She is an adult now and I think it might be time to let her find her own way - even if she gets in a whole heap of trouble along the way. I think he should certainly be her soft place to fall when she needs the support but you're right - she needs to realise for herself that this life is only going to end in heartbreak for her if she continues. My own brother was headed down a simliar parth - a juvenille record as long as your arm and even a few minor convictions for things as an adult. As a teen he barely escaped going to jail a few times and it was only that he got lucky with the judges he had. He did grow out of a lot of the behaviours that were getting him into trouble as a teen and he's not been too bad the past few years. So while his life is far from perfect, it is also far, far different to what it could have been