Reddit Stories - Invested a large sum of money SUPPORTING my sibling STRUGGLING with ADDICTION, which

Episode Date: November 3, 2025

#redditstories #askreddit #aita #family #addiction #support #money #struggleSummary: Invested a large sum of money supporting my sibling struggling with addiction, which led to a heated debate on AITA subreddit.Tags: redditstories, askreddit, reddit, aita, tifu, family, addiction, support, money, struggle, debate, relationship, personal finance, ethics, moral dilemma, controversial, advice, community, social media, online discussionBecome a supporter of this podcast: https://www.spreaker.com/podcast/reddit-stories--6237355/support.

I hope you enjoy this story. Invested a large sum of money supporting my sibling struggling with addiction, which involved funding rehabilitation programs on two occasions and offering free accommodation. However, he took my portable computer to purchase drugs and substances. Now he's in jail begging me to help one more time. I, 32M, have a younger brother, Tyler, 29M, who has struggled with drug addiction for the past five years. To give some background, I've always tried to be a supportive older brother. Growing up, Tyler and I were close. We come from a middle-class family with loving parents,

and neither of us had a rough childhood or anything like that. Tyler was actually a smart, outgoing kid and later a friendly, funny teenager. He had a ton of potential, good grades when he applied himself, and a knack for art and graphic design. Unfortunately, in his his early 20s he fell in with a bad crowd and started using drugs. What began as occasional partying escalated into a full-blown addiction that has consumed the last five years of his life. During those five years, I've done everything I could think of to help Tyler get clean and get his life together. I haven't just been a bystander, I've actively tried to support him time and time again, often at great personal cost. To illustrate, here are some of the major ways I've

tried to help my brother. One, paid for rehab, twice, I shelled out thousands of dollars for two separate stints and rehabilitation facilities for Tyler. The first time was about four years ago when his addiction became obvious and he agreed to get help. He stayed through the program, about 30 days, and got clean for a short while, but relapsed not long after. A couple years later, I paid for a second rehab stay when things got really bad again. Unfortunately, that attempt also failed. He finished the program, but relapsed within months. 2. Provided housing, I let Tyler live with me rent-free on multiple occasions.

Whenever he was doing particularly poorly or had nowhere to go, I opened my home to him. I thought a stable environment might help. I gave him a room, bought groceries, and didn't charge him a dime. Each time, it ended with him either sneaking off to get high or, in a few instances, bringing drugs into my home. I eventually had to kick him out more than once when I found paraphernalia in the bathroom or when he came home obviously high despite promising he wouldn't use under my roof. Three, offered jobs and financial support, I've helped Tyler get jobs at my workplace,

I run a small business, and through friends of mine. I basically handed him employment opportunities, hoping that having a job would give him structure and purpose. Each time, he either stopped showing up or behaved so unreliably that he got fired. Alongside that, I've loaned him money, which was rarely paid back, for things like paying off minor debts, getting his car fixed, and covering court fines from drug-related incidents. I did this hoping to remove some of the excuses he might use to justify continuing his lifestyle. Overall, I've been there for him countless times, driving him to support group meetings, talking him through depressive episodes, picking him up from sketchy neighborhoods in the middle of the night when he was strung out, you name it.

Emotionally and financially, I've gone above and beyond for Tyler. My hope was that if I kept showing him he had support and a pathway out, eventually it would stick. I deeply love my brother, but his addiction has put me through the ringer. It's exhausting and heartbreaking to watch someone. repeatedly self-destruct despite all the help you extend. There have been many low points over the years, but the most recent incident really broke my trust completely.

