‘And they took two princes of Midian, Oreb and Zeeb, and they slew Oreb at the rock of Oreb, and Zeeb they slew at the winepress of Zeeb, and pursued Midian. And they brought the heads of Oreb and Zeeb to Gideon, beyond Jordan.'
Chronologically this happened after Gideon had crossed the Jordan (compare Judges 8:4). This method of continuing a story until the end, followed by going back to a parallel story occurs regularly in ancient writings.
Oreb means Raven and Zeeb means Wolf. The Midianites appear to have favoured animal names. Compare how Moses' Midianite wife was called ‘little bird' (Zipporah - Exodus 2:21). Oreb and Zeeb were princes of Midian. But the ‘kings' appeared to have escaped. They had the fleetest camels. The rock and winepress were named after these events. The whole situation became a byword in Israel (Isaiah 9:4; Isaiah 10:26; Psalms 83:11). Out of all the sufferings of the people in Judges this one was most deeply remembered as the most terrible, for their enemy had tried to destroy them through starvation.