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Jeremiah 40:1 The word which came to Jeremiah from Yahweh- There is no prophetic revelation for some time in the passage, as the following historical summary was required to give context to it.

After Nebuzaradan the captain of the guard had let him go from Ramah, when he had taken him being bound in chains among all the captives of Jerusalem and Judah, who were carried away captive to Babylon- As explained on Jer. 39:14, initially Jeremiah was taken captive in chains, perhaps in the confusion which arose after the sacking of Jerusalem; despite the specific command of none less than Nebuchadnezzar to give him special care and honour. 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" (Jer. 39:14). And this of course is an example to us, wherever our lot be cast. Perhaps Jeremiah went through this brief experience of being bound in chains so that he, like the Lord Jesus, could experience the condemnation of his people despite being personally innocent.

Jeremiah 40:2 The captain of the guard took Jeremiah and said to him, Yahweh your God pronounced this evil on this place-
The captain knew this because Jeremiah's prophetic words had been published and were well known. This is to Jeremiah's credit; that he didn't just keep his unpopular message to himself.

Jeremiah 40:3 and Yahweh has brought it, and done according as He spoke: because you have sinned against Yahweh, and have not obeyed His voice, therefore this thing has come on you-
As noted on :2, Jeremiah's earlier words had been well distributed. We note that Nebuzaradan uses the covenant Name of Yahweh. As intended, the whole tragedy was used to magnify God's Name and word amongst the Gentiles. People at that time understood a tribal god as always defending his own city. But this man understood that Yahweh was not such a tribal god; He brought judgment against His own people because He had a moral agenda, and was deeply sensitive to sin against Him. At that time, the whole concept of sin as a felt offence against a deity was unheard of.   

Jeremiah 40:4 Now, behold, I release you this day from the chains which are on your hand-
Jeremiah was representative of Judah; they too could have been loosed from their chains if they had repented and adopted God's perspective as Jeremiah did. Jeremiah was to be their pattern.

If it seems good to you to come with me into Babylon, come, and I will take care of you; but if it seems bad to you to come with me into Babylon, don’t- '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.

Behold, all the land is before you; where it seems good and right to you to go, there go- This is the language of Israel entering the land (Dt. 3:18 etc.). Again, Jeremiah was the representative of Judah and the living example of what could have been, and what could yet be for them.

Jeremiah 40:5 If you remain, then return to Gedaliah the son of Ahikam, son of Shaphan, whom the king of Babylon appointed governor of the cities of Judah, and dwell with him among the people. Or go wherever you think it right to go. So the captain of the guard gave him an allowance of food and a present, and let him go-
We are sometimes given such great freedom of choice, in order that we might have a chance to search our motives and do that which we "think right". Jeremiah's response is a stellar example to us. He chose to suffer affliction with God's people rather than seek his own security and prosperity in Babylon. Sometimes there are no morally wrong choices before us; but what is required is the right motivation for the choices we make. To have gone to Babylon and worked on bringing about the fulfillment of the "good figs" prophecy would surely have been legitimate. Instead Jeremiah chose to remain with the condemned, the "evil figs" who would not respond... in the hope they would somehow respond. He chose to "dwell among the people".

Jeremiah 40:6 Then went Jeremiah to Gedaliah the son of Ahikam to Mizpah, and lived with him among the people who were left in the land-
It is repeatedly emphasized that Jeremiah "lived... among the people". Even though he lived in Gedaliah's house in relatively luxury, his living is described according to how Jeremiah perceived it- he lived "among the people" (also :1; Jer. 39:14). And this of course is an example to us, wherever our lot be cast.

Jeremiah 40:7 Now when all the captains of the forces who were in the fields, even they and their men, heard that the king of Babylon had made Gedaliah the son of Ahikam governor in the land, and had committed to him men, and women, and children, and of the poorest of the land, of those who were not carried away captive to Babylon-
The existence of surviving Jewish military units indicates that the total destruction of Judah as intimated in Jeremiah's earlier prophecies didn't totally come about. In wrath God remembered mercy; or perhaps the mediation and repentance of a minority led to Him ameliorating His judgments. That is a theme of all his prophecies.

Jeremiah 40:8 then they came to Gedaliah to Mizpah, Ishmael the son of Nethaniah, Johanan and Jonathan the sons of Kareah, Seraiah the son of Tanhumeth, the sons of Ephai the Netophathite and Jezaniah the son of the Maacathite, they and their men-
Ishmael was later to murder Gedaliah, considering that he was the rightful king of Judah. It seems he had taken refuge with Baalis king of the Ammonites during the Babylonian invasion (:14).

Jeremiah 40:9 Gedaliah the son of Ahikam the son of Shaphan swore to them and to their men saying, Don’t be afraid to serve the Chaldeans: dwell in the land, and serve the king of Babylon-
Gedaliah was advocating the earlier appeal of Jeremiah; if the people accepted they had sinned and willingly accepted the judgment for it, servitude of their enemies, then all would be well for them. They were not to fear the Babylonians; the LXX and 2 Kings 25:24 say that they were not to fear “because of the servants of the Chaldeans”, referring to the various Babylonian garrisons now stationed throughout the land.

