In Judges 1:16-21, the Kenites come to Israel: 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” (v 16).

The Kenites were a nomadic tribe linked to Moses through his father-in-law, Jethro (also called Reuel). When Moses fled Egypt after murdering an Egyptian, he lived among the Kenites and married and worked as a shepherd. The city of palms refers to Jericho, the first city which Israelite conquered through God’s power (Joshua 6).

In verse 17, we see the tribe of Judah fulfill their promise with Simeon which was made in verse 3:

“Come up with me into the territory allotted me, that we may fight against the Canaanites; and I in turn will go with you into the territory allotted you.”
(Judges 1:3)

 “Then Judah went with Simeon his brother, and they struck the Canaanites living in Zephath, and utterly destroyed it. So the name of the city was called Hormah” (v 17).

The tribes of Judah and Simeon successfully collaborate in their military efforts. The destruction of Zephath and its renaming to Hormah, meaning "destruction" or "devotion to destruction," signifies the completeness of their victory and their dedication of the city to the Lord by its total destruction (Numbers 21:3).

More military victories follow: Judah took Gaza with its territory and Ashkelon with its territory and Ekron with its territory (v 18). Judah extended its campaign to the Philistine cities of Gaza, Ashkelon, and Ekron , which were significant coastal cities. These cities, strategically located, were known for their fortified structures and strongholds. Judah's conquest of these territories demonstrates their expanding influence and control over the Promised Land. Their victories were not obtained with ease.

After consistent victory, Judah finally faces difficulty: “Now the Lord was with Judah, and they took possession of the hill country; but they could not drive out the inhabitants of the valley because they had iron chariots” (v 19).

Despite the Lord's presence and blessing, Judah is unable to fully drive out the inhabitants of the valley, primarily due to the technological advantage of iron chariots possessed by their enemies. This detail reflects the limitations and ongoing struggles of the Israelites against more technologically advanced foes.

While God was indeed with them, this failure prefigures future failures on their part as they enter a new season of hardship. Such a season should draw them toward the Lord in full submission and obedience, but unfortunately will cause them to lose hope and faith in Him.

Then they gave Hebron to Caleb, as Moses had promised; and he drove out from there the three sons of Anak (v 20). We first see that Hebron is given to Caleb, fulfilling the promise made to him by the Lord (Numbers 14:24; Joshua 14:6-15). Ever since God declared this blessing over him after he, Joshua, and the other spies returned from spying out the land, he had remembered it. Caleb goes to Joshua in Joshua 14 to ensure that he received this promised piece of land. It is not out of greed and selfishness that he does this. But he was given a gift from God for his faithfulness to God’s precepts, and he took diligent action to receive the gift.

Caleb, demonstrating his continued faith and strength, drives out the three sons of Anak, who were part of the formidable Anakim, known for their great size and strength (Deuteronomy 1:28). These three sons, Sheshai, Ahiman, and Talmai, are mentioned in Judges 1:10. The tribe of Judah fought them before handing over the land for Caleb to claim.

Another failure is then seen in the efforts of the Benjaminites: But the sons of Benjamin did not drive out the Jebusites who lived in Jerusalem; so the Jebusites have lived with the sons of Benjamin in Jerusalem to this day (v 21). In contrast to Judah's successes, the tribe of Benjamin fails to expel the Jebusites from Jerusalem.

This failure results in the coexistence of the Israelites and Jebusites in the city. It means an incomplete conquest of the land and the ongoing presence of native populations within Israelite territories.

This passage narrates the varied outcomes of Israel's efforts to possess the Promised Land, showcasing both successes and challenges. The integration of the Kenites, the strategic conquests by Judah, and the failures of Benjamin provide a nuanced picture of the complexities involved in establishing control over Canaan.

These verses display a realistic view of life’s trials. Even when doing his work, God’s people often face troubles. Yet, God is always faithful, and His people are called to be faithful to Him just as He is with us.

In this verse, we encounter the descendants of the Kenite, known for their connection to Moses' father-in-law, Jethro. The Kenites were a nomadic people who joined the Israelites on their journey into Canaan, likely settling around Jericho, referred to as the "city of palms." Their presence highlights the theme of alliances and cultural interactions in the region, reflecting how people groups intertwined during Israel's initial occupation of Canaan.

This commentary emphasizes the gradual shift in Israel's fidelity to God, a recurring theme throughout Judges. The Kenites’ participation foreshadows the complexities of coexistence, as they were not direct combatants yet lived in close proximity to the Israelites. This situation set the stage for the eventual compromises that plagued Israel, leading to an intermingling with the Canaanite cultures and the worship of their gods. The tendency to form uneasy alliances is echoed throughout the book, ultimately contributing to Israel's struggles with obedience and faithfulness to Yahweh as detailed in Judges 1:16.