2- Judges were unlikely leaders
This video explains a bit of who the judges were. It mentions that the book is full of stories that are violent and brutal. (The video doesn't show any of that.)There were both men and women judges and most of them were pretty tough. But they were far from perfect. So why would God choose less than perfect people to lead his people?
If we think about the judges like Superheroes, it may help us understand a little better. Most Superheroes have major flaws. Yet they are the good guys that we want around when everything falls apart.
So what happened? Well, each flawed superhero eventually fell for the biggest temptation ever. Putting themselves or other gods ahead of the one true God. Breaking the covenant with God. God said "You shall have no other gods, you shall worship no idols..." but the superheroes and the Israelites couldn't stay true to their part of the covenant.
Follow the covenant and good things happen. Ignore the covenant and bad things happen.