The times were dark. There arose a generation that did not know the Lord nor the mighty things that He had done for Israel. In other words, an entire generation lived in the lap of luxoury without really understanding who it was that brought them there or the great things God had accomplished despite all odds through Moses and Joshua. The answer to this problem: the new generation had to learn war.
God clearly lined out for the children of Israel what would happen if they did not fully obey Him when they entered the land. They, through apathy and indifference to God's word, chose captivity in the land. Through apathy they decided to do what was right in their own eyes rather than what God had said--anarchy. As always, anarchy leads to absolute chaos-apostacy. God sold His chosen people into the hands of the enemy. Judges 3 vividly paints this picture--Israel would sin (Idolatry); God would hand them over to their enemy; Israel would cry out (A cry for relief and not a godly sorrow that led to repentance); God would raise up a deliverer; the deliever would die; the people would return to their wicked ways.
Enter stage left... the warrior, the strategizer, and the beast: Othniel, Ehud, and Shamgar. Their situation speaks volumes to us, as we consider how to lead a captive people toward the liberation of the gospel.