Jeremiah 39:4

4 And it cometh to pass, when Zedekiah king of Judah, and all the men of war, have seen them, that they flee and go forth by night from the city, the way of the king's garden, through the gate between the two walls, and he goeth forth the way of the plain.

Jeremiah 39:4 Meaning and Commentary

Jeremiah 39:4

And it came to pass, [that] when Zedekiah the king of Judah
saw them, and all the men of war
That is, when Zedekiah and his soldiers saw the princes and generals of the Chaldean army enter the city through a breach made in the wall, and take possession of the middle gate; which they might see from some high tower where they were for safety, and to make their observation of the enemy: then they fled;
finding they were not able to keep their posts and resist the enemy: and went forth out of the city by night;
it being the middle of the night, as before observed out of Josephus, that the city was taken; and they took the advantage of the darkness of the night to make their escape: this they chose rather to do than to surrender to the Chaldeans, and lie at their mercy: and they went by the way of the king's garden, by the gate betwixt the two walls;
which lay either between the wall of the city and the outworks, as some; or between the old wall and the new one Hezekiah built, ( 2 Chronicles 32:5 ) ; as others; or rather between the wall of the city and the wall of the king's garden; this being a private way, they took it. The Jews have a fable, and which is related both by Jarchi and Kimchi, that there was a cave or vault underground, from the king's house to the plains of Jericho; and by this way the king went that he might not be seen; but God prepared a hind, which the Chaldean army saw, and pursued, and which went into the cave, add they after it; and when they were at the mouth of the cave they saw Zedekiah coming out of it, and took him: and he went out the way of the plain;
on the south side of the which led to Jericho; and on which side the kings garden was; not that he went alone, but his wives, and children, and princes, and men of war with him; see ( Jeremiah 52:7 ) .

Jeremiah 39:4 In-Context

2 in the eleventh year of Zedekiah, in the fourth month, in the ninth of the month, hath the city been broken up;
3 and come in do all the heads of the king of Babylon, and they sit at the middle gate, Nergal-Sharezer, Samgar-Nebo, Sarsechim, chief of the eunuchs, Nergal-Sharezer, chief of the Mages, and all the rest of the heads of the king of Babylon.
4 And it cometh to pass, when Zedekiah king of Judah, and all the men of war, have seen them, that they flee and go forth by night from the city, the way of the king's garden, through the gate between the two walls, and he goeth forth the way of the plain.
5 And the forces of the Chaldeans pursue after them, and overtake Zedekiah in the plains of Jericho, and they take him, and bring him up unto Nebuchadnezzar king of Babylon, to Riblah, in the land of Hamath, and he speaketh with him -- judgments.
6 And the king of Babylon slaughtereth the sons of Zedekiah, in Riblah, before his eyes, yea, all the freemen of Judah hath the king of Babylon slaughtered.
Young's Literal Translation is in the public domain.