What does Judges 1:16 mean?
ESV: And the descendants of the Kenite, Moses ' father-in-law, went up with the people of Judah from the city of palms into the wilderness of Judah, which lies in the Negeb near Arad, and they went and settled with the people.
NIV: The descendants of Moses’ father-in-law, the Kenite, went up from the City of Palms with the people of Judah to live among the inhabitants of the Desert of Judah in the Negev near Arad.
NASB: Now the descendants of the Kenite, Moses’ father-in-law, went up from the city of palms with the sons of Judah, to the wilderness of Judah which is in the south of Arad; and they went and lived with the people.
CSB: The descendants of the Kenite, Moses’s father-in-law, had gone up with the men of Judah from the City of Palms to the Wilderness of Judah, which was in the Negev of Arad. They went to live among the people.
NLT: When the tribe of Judah left Jericho — the city of palms — the Kenites, who were descendants of Moses’ father-in-law, traveled with them into the wilderness of Judah. They settled among the people there, near the town of Arad in the Negev.
KJV: And the children of the Kenite, Moses' father in law, went up out of the city of palm trees with the children of Judah into the wilderness of Judah, which lieth in the south of Arad; and they went and dwelt among the people.
NKJV: Now the children of the Kenite, Moses’ father-in-law, went up from the City of Palms with the children of Judah into the Wilderness of Judah, which lies in the South near Arad; and they went and dwelt among the people.
Verse Commentary:
The people of Judah have been conquering their allotted territory in the Promised Land from north to south. They started near Jerusalem and are now approaching the Negeb, the large, desert wilderness at the south end of Israel's and Judah's borders (Judges 1:4–10).

Meanwhile, a group of people who are not Israelites travels to the Negeb to make their own homeland there. These are the descendants of Moses' father-in-law, who was a Midian priest. Scholars speculate that this group was descended from the same Midianites that Moses invited to come to the Promised Land with the Israelites (Numbers 10:29–32).

This group is said to come from the "city of palms." That is one of the names for Jericho, but Bible scholars suggest it is likely also the name for a city called Tamar south of the Dead Sea. If so, this group is claiming their place in the Negeb as Judah's army is securing that area.

The troubling note, though, is that this group settled with the people in the Negeb. Neither they nor Judah drove the local Canaanites out or destroyed them. This is another violation of God's directive to Israel to devote the inhabitants of the land to destruction so that they do not influence Israel to worship other gods (Deuteronomy 20:16–18).
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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