What if my son never wins?

That could happen.

It’s your job to teach him to do his best and not get too discouraged. There are “beginner” tournaments where only kids who are new to wrestling are allowed to compete. He should start there, but there is no guarantee he will win there either. The other difference in “beginner” tournaments is that they are “round robin” format instead of brackets. Kids are grouped by 5 and everyone wrestles each other. It means he stands a better chance to win a bout and he won’t be wrestling kids with years of experience.