And it shall be well with you- "Amend" in the earlier appeals for repentance (e.g. Jer. 7:5) is the word here translated 'to do well to'. If they amended their ways, God would amend or change His plans of judgment. Here we behold the openness of God, His deep sensitivity to human repentance and change.

Jeremiah 40:10 As for me, behold, I will dwell at Mizpah, to stand before the Chaldeans who shall come to us-
Gedaliah like any true leader was leading the way by example; living in the land and serving the Chaldeans, as he had advised others to do.

But you, gather grapes and summer fruits and oil, and put them in your vessels, and dwell in your cities that you have taken- There had been a sudden reversal of everything. The abused majority had now been given the wealth and cities of the wealthy minority who had abused them. Dwelling in the cities taken suggests again the inheritance of the land after the exodus. There was really the possibility of a new start. The harvest had not been harvested by the wealthy, and so the poor took it for themselves.   

Jeremiah 40:11 Likewise when all the Jews who were in Moab, and among the children of Ammon, and in Edom, and who were in all the countries, heard that the king of Babylon had left a remnant of Judah, and that he had set over them Gedaliah the son of Ahikam, the son of Shaphan-
This dwelling of Israel's outcasts with Moab, Edom and Ammon was a repeat of what had happened during the previous Assyrian invasion (Is. 16:4). There were the same possibilities- of a miraculous Divine intervention and salvation.

Jeremiah 40:12 then all the Jews returned out of all places where they were driven, and came to the land of Judah to Gedaliah, to Mizpah, and gathered grapes and summer fruits very much-
As explained on :10, this was the harvest not gathered by the wealthy minority, due to the war. Again we see similarities with the entrance of Israel into the land, where they possessed cities and ate harvest which they had not planted. It seems there was the possibility of some restoration of the Kingdom of God in Israel through these who returned from where they had fled. Jer. 8:20 uses the same term to describe how the summer fruits had ended as a result of Divine judgment; but apparently the summer fruits had returned.

Jeremiah 40:13 Moreover Johanan the son of Kareah, and all the captains of the forces who were in the fields, came to Gedaliah to Mizpah-
Ishmael had presumably tried to get them to join in his plan of killing Gedaliah (:14); but Johanan and the other army commanders had refused to participate in the plot. Presumably they were of a mind to be obedient to Gedaliah's example of submitting to  Nebuchadnezzar as Yahweh's servant, as a form of submission to Yahweh. This would have been especially difficult for military men who had been resisting the Babylonians. And yet it seems that they were willing to do this; otherwise they would have sided with Ishmael's desperate bid for independence from Babylon.

Jeremiah 40:14 and said to him, Do you know that Baalis the king of the children of Ammon has sent Ishmael the son of Nethaniah to take your life? But Gedaliah the son of Ahikam didn’t believe them-
The king of Ammon may have been personally against Jeremiah after hearing his prophecies about Ammon of Jer. 27:3, and the demand that Ammon submit to Babylon and thence to Yahweh God of Israel. He therefore was against Gedaliah, who clearly was acting in obedience to Jeremiah's prophecies by submitting to Babylon (understanding Nebuchadnezzar as Yahweh's servant) as a form of submission to Yahweh.

Jeremiah 40:15 Then Johanan the son of Kareah spoke to Gedaliah in Mizpah secretly saying, Please let me go, and I will kill Ishmael the son of Nethaniah, and no man shall know it: why should he take your life, that all the Jews who are gathered to you should be scattered, and the remnant of Judah perish?-
Johanan thought that Ishmael's plan would lead to Babylonian vengeance to the point of them slaying all who remained in Judah. This is indeed the language of some of Jeremiah's prophecies; and yet this never happened, because in wrath God remembered mercy; or perhaps the mediation and repentance of a minority led to Him ameliorating His judgments. Ishmael did kill Gedaliah, and some of the Babylonians with him. And yet this total destruction of all Judah never happened; another testament to God's desperate grace and saving love toward His people.

Jeremiah 40:16 But Gedaliah the son of Ahikam said to Johanan the son of Kareah, You shall not do this thing; for you speak falsely of Ishmael
- Ishmael was from the royal family (Jer. 41:1), and therefore assumed that he ought to be the rightful ruler of Judah rather than Gedaliah, who was but a willing puppet of Babylon. But it was not then the time to restore the Kingdom and throne of David, and certainly not in the form of someone as deceitful as Ishmael. Ishmael clearly disbelieved the prophecies concerning the ending of the royal family. Perhaps Gedaliah's willing naivety about Ishmael was because he could not entertain any plan to slay a member of the royal family, remembering David's attitude to Saul.