What does Judges 7:25 mean?
ESV: And they captured the two princes of Midian, Oreb and Zeeb. They killed Oreb at the rock of Oreb, and Zeeb they killed at the winepress of Zeeb. Then they pursued Midian, and they brought the heads of Oreb and Zeeb to Gideon across the Jordan.
NIV: They also captured two of the Midianite leaders, Oreb and Zeeb. They killed Oreb at the rock of Oreb, and Zeeb at the winepress of Zeeb. They pursued the Midianites and brought the heads of Oreb and Zeeb to Gideon, who was by the Jordan.
NASB: And they captured the two leaders of Midian, Oreb and Zeeb, and they killed Oreb at the rock of Oreb, and they killed Zeeb at the wine press of Zeeb, while they pursued Midian; and they brought the heads of Oreb and Zeeb to Gideon from across the Jordan.
CSB: They captured Oreb and Zeeb, the two princes of Midian; they killed Oreb at the rock of Oreb and Zeeb at the winepress of Zeeb, while they were pursuing the Midianites. They brought the heads of Oreb and Zeeb to Gideon across the Jordan.
NLT: They captured Oreb and Zeeb, the two Midianite commanders, killing Oreb at the rock of Oreb, and Zeeb at the winepress of Zeeb. And they continued to chase the Midianites. Afterward the Israelites brought the heads of Oreb and Zeeb to Gideon, who was by the Jordan River.
KJV: And they took two princes of the Midianites, Oreb and Zeeb; and they slew Oreb upon the rock Oreb, and Zeeb they slew at the winepress of Zeeb, and pursued Midian, and brought the heads of Oreb and Zeeb to Gideon on the other side Jordan.
NKJV: And they captured two princes of the Midianites, Oreb and Zeeb. They killed Oreb at the rock of Oreb, and Zeeb they killed at the winepress of Zeeb. They pursued Midian and brought the heads of Oreb and Zeeb to Gideon on the other side of the Jordan.
Verse Commentary:
Gideon's combat strategy is once again successful. He and his forces pursue the army of Midian (Judges 7:19–24) as they flee east to cross the Jordan River and escape. Gideon sent fast messengers to the men of Ephraim, closer to the Jordan River, to secure the crossing places the Midianites might use, cutting off their retreat.

This tactic seems to have worked, but not perfectly. Apparently, some of the Midianite army was able to make it across the Jordan, but they do not get far before Ephraimite fighters chase them down. They capture and kill two princes of Midian: Oreb and Zeeb. They name the places where these members of the Midianite royal family are killed accordingly. Thus, Oreb is killed by the Israelites at what is then called "the rock of Oreb," and Zeeb is killed at what becomes known as "the winepress of Zeeb." This part of Israel's victory is commemorated in one of the psalms (Psalm 83:11) and mentioned in the book of Isaiah (Isaiah 10:26).

The Ephraimite soldiers bring the heads of these men back across the Jordan River, presenting them to Gideon as trophies of battle.
Verse Context:
Judges 7:19–25 describes the Lord's victory over the Midianites through Gideon and his 300 men. The Israelites take positions around the Midianite camp well after dark. They choose a strategic moment to attack: just after the changing of the guard. Nearly in unison, the Israelite soldiers blow trumpets and shout battle cries while exposing torches. The Midianites panic, assuming the enemy force is massive. In the dark, and in a panic, they begin attacking each other. The chaos leads them to flee toward the Jordan River. Gideon calls for men from several tribes to join him in chasing them down. He sends messengers to Ephraim to tell them to cut off the fleeing enemy at the Jordan River. The Midianites do not escape.
Chapter Summary:
Gideon and his 32,000–man army of volunteer Israelites camp in the hills above the Midianite invaders in the valley. The Lord tells Gideon to reduce his troops until only 300 remain. God allows Gideon to overhear the interpretation of a Midianite dream, an event that strengthens his faith. Gideon and his 300 men take positions around the Midianite camp and blow trumpets, hold up torches, and shout battle cries. Those in the camp panic and begin attacking each other. The survivors flee toward the Jordan but are eventually cut off.
Chapter Context:
Despite a miraculous calling from God, and success in his first actions, Gideon still expressed doubt (Judges 6). After seeing two custom-requested miracles, Gideon prepares to attack the Midianite invaders. He winnows his army down to only 300 men and overhears an encouraging conversation. Gideon and his men surprise the enemy after nightfall with trumpets and torches, sparking a panic. This begins a rout of the enemy. In the next chapter, Gideon succeeds further despite stubbornness from his own people (Judges 8).
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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