I have a brother quite similar to this. I was digging through some old papers I had saved from when I was in my 20s and found a contract that I made my brother sign for a car I "sold" him for about $3500. I set up a payment plan and everything. He made one payment and then nothing. He took and took and always got in trouble and eventually turned into an alcoholic and got into rehab and cleaned up his act and got married but for about 20 years he just was exactly like your brother. Eventually my brother found Trump and then I truly lost him. I hardly speak to him anymore. We were so close at one time. It's really sad. About 3 years after my brother signed that contract with me he totaled that car he said trying to avoid a deer at 2am but we all knew he was probably drunk as a skunk. There was a burrito all over the inside of the window so I really doubt him. He went into the air force and got kicked out after about a year. What a wreck of a life.