About a month ago, Tyler did something that hurt me profoundly, he stole my laptop and pawned it to get money for drugs. This happened while I was at work. I came home in the evening and my laptop, which I use for both personal and work matters, was missing. At first I thought I had misplaced it, but pretty quickly I occurred. piece together what likely happened. I confronted Tyler, who was crashing at my place at the time, yet again, and after some initial denials, he admitted he took it and sold it because he was

desperate for cash to buy pills. I was furious and felt utterly betrayed. That laptop had important files and personal info on it. I told him to get out of my house immediately. I was done, I said I couldn't have him under my roof after that level of disrespect and violation of trust. He left, and honestly, I wasn't even sure where he went that night. I just knew I needed him out of my space. Not long after the laptop incident, Tyler's downward spiral continued and caught up with him in a big way. He ended up getting arrested for drug possession a couple of weeks later. It wasn't his first run in with the law, but it's the most serious so far and it looks like he might be facing real consequences this time.

In any case, he's currently in jail on those possession charges. From jail, Tyler reached out to me, and to our parents, asking for help. Specifically, he wants me to pay $8,000 for him to enter a particular private rehab program. According to him, the court is willing to release him to attend rehab if he has a guaranteed spot. The program he's talking about is a 90-day inpatient facility. He claims that this time will be different because he's finally hit rock bottom and is truly ready to get clean for good. He sounds scared and desperate, saying he knows this is his last chance to turn his life around. I have very mixed feelings.

I honestly do not trust him when he says this time is different because I've heard that before. He has claimed to hit rock bottom multiple times, only to go back to using as soon as things stabilized or the pressure was off. It's a vicious cycle, he promises change, I, or my parents, relent and help him, he relapses, and we're back to square one. Meanwhile, I'm out another chunk of money or have endured more chaos in my life. The $8,000 he's asking for is not a trivial amount for me. I do have some savings and I could technically come up with the money, but it would mean delaying other financial goals I've been saving for a house-down payment, among other things.

More than the money, it's the principal and the emotional toll. Each time I've paid for rehab or helped him out, I get my hopes up and then end up crushed and angry when he falls back into old habits. It has taken a huge emotional toll on me. Our parents are also involved in this. They cannot afford the rehab costs themselves, they're nearing retirement and don't have that kind of money, so they're pressuring me to pay,

saying that we can't just abandon Tyler and that this might be the chance that finally sticks. My mom, especially, is pleading with me, she's terrified he'll die if we don't help. Dad is more reserved but he also feels we should try to support Tyler one more time, given how serious the situation is. I understand their fear, I'm scared too, but I also feel resentful that the expectation always falls on me to foot the bill and clean up the mess. They haven't spent the kind of money I have on this, though of course they've dealt with the emotional burden. It's like they view it as my duty as the older brother, since I'm more financially stable, to keep rescuing Tyler. I've told them, and Tyler, that I'm extremely

reluctant. I basically said I do not want to pay for another rehab stay because the last two times didn't work and he even stole for me most recently to fuel his habit. I said I believe I've done more than enough and at some point Tyler has to help himself. That was met with various reactions, my mother cried, my father said he understands but disagrees, and Tyler has been sending me letters from jail, plus phone calls when he can, trying to convince me that this time will be different. In his messages, he acknowledges he screwed up horribly by stealing from me and says he regrets it deeply. He insists that being in jail has opened his eyes, that he never wants to end up here again, and that if I help fund this rehab placement, he will finally straighten out. It's a lot of emotional

pressure, honestly. I'm really torn. If I don't pay, he might just sit in jail or eventually get released back into the same environment with no structure, and then he could very well end up overdosing or worse. I fear that scenario. But if I do pay, I risk being out a large sum of money for potentially nothing if he drops out or relapses yet again. It feels like a lose-lose, either I feel guilty for possibly allowing my brother to come to harm by refusing to help, or I potentially enable him further and take another financial hit for no result. So that's where things stand. I'm leaning towards not giving him the money this time,

simply because I feel I have to draw the line somewhere. I'm emotionally at the end of my rope and I don't have it in me to go through yet another cycle of false hope and disappointment. I also don't like that I'm being expected to sacrifice my own future financials. security for something that has a high chance of being wasted again. Still, it's a very hard decision and I feel awful about it. That's why I'm here. I need some outside perspective. Am I the asshole for not helping my brother pay for rehab after he stole for me to buy drugs?

