It is interested that the Israelites were oppressed for 20 years before God responded by commanding the judge Deborah to raise up an army. She asked Barak to lead an army of 10,000 against Sisera the enemy army commander but he would not go without her. The Canaanites relied on their chariots for superiority and once they lost that advantage and were on foot the Israelites were able to rout them. Sisera was personally killed by a woman: Jael the wife of Heber. The story is important for that fact – women were involved with leading Israel and with providing for the defeat of her greatest enemy. Chapter five records the song of Deborah. This is the first chapter devoted to a song since that of Moses near the end of his life. She sings of the victory of the Lord and the defeat of Israel’s enemies.
Chapter six records how they were oppressed by the Midianites and other eastern peoples. God sent a prophet to announce that this was a result of their sin and then the angel of the Lord came to Gideon and told him that he had been selected to save Israel from her enemies. Gideon was quite hesitant and recounted his weak position among the people (like Moses). He also could not believe that it was really God speaking to him so he prepared an offering which God consumed with fire (like Elijah). Gideon was then commanded to destroy his father’s Baal altar and Asherah pole and build a proper altar. He did so and infuriated the townspeople but they were content to let Baal deal with him. He then put God to the test with the famous “Gideon’s fleece” account in which he twice tested God to ensure that he wasn’t committing suicide by going into battle against their powerful enemies. Rather than demonstrating Gideon’s weakness of faith I think it demonstrates the strength of their enemies and the miraculous nature of the subsequent victory.