From Commissary Debt To Family Guilt — This Redditor’s Brother Called Collect Again

For nearly two decades, the Reddit user u/Jonesyajones‘s older brother R has treated prison like a revolving door with loyalty points. At 37, R has perfected a chaotic post-release routine that would be funny if it weren’t so exhausting.

Day one usually starts sweetly enough, with Mom picking him up, buying him a phone, and setting him up somewhere temporary while he “waits for rehab.” The second she leaves, he vanishes for 24 to 48 hours, and the phone mysteriously disappears—often sold for drug money or traded during a stolen car adventure.

By day three or four, R resurfaces like clockwork. The high has worn off, the debts are piling up, and he needs Mom to either cover what he owes or rescue him from wherever he’s landed.

Within a week, he’s gone again, and the family waits for the inevitable call that he’s been arrested for stealing another car. This cycle has repeated itself four or five times, even after the family tried moving him away from his usual crowd.

After R’s most recent arrest six months ago, the OP finally blocked his prison number for his own sanity. Peace lasted—until a new prison number popped up on his phone.

R claimed he’d racked up serious debt inside for borrowed commissary items and now feared retaliation. The OP refused to pay, saying their relationship was already strained and he wouldn’t fix another self-made crisis.

R argued that the family should help no matter what. The OP blocked the new number too, and while Mom supports the decision, guilt is still lingering like an unwanted collect call.

This cycle has repeated itself four or five times, even after the family tried moving him away from his usual crowd.

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Here’s the original post by Reddit user u/Jonesyajones.

I 31M have a brother 37M(I’ll call him R) that for the better part of the last 2 decades has been in and out of jail. R has a drug and gambling addictions that more or less feeds off each other. My brother for lack of better words is a crappy criminal. He does the same routine every time he gets out of prison to the point it’s almost comical. Day 1. He gets out of jail and hangs out with Mom. She usually gets him a phone, food, temporary place to stay while he waits for a spot in rehab. Once she leaves he goes missing for 24-48 hours to get drugs. Usually by selling his phone or stealing a car. Day 3 or 4. He reaches out after his high is over to either have mom attempt to pay off some drug debt/escorts/gambling or pick him up from a crack house and or take him back to his current residence. By end of week his gone missing again and we usually just wait for him to get picked up my police for stealing a car. This has been the case for the last 4-5 times he’s gotten out of prison. We’ve moved him out of his city so he couldn’t be in contact with his dealers but he chooses to go back or find new people to aid in his addiction. So after his most recent arrest (6 months ago) I decided to block his prison # for peace of mind. At least Until R decided to do better for himself. Yesterday I get a call from a different prison # and regrettably answer. R tells me he accrued a massive prison debt from borrowing snacks and other commissary items (prison no no #1 don’t borrow shit) and the debt has doubled and tripled. Now multiple people in his unit are telling him he needs to pay up or else things are about to get real difficult. I flat out refused. Saying we already don’t have a great relationship due to his actions and I refuse to help in a problem he created for himself and likely is drug related. My brother feels like family should help regardless of circumstance and that I’m letting my emotions over how I feel about him cloud my judgment as he is in dire need of help. I blocked his number and called our Mom about the situation and she supports my decision but I do feel somewhat guilty even though I know he put this problem on himself. So AITA?

Let's see how the Reddit community reacted.

Deleted user

He clearly needs to learn the hard way.

TouchoMySpaghetto

You need to stop bailing him out.

AfternoonGullible983

If you clear his debts, he'll only create more.

DanFante1972X

He needs to be responsible for his own actions.

Cannabis-aficionado

NTA.

Killer-Barbie

He'll never learn if you keep enabling him.

subsailor1968

Nope, he's an adult.

Individualchaotin

Time for him to take care of himself.

willf6763

100% buying drugs and gambling.

Deleted user

He needs to learn somehow.

SuperLoris

Time for him to man up and do his time.

bigben7102

You need to protect yourself.

No_Detective_715

In the end, the OP isn’t questioning whether his brother is in trouble — he knows he is. The real question is whether love means constantly cleaning up the mess or finally stepping back and letting consequences do what years of bailouts couldn’t.