Namechanger.
I have a younger (21-y-o) brother and an older sister. My father is kind but has a new family, we lost our mother when we were quite young. Because of this, DBro has always been a bit spoilt as we all (me included) tried to make up for the sadness he'd experienced. He is a lovely guy that is easy to talk to, very charming, we are all quite close.
About 3 years ago, we discovered that he had been routinely stealing from my father. A few quid here and there turned into raiding the savings box for alcohol and cigarette, and possibly cocaine money. We were told he always bought rounds of drinks for his mates (he found it difficult socially, and I think he was trying to buy friends.) The amount he stole is in the thousands, over a two-year period.
We were devastated, because this seemed completely out of character for the personable young man we knew. But his reaction was even worse. He ran away to friends' houses, posted on facebook about how his family were treating him like shit, ignored calls by us. He made it as though it was our fault for finding out. He has never really, properly apologized- He said sorry under duress but it was so we'd leave him alone.
He then went to uni. Seemed to be getting better- We started building bridges. Then, on a trip home, he stole £200 from my father's new GF. :(
He said sorry for this too, but again, acted as if it was outrageous that he was being forced to apologize.
He dropped out of uni, got 2 jobs. Goes out a lot, has a very active social life. We have made up, but have never talked about his stealing. I thought, what with the two jobs, he was doing well and being self sufficient.
This morning, I got an email from my father, who is on holiday abroad. He was asking me or my sister to transfer £100 to DBro's bank account because he couldn't do it from abroad- DBro needs it by tomorrow morning for rent. Turns out this is a regular occurance- Dad lends him money and he pays it back little by little in installments (he now owes my father quite a lot). The money, apparently, will be paid back in August. DSis has a foreign account and cannot transfer.
I have just been paid and have the money. But I don't know if I should bail him out. A part of me thinks he shouldn't expect, after everything, that his family will save him every time. He smokes, he drinks, he spends a fortune on himself... And I don;t know if it's really doing him any favours to make him so dependent. OTOH, Dfather and DSis will think I'm a total bitch if I don't. And a part of me feels so sad for the shitty childhood he had.
What should I do?