In reply to Ciro:
> If he's suffering low self-esteem and stealing to anesthatise with drink and drugs, or to show off to his mates that he's the cool guy with all the toys to cover his inadequacy, hammering him hard is likely to chip away further at that self esteem and perpetuate the self-destructive behaviour.
That's a very good point.
> Same goes for excessive "look at what this means to the kids holidays" guilt tripping... unless he's a sociapath, deep down he's already beating himself up for his behaviour, despite continuing to do it.
> It has to be clear that he's done wrong, but the solution has to be balanced and offer a path to redemption. As Neil says rebuilding trust is important so where, for example taking the car away for a month does nothing much other than breed resentment, taking the car away or limiting the hours of use until some money has been paid back, or if that's going to be difficult perhaps does work around the house (painting and decorating, building sheds... constructive stuff that he can look at in future and be proud of) will allow him to feel he's atoning for his behaviour and emerge with some self-esteem.
That's much better than my idea.