah 39:4 It happened that when Zedekiah the king of Judah and all the men of war saw them, then they fled and went forth out of the city by night, by the way of the king’s garden, through the gate between the two walls-
It seems Zedekiah had taken refuge in the temple. From there, he saw the princes of Babylon who had breached the northern wall and were now at the temple gate (:3). And so they fled by "the king's garden", which was his own private entrance to the temple, and then came to the double walls of the southern perimeter of the city. Zedekiah himself dug through those walls, the strongest point of his defence and human strength (Ez. 12:12). He was being taught that all human defence, and the physical temple, was not going to save him.

And he went out towards the Arabah- "Went out" is the language of Judas going out (Jn. 13:30), Cain '"went out" (Gen. 4:16), as did Zedekiah in the judgment of Jerusalem (Jer. 39:4; 52:7). Esau went out from the land of Canaan into Edom, slinking away from the face of his brother Jacob, sensing his righteousness and his own carnality (Gen. 36:2-8). Even in this life, those who leave the ecclesia 'go out' after the pattern of Judas, condemning themselves in advance of the judgment by their attitude to the ecclesia (1 Jn. 2:19 cp. Acts 15:24). The unrighteous flee from God now, as they will then (Hos. 7:13).

Jeremiah 39:5 But the army of the Chaldeans pursued after them, and overtook Zedekiah in the plains of Jericho: and when they had taken him, they brought him up to Nebuchadnezzar king of Babylon to Riblah in the land of Hamath-
The main lying helpless on the Jerusalem - Jericho road was surely modeled on Zedekiah being overtaken there by his enemies. That weak, vacillating man basically loved God's word, he wanted to be obedient, but just couldn't bring himself to do it. And so he was, quite justly, condemned. It's as if the Lord saw in that wretched, pathetic man a type of all those He came to save. And even in this wretched position, the Lord will pick us up and carry us home. Pursuing and overtaking are the words used of the punishment to come upon those who broke the covenant (Dt. 28:45).

And he gave judgment on him- He 'spoke judgments', as if Zedekiah were a common criminal no longer protected by his royal status. 2 Kings 25:5 adds the detail that his army was scattered from him; he was left alone to face judgment. This was God's intention; to make Zedekiah face judgment alone, so that he might be the more in touch with his God and repent. For this is one function of the loneliness which God brings.

Jeremiah 39:6 Then the king of Babylon killed the sons of Zedekiah in Riblah before his eyes: also the king of Babylon killed all the nobles of Judah-
The princes were killed, but Zedekiah was spared. He had been given a wonderful opportunity to repent in Jer. 38, but had spurned it. And yet he was still spared the loss of his life, although he had been told he would lose his life (Jer. 38:17). Presumably his deep repentance as he faced his condemnation was so impressive that God spared his life; whereas the princes didn't repent.

Jeremiah 39:7 Moreover he put out Zedekiah’s eyes, and bound him in fetters to carry him to Babylon-
This is how Jeremiah saw Nebuchadnezzar's eyes (Jer. 34:3) and yet came to Babylon without seeing it (Ez. 12:13). Zedekiah fled Jerusalem disguised as a woman with his face so bound around with some disguise that he couldn't see (Ez. 12:12). He was living out his own condemnation, which was to be blinded. See on :2.

Jeremiah 39:8 The Chaldeans burned the king’s house and the houses of the people with fire, and broke down the walls of Jerusalem-
Israel were told to "throw down", "break in pieces" and "utterly destroy" the idols and altars of Canaan. There were times during their history when they obeyed this command by purging themselves from their apostasy in this. The Hebrew words used scarcely occur elsewhere, except very frequently in the context of how God "broke down", "threw down" and "destroyed" Israel at the hands of their Babylonian and Assyrian invaders as a result of their not 'breaking down' (etc.) the idols. "Throw down" in Ex. 34:13; Dt. 7:5; 12:3; 2 Chron. 31:1 is the same word in 2 Chron. 36:19; Jer. 4:26; 31:28; 33:4; 39:8; 52:14; Ez. 16:39; Nah. 1:6. "Cut down" in Dt. 7:5; 12:3; 2 Chron. 31:1 later occurs in Is. 10:33; Jer. 48;25; Lam. 2:3. So Israel faced the choice: either cut down your idols, or you will be cut down in the day of God's judgment. Those who worshipped idols were like unto them. The stone will either fall on us and destroy us, or we must fall on it and become broken men and women (Mt. 21:44). For the man untouched by the concept of living for God's glory, it's a hard choice.

Jeremiah 39:9 Then Nebuzaradan the captain of the guard carried away captive into Babylon the remnant of the people who remained in the city, the deserters also who fell away to him, and the residue of the people who remained-
The "remnant" is the remainder of those who had not died from the sword, famine or plague. But there was a large element of "the poor of the people" (:10) who remained.

Jeremiah 39:10 But Nebuzaradan the captain of the guard left of the poor of the people, who had nothing, in the land of Judah, and gave them vineyards and fields at the same time-
The majority of the population remained, because they were those who had nothing and were abused by the wealthy minority; and they received their vineyards and fields. They did well out of the Babylonian invasion; and that was Babylonian policy, to deport only the leadership and ingratiate themselves to the poor masses, in the hope they would thereby have their loyalty.