Update 1, about one week later. First, I want to thank everyone who commented on my original post. I read all the responses and it was enlightening, and emotionally tough to see what people had to say. The majority of you told me I was NTA, not the asshole, and that I had done more than enough for Tyler. A lot of you pointed out that continuing to bail him out might just enable him to keep using without facing the full consequences. Some also encouraged me to consider one last effort if I saw true remorse, but only with strong boundaries in place to protect myself. It gave me a lot to think about. After wrestling with the decision, I decided

to at least go see Tyler in person at the county jail before making a final call. I figured I owed it to myself, and to him, maybe, to see his condition and gauge how sincere he really was. So a couple of days after my post, I visited him during visiting hours. Seeing my brother in jail, in an orange jumpsuit behind Plexiglass, was pretty sad. We had to talk through a phone handset across a glass partition. He looked tired, thinner, and he looked tired, and genuinely miserable. When he saw me, his eyes filled with tears almost immediately. I've seen Tyler cry before, often in manipulative or withdrawal situations, but this felt

different, he looked broken. Our conversation was emotional but fairly calm. Tyler started by apologizing profusely. He said, I'm so sorry for everything, for stealing your laptop, for lying, for all the pain I've caused. He actually broke down sobbing at one point, saying he hates who he's become. I tried to stay neutral and just listen without promising anything. I told him I was very hurt and angry about what he did, and that I've lost a lot of trust in him over the years.

He said he understood completely and that I have every right to feel that way. I asked him why he thinks this time will be different. I needed to hear his reasoning. He took a moment to compose himself and then, explained that being in jail has been a huge wake-up call. According to him, something really traumatic happened on his first night there, his cellmate overdosed and died right next to him. Apparently the guy had smuggled in drugs or had taken a lot before being arrested, and he went into cardiac arrest overnight, I was stunned hearing this.

Tyler said watching someone literally die from drugs, in a filthy jail cell, absolutely terrified him. It was like looking at his own future if he didn't change. He then detailed a plan he's been thinking about. He told me that if he can get into this 90-day rehab, he's determined to stick with it fully. After rehab, he wants to go into a sober living house or transitional program for a while to slowly adjust back to normal life while staying clean. He said he's willing to attend daily N.A. Narcotics Anonymous, meetings, get a sponsor, go to individual therapy, basically whatever it takes. He even talked about maybe going back to school or getting a certification in graphic design once he's stable, because he remembered how much he used to love art.

Honestly, it was the most detailed and future-oriented plan I've ever heard from him. Usually in the past his promises were vague like I'll get a job or I'll stay clean, I swear, but this time he actually had steps in mind. I'll admit, sitting there hearing all this, my resolve was shaken. I had walked into the jail determined to stay firm and not get sucked in by what could be more empty promises. But the combination of seeing him so genuinely scared and remorseful, and hearing about the cellmate's overdose, a pretty extreme eye-opener, really hit me hard. He said more than once, that could have been me. If I keep going like this, it will be me. I don't want to die. That was the first time I'd heard him express such a blunt feeling.

fear of death and desire to live. My brother actually saying I don't want to die, I want to live, it struck me deeply. He also said, I know I've said all this before. But I swear this time is different. Something clicked. I'm done with this life. I'll prove it to you. Just please give me one more chance. He was pleading, but in a remorseful way, not an entitled way. I didn't make any promises right then. I told Tyler I was glad he was thinking seriously about his future and that I truly hoped he meant every word. Before I left, he asked me one more time to consider helping him get into the rehab. He said, no matter what you decide, I love you and I'm sorry for everything. Hearing that, along with him saying he doesn't want to die, really stuck with me.

It sounded sincere. And I left the jail feeling very conflicted and emotion. In the days following that visit, I had long talks with our parents and did a lot of soul searching. My mom was of course adamant that this was a turning point for Tyler and we had to help him get into that rehab. My dad was optimistic but said something like, if this doesn't do it, nothing will, implying that this truly is the last chance. I also reflected on the advice many of you gave. Some of you said to help him but with very clear conditions to avoid enabling, while other said it was time for tough love and to let him face the consequences on his own. Ultimately, I've come around to the idea of giving him what I truly believe is one final chance, but not blindly.

