What does Judges 9:25 mean?
ESV: And the leaders of Shechem put men in ambush against him on the mountaintops, and they robbed all who passed by them along that way. And it was told to Abimelech.
NIV: In opposition to him these citizens of Shechem set men on the hilltops to ambush and rob everyone who passed by, and this was reported to Abimelek.
NASB: The leaders of Shechem set up men in ambush against him on the tops of the mountains, and they robbed everyone who would pass by them on the road; and it was reported to Abimelech.
CSB: The citizens of Shechem rebelled against him by putting men in ambush on the tops of the mountains, and they robbed everyone who passed by them on the road. So this was reported to Abimelech.
NLT: The citizens of Shechem set an ambush for Abimelech on the hilltops and robbed everyone who passed that way. But someone warned Abimelech about their plot.
KJV: And the men of Shechem set liers in wait for him in the top of the mountains, and they robbed all that came along that way by them: and it was told Abimelech.
NKJV: And the men of Shechem set men in ambush against him on the tops of the mountains, and they robbed all who passed by them along that way; and it was told Abimelech.
Verse Commentary:
When it was convenient, the leaders of Shechem paid to help Abimelech kill his brothers (Judges 9:1–6). That let them gain control—or so it seemed—over the only son of Gideon not dead or in hiding. After only a few years, a divisive and hateful relationship has emerged. The same men who installed Abimelech as ruler now want to do him harm.

To accomplish this, they devise a scheme. The ambush described here might have begun as an assassination plot. This may have been thwarted if Abimelech spent most of his time in Arumah (Judges 9:41), instead. Either as a second plan, or part of the main plot, these ambushes are used to rob people traveling near the city.

Shechem was ideally located on a trade route, bringing business through the gates in the form of merchants and goods. Abimelech would likely have benefitted from this trade through taxes and tariffs. If word got out that merchants coming in and out of Shechem were being robbed by bandits, those wishing to do business would find other places to conduct it. Anyone with goods or money would have quickly learned to avoid Shechem, directly depriving King Abimelech of his income.

More treachery will follow, leading to terrible bloodshed (Judges 9:45).
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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