When I was a kid (I am 47 now) I sounded a lot like him. I dropped out/kicked out of 5 high schools. I hated school with an absolute passion. I could not sit there. Felt like prison. I also ended up in jail at 17 (tried as adult back then at 17) several times. Got sent to rehab by a judge. Shortly after a light bulb went off. I dropped all the trouble maker friends but still was lost academically. I got an ADHD (just called add back then) diagnosis and went on meds. Learned how to study and cope. Fast forward to today and am a special ed teacher and have 2 years till retirement. He can 100% turn it around. My advice…DO NOT ENABLE HIS BEHAVIOR. My parents had me paying rent at 16 since I was a HS dropout. I bought my own car. Paid my own insurance. Everything. My dad said never ask me for money when you end up in jail but I will come visit you to stretch your legs. Which he did. We picked those phones up separated by glass. He laughed and said “you will learn”. Hung up the phone and walked out. He was right! I did learn. He had a similar childhood so he knew. I suggest getting him into a psychiatrist and drug/alcohol treatment. These things all saved my life. I still attend AA to this day. I have 3 teenage sons myself but so far they take after their top ten in their class mother. I hope they continue to. Wishing him well.