Judges 9:44

ESV Abimelech and the company that was with him rushed forward and stood at the entrance of the gate of the city, while the two companies rushed upon all who were in the field and killed them.
NIV Abimelek and the companies with him rushed forward to a position at the entrance of the city gate. Then two companies attacked those in the fields and struck them down.
NASB Then Abimelech and the company who was with him rushed forward and stood at the entrance of the city gate; the other two companies then attacked all who were in the field and killed them.
CSB Then Abimelech and the units that were with him rushed forward and took their stand at the entrance of the city gate. The other two units rushed against all who were in the countryside and struck them down.
NLT Abimelech and his group stormed the city gate to keep the men of Shechem from getting back in, while Abimelech’s other two groups cut them down in the fields.
KJV And Abimelech, and the company that was with him, rushed forward, and stood in the entering of the gate of the city: and the two other companies ran upon all the people that were in the fields, and slew them.
NKJV Then Abimelech and the company that was with him rushed forward and stood at the entrance of the gate of the city; and the other two companies rushed upon all who were in the fields and killed them.

What does Judges 9:44 mean?

This verse describes Abimelech's strategy to kill the people of Shechem who came out of the city into the fields. These are the regular citizens of Shechem. Perhaps they have come out to tend crops or to do other work. There's no indication any of these people were involved in the rebellion against Abimelech (Judges 9:22–25; 38–41). He seems intent on destroying everyone and everything in the city out of anger, or retribution, or perhaps pure spite.

Abimelech has set up three companies of his men, hidden in the fields, to ambush the people who come out of the city gates (Judges 9:42–43). They wait until all the people have reached the fields, then Abimelech's company rushes to the gate. Positioned there, they can block any escape back into the city. While they guard the entrance, the other two companies carry out the grim task of killing every citizen in the fields. These civilian field workers would have been completely defenseless against Abimelech's men.

This is not enough for Abimelech, however. He will now turn his wrath on the rest of the city (Judges 9:45).
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Context Summary
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.
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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.
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