I'm going to have safeguards for my own sanity and to ensure he has some skin in the game. I haven't committed the money yet, but I've started looking into the rehab program he mentioned to verify its reputation and see if there are any payment plans or options. I also spoke to a lawyer friend about possibly drafting an agreement if I decide to pay, just to formalize things. I'll explain more in my next update once I firm everything up. I'll be honest, I'm still nervous that I might be making a mistake or setting myself up for more heartache. But if what Tyler told me is genuine, I know I would have a hard time forgiving myself if I didn't at least try to help him make good on it. I don't want to enable him, I want to help him help himself. There's a subtle difference there that I'm

trying to navigate. I'll update again soon when I have a concrete plan and decision. Update 2, another two weeks later, all right, I have made a decision and followed through with it, with some strict conditions attached. After carefully considering everything, and honestly losing a lot of sleep over it, I agreed to pay for the 90-day rehab program for Tyler, but I did so only after taking a number of precautions to protect myself and ensure Tyler is truly committed. First off, I didn't hand over any money directly to my brother, obviously. I contacted the rehab facility that Tyler wanted to go to and verified they would accept him as a patient coming straight from jail.

The $8,000 cost is indeed what they charge for a 90-day inpatient stay if paying out of pocket. I went ahead and paid the fee directly to the facility to secure his spot. This involved coordinating with the legal system as well. We arranged for Tyler to be released from jail into the custody of the rehab program as part of a deal with the court. The judge was on board with him going to treatment, but it had to be a reputable program and paid up front. It took some paperwork and phone calls, but we got it done. Crucially, before he left jail, I made Tyler sign a formal agreement with me. I actually drafted a document, with the help of my lawyer friend, that basically says the $8,000 for rehab is a

alone, not a gift. The agreement stipulates that if Tyler completes the full 90-day program and maintains sobriety, we can discuss a very lenient payback plan or maybe even forgiving some of it in the future. The primary goal is his recovery. However, if he fails to complete the program, for example, if he leaves early against advice or gets kicked out for breaking rules, or if he relapses soon after finishing, then he is required to pay back the entire $8,000 to me, within a certain time frame. In short, there will be concrete consequences if he flakes out. He didn't hesitate to sign it, he actually seemed eager, which I took as a positive sign. I know a contract can't guarantee good behavior, but it put our understanding in black and white and

made him accountable. About two weeks ago, Tyler was transferred straight from jail to the rehab facility. I went with him, since I had to handle intake paperwork as the payer. It was nice seeing him out of jail and into a treatment center, but I was cautiously hopeful. The rehab staff did a medical evaluation and intake interview while I was there. Before I left, Tyler gave me a big hug and thanked me about a dozen times. He promised me, again, that he wouldn't screw this up. I took that moment to gently remind him, Ty, this truly is the last time I can do this. If you bail or go back to using, I'm done.

No more chances, he said he understood completely and that it wouldn't come to that. In the first couple of weeks of his program, I had limited contact with him, which was expected, the facility has a policy of restricted phone access initially. I did get one brief phone call from him about a week in. He sounded okay, a bit low and tired, understandable while going through withdrawal and intense therapy, but he said he was sticking with it. He mentioned it was really hard, that some days in front of him. group therapy were tough, but he kept saying he was determined to see it through.

