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Judges 7:25
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.

What does Judges 7:25 mean?

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.
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