Once Israel settled in their land and their beloved leader that led them into their permanent home died, Israel began to do what God wanted them to do: to begin conquering and running out the remaining Canaanite nations that they didn’t drive out when they conquered the majority of the land. So they decided to run them out by tribal land. So the men of Israel (most likely) went to the temple in Shiloh and asked God which tribe should go first to fight the remaining Canaanites in their land:
Judges 1:1
“After the death of Joshua, the Israelites asked the Lord, ‘Who of us is to go up first to fight against the Canaanites?’ ”
God (most likely through the Aaronite priest) answered Israel back by saying the tribe of Judah should go first because he would fight for them first: they would completely get rid of all the Canaanites:
Judges 1:2
“The Lord answered, ‘Judah shall go up; I have given the land into their hands.’”
So the tribe of Judah (and Simenon in partnering with Judah) took the lead in finishing the job of exterminating the remaining Canaanite nations:
Judges 1:3
“The men of Judah then said to the Simeonites their fellow Israelite, ‘Come up with us into the territory allotted to us, to fight against the Canaanites. We in turn will go with you into yours.’ So the Simeonites went with them.”
So, with the help of the army of Simeon Judah began to conquer the remaining Canaanite nations in their land, then other tribes (most likely as they were lead by God to do) began to fight against the remaining Canaanite nations in their land
Judges 1:4
“When Judah attacked, the Lord gave the Canaanites and Perizzites into their hands,…”
Once they conquered most of the Canaanite nations in their land they then helped the tribe of Simeon by going in to their land and helping them conquer the remaining Canaanite nations in their land:
Judges 1:17
“Then the men of Judah went with the Simeonites…[into their land]…and attacked the Canaanites living in [it]…”
Next (God most likely ordered) the tribes of Joseph (Ephraim and Manasseh)/possibly the rest of the tribes to begin fighting against the remaining Canaanites of their land, so the tribes of Joseph began to fight the remaining Canaanites:
Judges 1:22
“Now the tribes of Joseph attacked [the Canaanites], and the Lord was with them [so they conquered and destroyed them].”
During this time, the original generation who originally got to see God not only punish them and their parent in the wilderness for 40 years but also saw their God protect them and miraculously fight for them from all the much stronger and even giant nations of Canaan faithfully served God and kept his covenant to obey every word he commanded them to do as his people immediately got to work obeying the orders of their God through Joshua and Moses to get rid of the remaining Canaanite nations.
Judges 2:7
“The people served the Lord throughout the lifetime of Joshua and of the elders who outlived him…[those]… who had seen all the great things the Lord had done for Israel.”
However as this original generation began to fight and run out the remaining Canaanite nations many years/decades went by this generation began to die from old age and their children who had been born in the promise land never seeing the great miracles God had done for their parents and didn’t really know about their God in the way their parents got to know about them:
Judges 2:2:10
“After that whole generation had been gathered to their ancestors (died), another generation grew up who knew neither the Lord nor what he had done for Israel.”
Even though their parents had died their was still some Canaanite nations left to conquer, it was up to their children finish off the Canaanite nation remaining in Israel, but this generation saw how determined and support (and even how strong) some of these Canaanite nations had been so they decided to stop conquering them and taking their land and instead let them continue to live in their land alongside them after all there was enough land for all of them now:
Judges 1:27
“But…[Israel]…did not drive out the [remaining Canaanite nations]…and their surrounding settlements, for the Canaanites were determined to live in that land.”
So this generation of Israelite became more tolerant to the Canaanites and lived with them in peace it seems:
Judges 1:32
“The [Israelites] lived among the Canaanite inhabitants of the land because they did not drive them out.”
Eventually as some generations more passed Israel became more powerful in their land as they grew in number and eventually were able to enslaved the remaining Canaanite nations to do labor for them:
Judges 1:27-28
“…When Israel became strong, they pressed the Canaanites into forced labor but never drove them out completely.”
