Sooner or later there has to be success. Sounds like they have never done their part to prepare him so that he might have some successes. I guess my question to you is this. But he just can't seem to get on a positive path in school. Any input or ideas from you would be greatly appreciated.
Sports are great, all that some kids find as a source of some success.
Think of minority kids in football, basketball, boxing. That they lag academically, vocationally, economically is the fault of the school, not their fault. With no awareness of you race, ethnicity, I suspect the schools have failed your son educationally. At 14, with failure ingrained the hour is late. There is no way around it.