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Judges 1:8

Adam Clarke
Bible Commentary

Had fought against Jerusalem - We read this verse in a parenthesis, because we suppose that it refers to the taking of this city by Joshua; for as he had conquered its armies and slew its king, Joshua 10:26, it is probable that he took the city: yet we find that the Jebusites still dwelt in it, Joshua 15:63; and that the men of Judah could not drive them out, which probably refers to the strong hold or fortress on Mount Zion, which the Jebusites held till the days of David, who took it, and totally destroyed the Jebusites. See 2 Samuel 5:6-9, and 1 Chronicles 11:4-8. It is possible that the Jebusites who had been discomfited by Joshua, had again become sufficiently strong to possess themselves of Jerusalem; and that they were now defeated, and the city itself set on fire: but that they still were able to keep possession of their strong fort on Mount Zion, which appears to have been the citadel of Jerusalem.

Albert Barnes
Notes on the Whole Bible

Render “and the children of Judah fought against Jerusalem, and took it, and smote it,” etc. With regard to the capture of Jerusalem there is some obscurity. It is here said to have been taken, smitten with the edge of the sword, and burned, by the children of Judah. In Joshua 12:8, Joshua 12:10 the Jebusite and the king of Jerusalem are enumerated among Joshua‘s conquests, but without any distinct mention of the capture of the city; and in the marginal reference we read that the Jebusites were not expelled from Jerusalem, but dwelt with the children of Judah (compare Judges 1:21). Further, we learn from Judges 19:10-12 that Jerusalem was wholly a Jebusite city in the lifetime of Phinehas Judges 20:28, and so it continued until the reign of David 2 Samuel 5:6-9. The conclusion is that Jerusalem was only taken once, namely, at the time here described, and that this was in the lifetime of Joshua; but that the children of Judah did not occupy it in sufficient force to prevent the return of the Jebusites, who gradually recovered complete possession.

Set the city on fire - A phrase found only at Judges 20:48; 2 Kings 8:12, and Psalm 74:7.

Matthew Henry
Concise Bible Commentary
The Israelites were convinced that the war against the Canaanites was to be continued; but they were in doubt as to the manner in which it was to be carried on after the death of Joshua. In these respects they inquired of the Lord. God appoints service according to the strength he has given. From those who are most able, most work is expected. Judah was first in dignity, and must be first in duty. Judah's service will not avail unless God give success; but God will not give the success, unless Judah applies to the service. Judah was the most considerable of all the tribes, and Simeon the least; yet Judah begs Simeon's friendship, and prays for aid from him. It becomes Israelites to help one another against Canaanites; and all Christians, even those of different tribes, should strengthen one another. Those who thus help one another in love, have reason to hope that God will graciously help both. Adoni-bezek was taken prisoner. This prince had been a severe tyrant. The Israelites, doubtless under the Divine direction, made him suffer what he had done to others; and his own conscience confessed that he was justly treated as he had treated others. Thus the righteous God sometimes, in his providence, makes the punishment answer the sin.
Cross References
Related Verses
The Limits of Israelite Settlement
The Period of the Judges