Hello. I believe I can be of help to you with this issue.
No single diagnosis likely captures these problems. Some hypotheses would include:
Antisocial Personality Disorder, PLUS Major Depressive Disorder
or Dysthymic Disorder. One cannot of course, offer a diagnosis in a question-answer format such as this, without a proper evaluation.
I suspect your son has had many other diagnoses over the years
such as oppositional defiant disorder as a child, perhaps bipolar
disorder and ADHD. If your son is willing, he needs to be in long-term, individual and/or group psychotherapy, and family therapy would be a good thing if he is living at home. For individual therapy, I would suggest a particular modality of therapy called dialectical behavior therapy.
What do you think? He may also do best in a structured, residential living setting that offers group therapy or a therapeutic community, but these are hard to find unless the individual primarily has a drug or alcohol problem, or significant deficits in intellectual functioning.