Reply to Family member “retires” but expects me to pay for all the extra expenses

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[quote=Anonymous][quote=Anonymous]OP here: If I met my brother as an adult, of course I would hesitate to get involved. But it is family. I thought that he would get a job and move on—that it would be a short period. Instead it has been 3 YEARS, really 5 years since Dad got sick. Now that I can think clearly, having processed my dad’s death and brother’s relationship to dad’s money – he had access, obviously he took a big slice for himself. How else to live for 3 years without working and still have the benefits of middle class life? He does not have a pension/ savings etc. Now the money has run out. (There were several asides/ oblique references to this that I did not understand while dealing with my grief and my DHs decline) It has been a busy 3 years for us, dealing with the financial aspects of a forced retirement.

Every conversations is about how poor he is and how Dad should have left him more. As for the wife – she thought that she married rich – and considering her poverty and no green card, she did. Now she has it, has half of his assets, she and her four kids are exploring other options.  Since her teenage DD is now pregnant, citizenship problems are considerably relieved for her family. 
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I'll be honest OP, I don't understand why you went along with this.  Did it occur to you that if you never actually talked to your brother about what his plans were or when/how he planned to start earning money again, then you absolutely enabled this situation you're now in where he just expects you to pay because you have been for 5 years?  As well as him milking your dad's estate.

I'm NOT saying I think you should keep paying, absolutely not.  You should have cut him off ages ago.  But my guess is you have trouble having these difficult, direct conversations.  If so, you should seek help in how not only to have the conversation with him, but how to hold your ground.  Entitled, lazy relatives can be very mean, cunning, manipulative or other negative ways when they see what they took for granted is threatened.  If you already have trouble being direct with your brother, make sure you're ready to stand firm if it gets nasty from him.

You have to look out for your own family and not back down.  If you can do it on your own, great.  If you can't, seek help of a counselor or best friend or anyone you trust who can help you work through what it will take for you to be clear about your own family's needs, and also to understand that you are not helping your brother, you're enabling a horrible laziness and teenage-like entitlement by him not having to grow up and figure out how to support himself, since he is an able-bodied adult who has had it very easy for 5 years.[/quote]

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