What does Judges 11:3 mean?

Some of Israel's greatest heroes came from unlikely beginnings. Gideon, the previous judge, was hiding his food from the enemy when an angel commissioned him to fight (Judges 6:11–12). Jephthah will become a renowned rescuer of Israel, despite his own humble origins. Not only is he the son of a prostitute, but also his own brothers ran him out of the family to avoid sharing inheritance with him. Jephthah is on his own, socially and economically.

Jephthah flees to a region described as the land of Tob. Some scholars believe this to be an area in Gilead somewhere west of Mount Hauron, though the evidence is not conclusive. There, he proves to be a charismatic figure and natural leader. Alone in a strange territory, he begins to attract a following. His fellows are not the best and brightest of their culture; these are men on the less reputable side of society and the law. In fact, they are described using the same term given to Abimelech's hired goons (Judges 9:4). These are men of low moral character.

That Jephthah "goes out" with such men implies a party of bandits. This group might have raided towns or other targets to make their living. Jephthah's reputation may have developed in much the same way as did famous pirates, known and feared for their exploits.