WarpMyMind

It's good to take the time to pray with him. But people do by nature that which they feel compelled to do. In other words if begging has fed / helped him in the past, his conditioning is to do what has worked before. A better method is to help him on his feet. Perhaps.... put him in touch with a church where he can eat regularly ( food handled ) find a place where he's warm and safe each night ( shelter handled ) take him to the thrift store and buy him some clothes and toiletries IE: shaver, brush / comb, etc... (personal care handled). Continue to pray with him, talk about what he can do to get back on his feet, remind him that God hasn't forgotten him and he's still valuable (hope handled).
These are simply suggestions but bottom line, he needs a friend, be that friend.
Good Luck to both of you.