‘Nothing is ever his fault, everyone is out to get him.’ Our brother inherited our late mother’s home and it was repossessed. He’s now in prison — do I send him money?

Dear Moneyist,

I am not sure who to turn to. I have had no luck finding a support group to help me determine what to do. My brother has been in and out of prison most of his adult life. I don’t really know the specifics of each term and I don’t really want to know. He is currently serving an eight-year sentence in Tucson.

Our mom died from cancer in 2006. When he was out for a brief time, he cared for her while she was dying and subsequently inherited her home.This was a decision made by my other brother and I at the time of her death.This was a free house. No mortgage or bills of any kind. He lost our mother’s property after obtaining a high-interest mortgage so he could buy a motorcycle, which he also lost as a result of an accident.

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When he re-offended, he was living with his long-time girlfriend in the home. After he was incarcerated, she took everything from the home and left. He lost the house at that time. So he literally has nothing. Nothing is ever his fault, everyone is out to get him. Or so he says.

I have been in contact with him the entire time he has been in prison during this last stint. He gets moved around a lot. I have given him $100 every month through the prison system, to buy toiletries and such. He was slated to be released right before Christmas. However, his sentenced was extended through, he said, no fault of his own — of course — and he was moved to a maximum-security yard. He said that county police will arrest him upon his release for some infraction of contraband while he was in a facility. I am his only hope.

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Do I continue to support him financially? He said that he has no one except for me and is talking like he may self-harm. We do have one crazy old aunt that says she will take him in after he is released, but who knows if that will happen. Any help is appreciated.

Tired Sister

Dear Tired,

You have given your brother so many opportunities to get back on his feet and he didn’t take them. He sold the house you and your brother agreed to give him. It was — strictly speaking — part of your inheritance too. There does not seem to be any accountability or self-awareness on his part. It’s time to step back. There is sometimes a fine line between helping someone and enabling them, and I’m afraid everything that could be done to help him has been done. Take heart in that.

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There comes a time when enough is enough. You gave him money to buy extras in the prison commissary. But you say his latest infraction related to contraband. Is there a way of giving him money that could be used solely for the purpose for which it is intended, so he is not tempted to spend it in ways that might contribute to any addiction he is suffering from and/or put temptation in his way? Even the cost of prison phone calls can be exorbitant and vary wildly from state-to-state. 

Can you afford to give him $100 every month? If not, don’t do it. If you can, be smart about how you spend it. I don’t believe you should cut off all contact and/or support. But you do need to put your own needs first (for a change). He may lean on you because you are one of the few people he has in the world and/or he may know how to manipulate you and pull at your heart strings. I know one thing: You can’t live your life by being of service to someone who is unwilling to help himself. 

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He may have mental-health issues underlying his criminal and/or financially erratic behavior. If that’s what’s happening here, you can help make sure he gets the help he needs when he is released. Is he in the throes of a decades-long addiction to drugs and/or alcohol? In order to get better he must want to get better — and face up to his own role in creating the chaos around him. If that is the case and I certainly hope it’s not, you are not his only hope. He is his only hope now.

Do you have questions about inheritance, tipping, weddings, family feuds, friends or any tricky issues relating to manners and money? Send them to MarketWatch’s Moneyist and please include the state where you live (no full names will be used).

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