What does Judges 20:39 mean?
ESV: the men of Israel should turn in battle. Now Benjamin had begun to strike and kill about thirty men of Israel. They said, “Surely they are defeated before us, as in the first battle.”
NIV: and then the Israelites would counterattack. The Benjamites had begun to inflict casualties on the Israelites (about thirty), and they said, 'We are defeating them as in the first battle.'
NASB: Then the men of Israel turned in the battle, and Benjamin began to strike and kill about thirty men of Israel, for they said, 'Undoubtedly they are defeated before us, as in the first battle.'
CSB: the men of Israel would return to the battle. When Benjamin had begun to strike them down, killing about thirty men of Israel, they said, "They're defeated before us, just as they were in the first battle."
NLT: When the Israelites saw the smoke, they turned and attacked Benjamin’s warriors. By that time Benjamin’s warriors had killed about thirty Israelites, and they shouted, 'We’re defeating them as we did in the first battle!'
KJV: And when the men of Israel retired in the battle, Benjamin began to smite and kill of the men of Israel about thirty persons: for they said, Surely they are smitten down before us, as in the first battle.
NKJV: whereupon the men of Israel would turn in battle. Now Benjamin had begun to strike and kill about thirty of the men of Israel. For they said, “Surely they are defeated before us, as in the first battle.”
Verse Commentary:
Israel's renewed battle plan has worked out extremely well (Judges 20:29–31). Instead of continuing to assail the city of Gibeah by direct attack (Judges 20:20–28), the Israelites have drawn Benjamin's army out from the city with a false retreat. When they were far enough away, a separate contingent of Israel's army attacked and defeated the city, killing all inside (Judges 20:29–38).

As Gibeah falls, the soldiers of Benjamin are confident they are routing the Israelites: chasing them down to finish them off. This verse repeats the previous statement that Benjamin has only killed about thirty Israelite fighters in this chase, adding to the illusion they have them on the run. The Benjaminites assume this battle is going the same way as the previous two and will end once again in Israel's defeat.

The retreating Israelites, however, are just waiting until they see the smoke of Gibeah's defeat appear in the sky. That's the designated signal to halt the false retreat, turn, and strike down Benjamin's army. When that smoke appears, even the Benjaminite army will realize what has happened (Judges 20:40–41).
Verse Context:
Judges 20:35–48 starts with a summary of the final conflict between the tribe of Benjamin and the rest of Israel. This is followed by details about how that result was obtained. The prior passage explained the other eleven tribes preparing for war, struggling, then eventually finding a winning strategy. Benjamin's armies are almost completely wiped out. Israel rages through the territory, destroying everything and everyone they encounter. Only 600 men remain alive out of the entire tribe.
Chapter Summary:
A massive army collected from eleven of the twelve tribes of Israel gather near the town of Gibeah. Their goal is to purge evil from the land (Judges 19:22–28). The tribe of Benjamin refuses to cooperate. Instead, they assemble an army about one-fifteenth the size of Israel's army. After two failed attempts and a promise of victory from the Lord, Israel uses a false retreat and ambush strategy to destroy Gibeah. This results in the loss of Benjamin's entire army. Israel's wrath spills over onto the territory, itself. All the people, animals, and towns in the tribe's territory are attacked, and it appears that only 600 Benjaminite men survive.
Chapter Context:
In the prior chapter, Benjaminite men of the town of Gibeah committed an act of heinous sin (Judges 19:22–25). In response, the murdered woman's husband rallies Israel with a gruesome message (Judges 19:29–30). Chapter 20 depicts how the tribe of Benjamin refuses to hand over the guilty men. Civil war ensues, resulting in near-total annihilation of their tribe. This creates a new crisis in Israel, as described in chapter 21; Israel doesn't want Benjamin to become extinct.
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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