After he lost his job, I negotiated a settlement for him and made him pay his back taxes out of the funds he received (in addition to paying an accountant to file three years of returns). He blew through the rest of the money. (In fairness, he is no longer gambling — just paying bills.) He has exhausted his unemployment, hasn’t paid his rent and is ignoring the information I send on programs that could help him afford rent and health insurance (which he doesn’t have). My family has rental housing some distance from his home — which at least he wouldn’t get kicked out of — but he has rejected the idea of moving there. I have clients who have offered him jobs in his field and he has declined.