If it ends up not being infected, I would consider a blocked eustachian tube. It was pain that would drop me to my knees. Felt like it was in my ear, but it wasn’t really.
Best way I found to take care of it was massaging from where the ear meets the jaw, down the neck, across the top of the shoulder.
There are also some jaw movement exercises he might be able to do that help it drain.
Ear pain is no fun. Sorry he’s going through that.