What does Judges 9:40 mean?
ESV: And Abimelech chased him, and he fled before him. And many fell wounded, up to the entrance of the gate.
NIV: Abimelek chased him all the way to the entrance of the gate, and many were killed as they fled.
NASB: But Abimelech chased him, and he fled from him; and many fell wounded up to the entrance of the gate.
CSB: but Abimelech pursued him, and Gaal fled before him. Numerous bodies were strewn as far as the entrance of the city gate.
NLT: But Abimelech chased him, and many of Shechem’s men were wounded and fell along the road as they retreated to the city gate.
KJV: And Abimelech chased him, and he fled before him, and many were overthrown and wounded, even unto the entering of the gate.
NKJV: And Abimelech chased him, and he fled from him; and many fell wounded, to the very entrance of the gate.
Verse Commentary:
This is the anticlimactic explanation of the battle set up over the last several verses (Judges 9:30–39). When the fight happens, it is not much of a fight. Gaal's bold words to the leaders of Shechem against Abimelech (Judges 9:28–29) have led them to do battle with Abimelech and his forces. The leaders who initially put Abimelech in power (Judges 9:1–6) no longer want him to rule (Judges 9:22–25). They are in open rebellion against him, led by outspoken Gaal (Judges 9:26).

Despite Gaal's bravado and the rebellion of Shechem's leaders, Abimelech and his men are too powerful for them. Gaal sees which way things will go with the battle, so he runs for his life and escapes. Others are not so fortunate. Many of the leaders of the city fall near the city's eastern gate. The Hebrew root word describing those who fell is, most often translated as "kill, slay, pierced, or profaned." It's possible Abimelech made a point of maiming city leaders instead of killing them. It's also possible this comment includes both those wounded and killed outright, as when the term "casualties" is used in modern English.

Regardless of such details, Abimelech has defeated his former patrons. He will more thoroughly punish the rest of the city on the following day (Judges 9:42–45).
Verse Context:
Judges 9:22–57 describes the brutal fulfillment of Jotham's curse against his brother, Abimelech, and the leaders of the city of Shechem. God allows the two sides to be split by an evil spirit. First, Shechem's leaders attempt to kill Abimelech. Then they plot with a man named Gaal to overthrow him. Helped by his officer in the city, Abimelech and his men ambush Gaal and Shechem. They kill all the people and destroy the city. They then move on to the town of Thebez to do the same, but Abimelech is killed. Jotham's prediction of divine vengeance (Judges 9:19–20) comes true.
Chapter Summary:
Shechem's leaders conspire with a concubine's son to kill Gideon's other seventy sons. They make this man, Abimelech, their ruler. Gideon's youngest son survives, however, and delivers a curse. Using a fable, he says Abimelech and Shechem's leaders will destroy each other. God causes a division between Shechem's leaders and Abimelech. The noblemen attempt to kill Abimelech and unite behind a new leader. Abimelech discovers the plot and kills everyone in Shechem, destroying the city. When attacking a tower in a nearby town, however, Abimelech's skull is crushed by a thrown millstone. The curse is fulfilled.
Chapter Context:
Gideon successfully defeated Midianite raiders but declined to become Israel's official king. His sons, however, were held in high esteem during his remaining years (Judges 8). After Gideon's death, ambitious men conspire to kill almost all those heirs. This results in a series of bloody events. Eventually, judgment comes on those responsible. Israel fails to learn from the tragedies. Chapter 10 explains further idolatry and sin, before introducing the next major judge, Jephthah, in chapter 11.
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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