Thanks, everyone.
I feel bad and love him but it is really upsetting.
I, too, struggle with depression and anxiety but, even when I was going through a crushing divorce I coped without any help from family and maintained my career. I also, somehow, was able to stop my toxic drinking patterns at this lowest point in my life. I have pointed him to this site and offered to just meet him for lunch but it seems he mostly only contacts me when he's in need of cash which is also hurtful. Three attempts at contacting me in three days for money when I hadn't heard from him in ages.
I am frustrated as I really think he could work and pull his life together. He is so privileged compared to so many out there. I do not begrudge those who need assistance but I think he could have done things in the past ten years to get himself out of this rut, especially stop drinking.
He said something on one of the voicemails about the dates of "getting paid" and how he only has five dollars until February. Where did his money go especially if my mother is paying for his groceries? It makes no sense; it's not like he spent his money on 'gifts'.