What does Judges 20:44 mean?
ESV: Eighteen thousand men of Benjamin fell, all of them men of valor.
NIV: Eighteen thousand Benjamites fell, all of them valiant fighters.
NASB: So eighteen thousand men of Benjamin fell; all of these were valiant men.
CSB: There were eighteen thousand men who died from Benjamin; all were warriors.
NLT: That day 18,000 of Benjamin’s strongest warriors died in battle.
KJV: And there fell of Benjamin eighteen thousand men; all these were men of valour.
NKJV: And eighteen thousand men of Benjamin fell; all these were men of valor.
Verse Commentary:
This summarizes the death toll for Benjaminite fighters during the first stage of their flight from a surrounding Israeli army. The men are described as "men of valor." In this context, this is a gesture of respect. The men were brave fighters to the last, not cowards or weak men. The text does not celebrate their deaths at the hands of Israel. This is a sobering moment for all involved.

The hunt for the fleeing men of Benjamin is not complete, however. Israel's soldiers had nearly surrounded Benjamin's army over a large area as they fled toward the wilderness. Some are still attempting to break out of the net.

The Hebrew term 'eleph can refer to "groups" or "divisions" or to "thousands," and either interpretation is possible here. Ultimately, the main point is that only a tiny fraction of Benjamin's original forces (Judges 20:15) will survive this conflict (Judges 20:46).
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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