What does Judges 1:20 mean?
ESV: And Hebron was given to Caleb, as Moses had said. And he drove out from it the three sons of Anak.
NIV: As Moses had promised, Hebron was given to Caleb, who drove from it the three sons of Anak.
NASB: Then they gave Hebron to Caleb, as Moses had promised; and he drove out from there the three sons of Anak.
CSB: Judah gave Hebron to Caleb, just as Moses had promised. Then Caleb drove out the three sons of Anak who lived there.
NLT: The town of Hebron was given to Caleb as Moses had promised. And Caleb drove out the people living there, who were descendants of the three sons of Anak.
KJV: And they gave Hebron unto Caleb, as Moses said: and he expelled thence the three sons of Anak.
NKJV: And they gave Hebron to Caleb, as Moses had said. Then he expelled from there the three sons of Anak.
Verse Commentary:
The writer of Judges sums up the effectiveness of Judah's campaign to conquer their allotted territory in the Promised Land (Judges 1:4–11, 16–19). They succeeded in taking the hill country, but they failed to overcome the armies of the plains with their iron chariots. This was likely due to Judah's own disobedience or lack of faith.

Now the writer mentions, again, that Caleb, of the tribe of Judah, succeeded in securing Hebron and its surrounding area. This is the territory he had requested for himself, and it had been given to him by Joshua (Joshua 14:11–14). Caleb drove out the descendants of Anak in Hebron. The Anakites were the impressively large and imposing warriors Caleb insisted that Israel could defeat with God's help several decades earlier (Numbers 13:30). He had done exactly that, with the Lord's blessing, when he was given the opportunity.
Verse Context:
Judges 1:1–20 describes the campaign of the tribes of Judah and Simeon, to drive out or destroy all the Canaanites from their large territory in southern Israel. It begins with victories over Bezek and Jerusalem. The report rehearses the former victories by Caleb and his family in the hill country. The campaign continues into the desert wilderness of the Negeb, where a group of descendants of Moses' father-in-law settles. Judah dominates the hill country but doesn't entirely evict the wicked Canaanites because of their iron chariots.
Chapter Summary:
Judges 1 summarizes the early efforts of the tribes of Israel to drive the Canaanites from the land or to destroy them entirely (Deuteronomy 7:1–5; 9:4). The process starts well with a string of successes by Judah and Simeon in the south. Then the news turns sour as one tribe after another is said to have failed to drive the Canaanites out of their allotted territories. Instead, they occupy certain territories, often allowing inhabitants of the land to live among them.
Chapter Context:
Judges 1 continues immediately from the death of Joshua (Joshua 24:29–30). It begins a new era for Israel, now referred to as the time of "the judges." In a series of reports, tribe by tribe, the narrator describes Israel's success or failure to drive the deeply wicked Canaanites (Deuteronomy 7:1–5; 9:4) from the land or to destroy them. Judah experiences much success, but it is unable to drive the inhabitants out of one region, at least. Every other tribe either fails utterly to remove the Canaanites, or only gradually grows strong enough to capture the territory.
Book Summary:
The Book of Judges describes Israel's history from the death of Joshua to shortly before Israel's first king, Saul. Israel fails to complete God's command to purge the wicked Canaanites from the land (Deuteronomy 7:1–5; 9:4). This results in a centuries-long cycle where Israel falls into sin and is oppressed by local enemies. After each oppression, God sends a civil-military leader, labeled using a Hebrew word loosely translated into English as "judge." These appointed rescuers would free Israel from enemy control and govern for a certain time. After each judge's death, the cycle of sin and oppression begins again. This continues until the people of Israel choose a king, during the ministry of the prophet-and-judge Samuel (1 Samuel 1—7).
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