To understand the story of Samson and Delilah, it is important to go back to Genesis to set the stage for what is truly happening in the story. God made a covenant with Abraham:

ESV Genesis 17:7 And I will establish my covenant between me and you and your offspring after you throughout their generations for an everlasting covenant, to be God to you and to your offspring after you. 8 And I will give to you and to your offspring after you the land of your sojournings, all the land of Canaan, for an everlasting possession, and I will be their God.” 9 And God said to Abraham, “As for you, you shall keep my covenant, you and your offspring after you throughout their generations.

As we can see from this passage, God gave Israel, Abraham’s descendants, the land of Canaan and Israel was to keep God’s covenant by circumcising their sons.
God told Abraham that Israel would be sent into Egypt and would live in captivity until is was time for the judgment of the Amorites who inhabit the land of Canaan:

ESV Genesis 15:13 Then the LORD said to Abram, “Know for certain that your offspring will be sojourners in a land that is not theirs and will be servants there, and they will be afflicted for four hundred years. 14 But I will bring judgment on the nation that they serve, and afterward they shall come out with great possessions. 15 As for yourself, you shall go to your fathers in peace; you shall be buried in a good old age. 16 And they shall come back here in the fourth generation, for the iniquity of the Amorites is not yet complete.”

God kept His promise and brought the people out of the land of Egypt but before He lead them into the promised land He prepared them to be His people by giving them the law:

ESV Exodus 19:1 On the third new moon after the people of Israel had gone out of the land of Egypt, on that day they came into the wilderness of Sinai. 2 They set out from Rephidim and came into the wilderness of Sinai, and they encamped in the wilderness. There Israel encamped before the mountain, 3 while Moses went up to God. The LORD called to him out of the mountain, saying, “Thus you shall say to the house of Jacob, and tell the people of Israel: 4 You yourselves have seen what I did to the Egyptians, and how I bore you on eagles’ wings and brought you to myself. 5 Now therefore, if you will indeed obey my voice and keep my covenant, you shall be my treasured possession among all peoples, for all the earth is mine; 6 and you shall be to me a kingdom of priests and a holy nation. These are the words that you shall speak to the people of Israel.” 7 So Moses came and called the elders of the people and set before them all these words that the LORD had commanded him. 8 All the people answered together and said, “All that the LORD has spoken we will do.” And Moses reported the words of the people to the LORD.

Now part of their covenantal duty was to live by the commandments of God and this included:

ESV Deuteronomy 7:1 “When the LORD your God brings you into the land that you are entering to take possession of it, and clears away many nations before you, the Hittites, the Girgashites, the Amorites, the Canaanites, the Perizzites, the Hivites, and the Jebusites, seven nations more numerous and mightier than yourselves, 2 and when the LORD your God gives them over to you, and you defeat them, then you must devote them to complete destruction. You shall make no covenant with them and show no mercy to them. 3 You shall not intermarry with them, giving your daughters to their sons or taking their daughters for your sons, 4 for they would turn away your sons from following me, to serve other gods. Then the anger of the LORD would be kindled against you, and he would destroy you quickly. 5 But thus shall you deal with them: you shall break down their altars and dash in pieces their pillars and chop down their Asherim and burn their carved images with fire. 6 “For you are a people holy to the LORD your God. The LORD your God has chosen you to be a people for his treasured possession, out of all the peoples who are on the face of the earth.

God brought them into the promised land as he promised. He went before them and gave the enemy into their hand. Israel had to fight to take possession of the land but the Lord gave them the ability to do so. Even though the Lord delivered them and did as He promised to do, they did not keep God’s commandments:

ESV Judges 2:1 Now the angel of the LORD went up from Gilgal to Bochim. And he said, “I brought you up from Egypt and brought you into the land that I swore to give to your fathers. I said, ‘I will never break my covenant with you, 2 and you shall make no covenant with the inhabitants of this land; you shall break down their altars.’ But you have not obeyed my voice. What is this you have done? 3 So now I say, I will not drive them out before you, but they shall become thorns in your sides, and their gods shall be a snare to you.”

ESV Judges 3:1 Now these are the nations that the LORD left, to test Israel by them, that is, all in Israel who had not experienced all the wars in Canaan. 2 It was only in order that the generations of the people of Israel might know war, to teach war to those who had not known it before. 3 These are the nations: the five lords of the Philistines and all the Canaanites and the Sidonians and the Hivites who lived on Mount Lebanon, from Mount Baal-hermon as far as Lebo-hamath. 4 They were for the testing of Israel, to know whether Israel would obey the commandments of the LORD, which he commanded their fathers by the hand of Moses. 5 So the people of Israel lived among the Canaanites, the Hittites, the Amorites, the Perizzites, the Hivites, and the Jebusites. 6 And their daughters they took to themselves for wives, and their own daughters they gave to their sons, and they served their gods. 7 And the people of Israel did what was evil in the sight of the LORD. They forgot the LORD their God and served the Baals and the Asheroth. 8 Therefore the anger of the LORD was kindled against Israel, and he sold them into the hand of Cushan-rishathaim king of Mesopotamia. And the people of Israel served Cushan-rishathaim eight years.

The people cried out to the Lord and He raised up a deliverer (judge):

ESV Judges 3:9 But when the people of Israel cried out to the LORD, the LORD raised up a deliverer for the people of Israel, who saved them, Othniel the son of Kenaz, Caleb’s younger brother. 10 The Spirit of the LORD was upon him, and he judged Israel. He went out to war, and the LORD gave Cushan-rishathaim king of Mesopotamia into his hand. And his hand prevailed over Cushan-rishathaim. 11 So the land had rest forty years. Then Othniel the son of Kenaz died.

And again the people sinned against the Lord:

ESV Judges 3:12 And the people of Israel again did what was evil in the sight of the LORD, and the LORD strengthened Eglon the king of Moab against Israel, because they had done what was evil in the sight of the LORD. 13 He gathered to himself the Ammonites and the Amalekites, and went and defeated Israel. And they took possession of the city of palms. 14 And the people of Israel served Eglon the king of Moab eighteen years.

And again the people cried out and the Lord raised up a deliverer. This cycle is repeated throughout the book of Judges until Samson. Samson is the last of the judges. It is important to understand this before you study Samson and Delilah and it is one of the reason I entitled this discussion, “Samson Before Delilah: Beyond the Sunday School Lessons.”
Updated to add: Go here for more of the study.
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