Judges 1:10–15 is a story that is actually taken right out of the middle of Joshua 15:15–19. There, Joshua is alive, yet Judges 1:1 indicates he is dead. This is further evidence that the book of Judges is not organized from a strictly chronological perspective.
10 And Judah went against the Canaanites who lived in Hebron (now the name of Hebron was formerly Kiriath-arba), and they defeated Sheshai and Ahiman and Talmai.