It needs to be noted that poverty has a way of distracting, terribly so. Merely giving aid to the poor won't automatically make converts- true converts. It’s simply not true that desperately poor people will somehow respond better than others to the Gospel. The Jews left in the land at the time of the exile were the very poorest. But actually these were the spiritually weaker in the long run, and it was the more wealthy who went to Babylon who were the “good figs” of Jer. 24:3-8.

Jeremiah 39:11 Now Nebuchadnezzar king of Babylon commanded Nebuzaradan the captain of the guard concerning Jeremiah saying-
Nebuchadnezzar was then at Hamath, Antioch on the Orontes. He would have heard about Jeremiah from the Jews who had already defected in response to Jeremiah's prophecies, and they would have told him of Jeremiah's prophecies; which was why he was well disposed toward Jeremiah, perhaps ignorant of or choosing to ignore the other prophecies about Babylon's destruction.

Jeremiah 39:12 Take him, and look well to him, and do him no harm; but do to him even as he shall tell you-
'To set the eyes upon for good' (Heb.), "take care of" or "look well unto", could mean that God's eyes, the Angels, would bless the "good figs" in captivity and lead them to repentance and salvation. For that is the ultimate "good" which God plans for His people. But twice we read that Jeremiah could have gone into captivity and been looked upon for good (Jer. 39:12; 40:4 s.w. "I will set My eyes on them for good" in Jer. 24:6). Yet Jeremiah declined; he chose to suffer affliction with the condemned, with the bad figs of the Jer. 24 prophecy, so that he might still help them to repentance. This looked forward to the Lord's death as a sinner on the cross. And it is to be our spirit too, ever seeking the repentance of those who otherwise will be condemned rather than enjoying time solely with those who apparently will be saved.

Jeremiah 39:13 So Nebuzaradan the captain of the guard sent, and Nebushazban, Rabsaris, Nergal Sharezer, Rabmag, and all the chief officers of the king of Babylon-
The top brass of Babylon were all involved in this singular mission- to locate and do well to this individual called Jeremiah. Such was God's deep desire to reward and care for Jeremiah.

Jeremiah 39:14 they sent, and took Jeremiah out of the court of the guard, and committed him to Gedaliah the son of Ahikam, the son of Shaphan, that he should carry him home: so he lived among the people-
But initially Jeremiah was taken captive in chains (Jer. 40:1), perhaps in the confusion which arose after the sacking of Jerusalem. He was released from those chains and given the best treatment, given a place in the house of Gedaliah whom the Babylonians had appointed governor. But Jeremiah had a heart for people, wanting only to minister God's word to them. Even that relatively luxurious position is described according to how Jeremiah perceived it- he lived "among the people". And this of course is an example to us, wherever our lot be cast.

Jeremiah 39:15 Now the word of Yahweh came to Jeremiah, while he was shut up in the court of the guard, saying-
This is the word that had come to Jeremiah previously. The book of Jeremiah isn't chronological, but arranged by theme. Here the theme is that God wonderfully preserved Jeremiah because of his faithfulness; and He did the same for Ebedmelech.

Jeremiah 39:16 Go and speak to Ebedmelech the Ethiopian saying, Thus says Yahweh of Armies, the God of Israel: Behold, I will bring My words on this city for evil, and not for good; and they shall be accomplished before you in that day-
Jeremiah was "shut up" in prison (:15); so 'going' is used in the figurative sense, as a metaphor to describe taking the Gospel to someone, even if we are confined to our bed. See more examples of this noted on 1 Pet. 3:19.

Jeremiah 39:17 But I will deliver you in that day, says Yahweh; and you shall not be given into the hand of the men of whom you are afraid-
To march into the prison with 30 men and rescue Jeremiah from the dungeon of death was nothing less than staging a jail break. Ebedmelech showed huge faith and devotion in doing this, and naturally feared for his life afterwards. His deliverance from the Jews was to encourage him that like Jeremiah, his life would be saved from the Babylonians too. "You shall not be given..." is just what Zedekiah had been encouraged- if he had repented (Jer. 38:20). He likewise was "afraid of... men", the same Jewish princes who were out to kill Ebedmelech. We see here the thematic nature of the book of Jeremiah. God worked in the same way in parallel lives, and some accepted His promises and others didn't.

Jeremiah 39:18 For I will surely save you, and you shall not fall by the sword, but your life shall be for a prey to you; because you have put your trust in me, says Yahweh
- His life would be to him "for a prey", literally, as booty taken from a conquered city. This was and is the great paradox- that surrender, acceptance of defeat, was the great spiritual victory. LXX "and you shall find your life" is alluded to in the Lord's promise that he who loses his life [or risks losing it] for the Lord's sake shall find it (Mt. 10:39; 16:25). The reward for Ebedmelech was not just that he would save his physical life, but that he would find his true life. He thereby stands representative of us all.