This was complete disobedience to God’s command to Israel to completely kill/drive all the Canaanites out of their land! Israel had once again disobeyed God’s commands and was breaking his covenant to obey all his commands. So God (as the angel of the Lord) manifested to Israel and went through the land telling them his disappointment in his people rejecting his orders to conquer and kill the remaining Canaanites:
Judges 2:1-3
“The angel of the Lord went up from Gilgal to Bokim and said, ‘I brought you up out of Egypt and led you into the land I swore to give to your ancestors. I said,
(quoting command he told to Moses recorded in Exodus 34:12-13 and Exodus 23:32-33)
‘…you shall not make a covenant with the people of this land, but you shall break down their altars.’
Yet you have disobeyed me. Why have you done this?’”
“…And I have also said,
(quoting the command he told to Moses recorded in Exodus 34:12-13 and Exodus 23:33)
‘[if you]…will not drive them out…; they will become traps for you, and their gods will become snares to you.’”
and told them since he rejected his commands he would no longer drive out these remaining Canaanites (let alone help them conquer more of their land from other natives) but like he promised through Joshua and Moses they would now be traps for his people that would corrupt them until they were destroyed from the land God gave them!
What terrible news they failed their God and doomed themselves!!!
The Israelites who heard this were rightfully horrified and very upset (as they should have been) and began to cry and get upset so much that the place the angel of the Lord was preaching was called 'Bokim' ( Hebrew for ‘Weepers’) and in honor of their God they offered sacrificed (possibly for their sin of disobedience):
Judges 2:4-5
“When the angel of the Lord had spoken these things to all the Israelites, the people wept aloud, and they called that place Bokim.[Hebrew for ‘weepers.’]…There they offered sacrifices to the Lord.”
But they still allowed the Canaanites to stay in Israel as slaves!!! And even began to marry in with Canaanites like God forbid them to do and had mixed race children from them!
Judges 2:3:5-6
“The Israelites lived among the Canaanites, Hittites, Amorites, Perizzites, Hivites and Jebusites. They took their daughters in marriage and gave their own daughters to their sons,…”
Just like God said, these Canaanites and their false gods became a trap for the Israelites as their Canaanite partners tempted them to honor, serve, and worship their false gods: especially the king of Canaanite gods Baal and they eventually began to completely convert to the Canaanite religions of their canaanite slaves and completely abandoned worshiping their God to worship Baal and Asherath!
Judges 2:11-17
“Then the Israelites did evil…[and]…served the Baals. They forsook the Lord, the God of their ancestors, who had brought them out of Egypt. They followed and worshiped various gods of the peoples around them….They quickly turned from the ways of their ancestors, who had been obedient to the Lord’s commands.”
Only a single generation from loyal Israelites committed to keeping God’s special covenant with them after their parents broke the brand-new covenant, were once again not only breaking God’s command but his #1 commandment for them:
DO NOT worship another God!
This of course made him angry as he became jealous of Israel’s betrayal and breaking of his covenant and their adoration of these other false non-existent Canaanite gods who’s people he pretty much destroyed!
Judges 2:11-13
“Then the Israelites did evil in the eyes of the Lord…They aroused the Lord’s anger because they forsaked him and served Baal and the Ashtoreths.”
Because they disobeyed his command to kill the rest of the Canaanites left in their land and also allowed themselves to become corrupt by intermarrying with these pagan Canaanites and breaking the core law of his holy covenant by worshiping other false Canaanite gods with their Canaanite partners, He became very angry and for breaking his covenant after they’re parents/grandparents promised to obey it. He began to curse them by letting them be invaded and conquered by neighboring nations:
Judges 2:14
”In his anger against Israel the Lord gave them into the hands of raiders…”
These enemies were either the remaining Canaanites or neighboring nations who, all of a sudden, were able to defeat the formerly unconquerable Israelite army: When the army tried to fight back against these invaders, they couldn’t win against these enemies and ended up being defeated:
Judges 2:15
“...Whenever Israel went out to fight, the hand of the Lord was against them to defeat them, just as he had sworn to them.”
Once they were defeated, these invaders stole and pillaged their newly found cities and took their goods/food and oppressed them:
Judges 2:14
”…[the].. raiders…plundered them.”