I also got a couple of progress updates from one of the counselors. Since I'm listed as an emergency contact and the one paying, Tyler signed a release allowing them to share general info with me. The counselor said that Tyler was participating in all the sessions and seemed motivated. She did caution that it's early, and many patients start strong than struggle, but so far he was doing well. That small bit of good news allowed me to sleep easier for a while. My parents were thrilled that Tyler was in rehab and doing all right initially. They've been much more at peace knowing he's off the streets and getting professional help. My mom has been sending him letters,

the rehab allows patients to receive mail, and he's written back a couple times, sounding thankful and committed. All of us were hopeful that maybe this time, with the scare he had in jail and a structured 90-day program, we'd finally see a lasting change. At this point, a couple of weeks into the rehab, things were on track. I was out $8,000, which definitely stings financially, but I tried to view it as an investment in getting my brother back healthy, which would be priceless. I had the written agreement for peace of mind, but honestly if he truly turned his life around I wouldn't care about the money. I allowed myself to imagine that by the end of the 90 days he could be a new man and our lives might finally stabilize. I was still prepared for

the possibility of failure. I'm a realist after all, but I had a bit of genuine hope. I'm posting this update now to let everyone know that, so far, things have been going okay. Tyler is in rehab, following the plan he promised, and I'm doing my best to support him without enabling him. I truly hoped I would have a positive report at the end of the 90 days. Update 3. One month after last update, well, here we are, and unfortunately the news isn't good. About a two months into the 90-day rehab, Tyler decided to leave the program early. To say I'm disappointed would be an understatement. I'm also angry, but more than anything I feel just utterly defeated by this whole thing.

Here's what happened, around the 47-day mark of his stay, approximately four to six weeks after my previous update, I got a call from one of the rehab staff informing me that Tyler had checked himself out AMA, against medical advice. In other words, he chose to leave the facility despite the counselors urging him to stay. Because this rehab isn't a locked detention center, it's a voluntary program, even if court supported, they couldn't legally keep him once he insisted on signing himself out. They tried to convince him to continue, but he was adamant and walked away from the program. I was floored when I got that call. Honestly, it blindsided me, by all accounts he had been doing reasonably well up to that point.

It took about a day, but he eventually called me, he must have borrowed a phone or something. He had left the rehab and ended up at a friend's place in that area. When I finally spoke to him, I asked him why on earth he would throw away this chance after everything we did to get him there. His reasoning, if you can call it that, was that the program. was too controlling and wasn't a good fit for him. He complained that the staff were too controlling and that he hated the strict rules and lack of privacy. He insisted he could stay clean on his own if he had more independence than the rehab allowed. In short, he was chafing

under the structure there and convinced himself he didn't need it. I was furious and also had this sinking feeling of here we go again. I told him that leaving rehab early was a huge breach of our agreement, both the personal promise he made and the literal contract he signed. I reminded him that, per our deal, he now technically owes me the entire $8,000, since he didn't complete the 90 days. He brushed that off with excuses, saying I'll pay you back, I told you I will, just give me time, and then quickly shifted to justifying his decision. He swore up and down that he hadn't relapsed, he claimed he just couldn't stand a particular program and that there are other ways to get clean. He kept saying, trust me, I know what I'm doing. I'm still serious about getting sober,

I just need to do it my own way. I was extremely skeptical, to put it mildly. He got a bit defensive when I expressed doubt and insisted he hadn't touched anything and wouldn't. Then came another request, he asked if I could give him a few hundred dollars for a sober living place, claiming he needed money for a deposit and first month's rent for a transitional housing arrangement. He said the friend's couch was only a temporary stop and that he wanted to move into a proper sober living house to continue recovery outside of inpatient rehab. He had basically nothing on him when he left, since he went to rehab straight from jail with just some clothes we gave him, so he said he needed help to make this move. This immediately set off alarm bells. Given that he just bailed on rehab,

