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Judges 2:18 - And when the LORD raised them up judges, then the LORD was with the judge, and delivered them out of the hand of their enemies all the days of the judge: for it repented the LORD because of their groanings by reason of them that oppressed them and vexed them.
Before he died, Joshua urged Israel to keep trusting God and obeying His commands, but they didn't. After Joshua died, "every man did what was right in his own eyes". They would forget God, the enemy would severely oppress them, they would cry out to God for help, and God would raise up a deliverer (Judge) to free them of their misery. This was the sad pattern for the Israelites for almost 400 years. The main deliverer-judges were: Othniel, Deborah, Gideon, Jephthah, Samson, Eli, and Samuel. (Ruth also lived during this period). Probably the most important person in this era was Samuel.
Judges 2:10-19 When all that generation had been gathered to their fathers, another generation arose after them who did not know the LORD nor the work which He had done for Israel. Then the children of Israel did evil in the sight of the LORD, and served the Baals; and they forsook the LORD God of their fathers, who had brought them out of the land of Egypt; and they followed other gods from among the gods of the people who were all around them, and they bowed down to them; and they provoked the LORD to anger.
They forsook the LORD and served Baal and the Ashtoreths. And the anger of the LORD was hot against Israel. So He delivered them into the hands of plunderers who despoiled them; and He sold them into the hands of their enemies all around, so that they could no longer stand before their enemies. Wherever they went out, the hand of the LORD was against them for calamity, as the LORD had said, and as the LORD had sworn to them. And they were greatly distressed. Nevertheless, the LORD raised up judges who delivered them out of the hand of those who plundered them. Yet they would not listen to their judges, but they played the harlot with other gods, and bowed down to them.
They turned quickly from the way in which their fathers walked, in obeying the commandments of the LORD; they did not do so. And when the LORD raised up judges for them, the LORD was with the judge and delivered them out of the hand of their enemies all the days of the judge; for the LORD was moved to pity by their groaning because of those who oppressed them and harassed them. And it came to pass, when the judge was dead, that they reverted and behaved more corruptly than their fathers, by following other gods, to serve them and bow down to them. They did not cease from their own doings nor from their stubborn way.
The message that seems to become evident during the dark period of the judges is that man is inherently sinful and will always revert back to his evil ways, and the Lord will always be there for those who cry out to Him, but forgetting God can only result in bondage and defeat.