So, for months (possibly even years) the Israelites were oppressed and even enslaved to these invaders and began to get horribly upset and cry:
Judges 2:15-18
“They were in great distress….groaning under those who oppressed and afflicted them.”
Because they were soo upset, God felt sorry for them and had mercy on them as his people and began to stop their oppression:
Judges 2:16-18
“Then the…Lord relented because of their groaning under those who oppressed and afflicted them.…”
Like he stopped their oppression by their Egyptian oppressors, to save them from their oppression, he once again choose one of their fellow Israelites to not only save them and help them fight these invaders from their land but also to judge them for their sin of breaking the covenant and lead them back to serving their God only: this chosen leader of God for his people Israel was known as a judge:
Judges 2:18
“…the Lord raised up a judge for them,…”
Through this chosen Judge, God helped him get Israel’s army together and they fought off the invaders and drove them out of Israel, thus freeing Israel once again:
Judges 2:18
“… he was with the judge and saved them out of the hands of their enemies…”
Once this Judge saved them from these invaders, he began to judge Israel for sinning by worshiping these false Canaanite gods and tried to teach them to obey their God and worship and serve him alone, but Israel refused to go back to worshiping their God they wanted to continue to worship Baal and Ashtoreth as their Canaanite partners (and now children) desired:
Judges 2:17
”Yet they would not listen to their judge… but prostituted themselves to other gods and worshiped them.”
Despite this rebellion, God allow their enemies to be defeated and kept away from Israel as long as this judge lived: because it seemed his leadership kept at least some Israelites from completely worshiping other gods:
Judges 2:18
“…as long as the judge lived;…[he]… saved them out of the hands of these raiders.”
But when this judge finally died, this rebellious generation of Israelites completely turned back to worshiping pagan gods of the local foreign nations and became even worse than the former generation before they were saved!
Judges 2:19
“But when the judge died, the people returned to ways even more corrupt than those of their ancestors, following other gods and serving and worshiping them.”
But once again, God got angry at their stubborn refusal and cursed them with more invasion, but when they began to suffer from the oppression of their conquerors and got very upset and cried God had mercy on them and chose one of them to be a judge to free and lead Israel back to him, however each time a Judge freed them from their rightfully deserved curse the majority of them refused to serve God as he fully desired and each time when the judge died they returned completely to worshiping these false pagan gods as if nothing ever happened!
Judges 2:19
"They refused to give up their evil practices and stubborn ways."
After a couple of generations of doing this with Israel, God had had enough with their stubbornness; they had once again broken his covenant just like their evil ancestors, but instead of killing them all, he vowed from now on he would never help Israel run out the remaining Canaanite nations ever again (let alone any other nation in their unconquered land) but purposefully keep them there as a curse for their stubbornness and in order to test them to see if they would ever fully love him/his covenant with them enough to ever return back to him completely as a nation with all the pagan nations around and in their land testing their loyalty, or just continue to worship false gods with all the other nations and be cursed some more until they completely were destroyed from their land:
Judges 2:20-22
“Therefore the Lord was very angry with Israel and said, ‘Because this nation has violated the covenant I ordained for their ancestors and has not listened to me, I will no longer drive out before them any of the nations Joshua left when he died. I will use them to test Israel and see whether they will keep the way of the Lord and walk in it as their ancestors did.’ ”
So any remaining Canaanite nations within Israel (who were probably getting very intermarried with Israel at this point) and all other unconquered nations in their land would remain until further notice: They would now become a permanent stumbling block/curse for Israel to test Israel’s love for their God in the face of pagan temptations.
So for 100's of years this cycle of being saved from their neighboring enemies and (partially) returning to obey their God and his laws only (for most) to return to worshiping pagan Canaanite gods even more, happened over and over again and each time a judge died they got a little worser and more corrupt from the paganism than the former generation of Israelites were: It seems Israel was losing love for their God and giving in to the pagan temptations around them: it seems Israel was quickly failing this test of loyalty. After 100's of years later something tragic would even happen to the descendants of Aaron: the present high priest of Israel and his sons helping him at the temple of God in Shiloh that would shock all of corrupted Israel (coming soon).