What does Judges 2:2 mean?

The Lord is speaking to Israel in the form of the angel of the Lord. This is some material appearance of God, possibly a pre-incarnate presence of God the Son. He has reminded them of His faithfulness and provision for them, along with His promise to never break His covenant with them (Judges 2:1). Now, though, the Lord describes Israel's side of their covenant agreement—which the people have broken.

God clearly told Israel not to integrate into the people of the land (Exodus 23:32–33). Instead of letting the Canaanites stay, Israel was to break down their altars to false and foreign gods. Part of God's reason for sending Israel into the land was to judge the wickedness of the Canaanites in the worship of their false gods (Deuteronomy 7:1–5; 9:4–5).

In direct disobedience to this, the Israelites had made covenants with some of the Canaanites. They let them stay in exchange for help or slavery. They had left pagan altars standing. They had not acted with the Lord's help to drive them from the land. This is exactly what God wanted to avoid when His people entered the Promised Land (Deuteronomy 20:16–18). Israel has not obeyed the overt commands of their God. In the following verse, God will tell the people what they have done and what their disobedience has cost them (Judges 2:3).