I strongly suspected he might use the money for drugs. If he were really committed to sobriety, he wouldn't have left rehab in the first place. And handing him cash when he's vulnerable is basically like lighting it on fire. I told him flat out I wasn't giving him any money, especially after he reneged on our rehab agreement. I even said that if he had a specific sober living home lined up, he should give me the info and I would consider paying that place directly after verifying it,

but he couldn't provide any concrete details. He hemmed and hawed, then claimed the place he was looking at didn't take third-party payments, which sounded dubious. This made me even more certain that this was just about getting cash. He got angry and accused me of abandoning him when he was finally trying to fix his life. He said things like, so you're just going to turn your back on me now. I told him he was the one who walked out on the help that was provided. The argument went in circles until I finally said,

said I couldn't do this anymore, I was done, and I hung up. After that, I informed my parents about what happened. They were very upset, as you'd expect. My mom initially suggested maybe we find him a different program or help with that sober living place, but I put my foot down and refused. I told her it would be throwing good money after bad and that Tyler has to face the consequences now. My dad finally agreed that it's on Tyler to figure himself out. Both of them are extremely disappointed. As of now, Tyler is out of rehab and on his own. I suspect he's crashing with the same friend, likely not a great influence.

I haven't had any further contact with him since that phone blow up. I told him the door is open to talk if he wants to genuinely communicate, and not just ask for money, but he hasn't reached out again. Emotionally, I'm angry and heartbroken. I let myself hope, and he crushed it. This was the last big effort I had in me, and now there's nothing more I can do except let go and pray he figures it out. The $8,000 is gone, I doubt I'll ever see a cent of it.

Money can be recouped eventually. What's harder is accepting that I can't save my brother if he won't save himself. Right now, I'm focusing on not letting this destroy me too. I hate to end on such a down note, but that's reality at the moment. I'm basically bracing myself for whatever comes next with Tyler. I truly hope he somehow uses this as a lesson and gets clean on his own, but I'm not optimistic. I'll post another update if there are any major developments. Honestly, I hope the next update won't be a tragedy, but at this point it's out of my hands.

Update 4, 2 weeks after Update 3, this is a difficult update to write, but I think it will be the final one. About two weeks after Tyler left rehab, not long after my last update, he overdosed. We very nearly lost him. Here's what I know of the situation. Tyler drifted back to the same crowd and apparently relapsed not long after leaving rehab. One evening, he overdosed on what was likely opioids at a friend's house. The friend found him unresponsive and called 911. Paramedics had to revive him with Narcan and rushed to.

him to the hospital. I got a panicked call for my mom in the middle of the night and rushed to the hospital. My parents were already there, distraught. Tyler was conscious but groggy in a hospital bed, hooked up to IVs and monitors. He was extremely lucky to be alive. Seeing him like that, pale, weak, and so close to death, filled me more with sadness and relief than anger. We didn't talk much that night beyond telling him we loved him and were glad he was was okay. The hospital kept him a couple days and the substance abuse intervention team had a blunt talk with him. Next time, he might not be so lucky. They urged him to go from the hospital straight into treatment. Because of the overdose and his legal situation, the state arranged to

put him on a short and voluntary detox hold, with plans to transfer him to a state-funded rehab as part of his court requirements. Basically, they didn't discharge him home, he's being placed into treatment by default. At the hospital, I let the professionals take over. I made it clear in front of him that I would not be paying for or arranging anything this time. So now, Tyler is in a state facility for detox and will be transferred to a court-mandated rehab. It's out of our hands and, honestly, I'm grateful. Perhaps having the system and not the family, enforce the consequences will make a difference. At the very least, we are no longer the ones trying to drag him to get help. Circumstances have forced his hand. I now realize that by constantly rescuing him, we were just delaying the

inevitable. We never let him hit rock bottom, we shielded him from everything. This overdose might have finally been his true rock bottom. It's awful that it came to this, but I see now that nothing I did could have prevented it as long as he wasn't truly ready. He will only get clean when he commits to it, not for us or because we paid for rehab, but because he wants to live. I've made peace with the fact that I did everything I reasonably could, and I don't blame myself for what happened, in the past, I probably would have. He got a second chance at life that many don't get. Maybe this scare will finally push him to embrace recovery, I truly hope it does. But I will not be actively involved beyond offering emotional support. My boundary is for

firm, no financial help, no enabling. If he asks for anything other than a listening year, the answer will be no. This is my final update, as the situation is now truly in Tyler's hands.