1. Israel Fights the Remaining Canaanites
In this passage, Israel embarks on its first military campaign since the death of Joshua. Judah and Simeon defeat the Canaanites and Perizzites, including their leader, Adoni-Bezek. The account from Joshua 15 of Caleb giving his daughter Acsah in marriage to Othniel - and providing her with springs of water - is retold here. Several tribes are also implicitly chastised for not driving out the Canaanites in their assigned territories; instead, those tribes enslaved the Canaanites.
We see that while God was with the Israelites in giving them the Promised Land, they failed to obey Him completely by possessing all of their assigned territories. This failure sets the stage for Israel's struggles with obedience throughout the remainder of Judges.
2. The Angel of the Lord at Bokim
In this passage, an angel of the Lord comes to the Israelites at Bokim and states that since they have failed to obey the Lord, He will cause the surviving Canaanites in their assigned territories to ensnare them. This declaration spurs the Israelites to weep and offer sacrifices to God.
One must wonder if the Israelites were merely trying to appease God by weeping and offering sacrifices to Him. Perhaps they figured that if they appeased Him at that time, He would not use their neighbors to ensnare them - and then they could continue sinning without any repercussions.
3. Disobedience and Defeat
In this passage, it is noted that after Joshua and the generation of Israelites who he led into the Promised Land passed away, the next generation of Israelites failed to obey the Lord. Instead, they worshiped Baal and the Ashtoreths; thus, the Lord punished them by 1) sending raiders to plunder them and 2) having their neighbors enslave them. The Israelites also intermarried with their neighbors; thankfully, the Lord would frequently rescue them by raising up judges.
In verse 22 of chapter 2, the Lord states that He will use the surviving Canaanites "to test Israel." This is a rather interesting statement, as it implies that in terms of God's covenant, "the ball was in Israel's court." The question, then, was whether Israel would be able to pass this test. We see that Israel is ultimately responsible for its actions.
4. Othniel
In this passage, Israel serves the Baals and the Asherahs; they are then enslaved by Cushan-Rishathaim, the king of Aram Naharaim. After eight years of slavery, they cry out to the Lord and He rescues them by raising up Othniel. They then enjoy forty years of peace until Othniel dies.
Clearly Cushan-Rishathaim was a rather harsh slave-owner.
5. Ehud
In this passage, Israel breaks its covenant with the Lord; they are then enslaved by Eglon, the king of Moab - who enlists the Ammonites and Amalekites to help him subdue Israel. After eighteen years of slavery, they cry out to the Lord and He rescues them by raising up Ehud. In this case, Ehud kills Eglon by taking advantage of the fact that he is a southpaw. Israel then enjoys eighty years of peace.
I have always found this passage to be strangely amusing, especially as Eglon was so fat that, as noted in verse 22 of chapter 3, "the fat closed in over" Ehud's sword. Eglon's servants are also due for criticism, as they failed to properly "pat down" Ehud when he initially visited Eglon.
6. Shamgar
In this passage, the Lord raises up another judge, Shamgar, who kills 600 Philistines with an oxgoad.
One must wonder if Shamgar killed all 600 Philistines in a single battle - or if he killed them over several engagements. He must have been rather skillful with an oxgoad.