I can't say a straight yes or no. Do what your conscience dictates. You justify your decision by predicting whether you feel good about it (because you helped your brother and his family) or you feel bad about it (because you jeopardize your own future and the lot of your potential offspring in life.)

If you think it's greed that stopping you from giving him more money, well, you have to look at this way: is the money you give him going to create an essential shortcoming for you? Or does the loaned amount amount to nothing more than a drop of water in an endless sea, so to speak.

You also have to consider whether your other siblings helped him out. You don't have to be the sole bearer of this burden, if I may call it that.

You also have to consider that people, even siblings, have completely different temperaments. If you give, your other siblings may not take your gesture as an example to follow.

Lend him the money and write up a contract of payment where he is legally bound to repay you.

It makes no difference where the money came from, he had his part and screwed it up, unless your part was much bigger than his why should you feel bad about his screw ups?

Family can sometimes be your worst enemy.

The key question you should ask yourself is this: Is your money actually going to help him?

If the money isn't helping him and he keeps getting himself into financial trouble, he doesn't need more money, but good advice. Perhaps you could set him up for financial counseling?

I think you're doing the right thing by helping your brother and it's in both of your best interests to ensure that the help you're giving him is amounting to something and not ending up down the drain.

And what will he do when the brother doesn't pay him back? Sue him? You're giving the sort of advice that destroys families.

It is unfortunate that your brother's business did not work out well. Loaning someone (total stranger or your beloved brother) money to save a failing business is a poor use of your assets. It's a poor use of anyone's assets to prop up a business that is going broke--as many of them do. Give him enough of your money to keep the shop afloat and you may both end up without the cash you started out with.

Your brother and his family are not going to die of starvation if you make no further loans. I suppose your brother and his wife are sufficiently resourceful people who will find ways to put food on the table, pay their mortgage, and so forth. Your brother's business venture belongs to him and his wife -- not you. It's his gamble, not yours. Sometimes gamblers lose. Sad, but that's the way things worked out.

You have already helped your brother. You didn't deny his request for assistance. Just because you helped him in the past doesn't mean that you should continue. He hasn't been able to make repayment so far, and that will probably continue.

Chances are you and your siblings will not receive another large inheritance. You have needs too: college costs money. It would be helpful for you to finish college without debt -- and with some assets in place.

Question: under what terms did you loan your brother money? Was it more like a gift masquerading as a loan? Was there a contract written up and signed committing him to repay you? Was all this a verbal understanding?

Polonius says to his son Laertes, before the boy takes off for Paris (this is in Hamlet):

Neither a borrower nor a lender be;
For loan oft loses both itself and friend.

Do loan him the money, but most importantly don't reduce contact merely to loans, rather keep in touch until you're sure he's stable. If you intend on financially supporting him for a while, do it on a budget, so that he doesn't grow complacent.
From the description offered, that seems to be the main issue; you've become his reserve and he's growing increasingly complacent.

Teach him to fish, rather than giving him a fish everytime he's hungry, as independence is the best gift you could offer.

This is a bit of a minority report it seems, but loans are a matter of business. Is this a good investment? Is the return potential proportionate to the risk? the answer is obviously 'no', because otherwise the bank would lend.

If your brother is in trouble and needs money, give him whatever you can. He obviously cannot afford your loans.

The problem is that if you give him every time he asks, he will start thinking (more or less subconsciously) that whenever he fucks up financially you'll be there to save him, and so he will likely be more careless with the money than if he had worked hard for it. You have to make him understand that it is problematic both for you and for him, that he cannot always rely on you to give him money to get him out of a difficult situation.

That being said, if what he asks for is a small percentage of what you have, and if it wouldn't make a huge difference for you but it would make a huge difference for him, and if you trust that he's not going to gamble that money away and ask you again soon, then if I was in your position I would help him, after making him understand that you have to plan for your future too and you can't keep giving him again and again.

Keep also in mind that investments are risky. What if you don't give him the money and your investments crash and you end up losing more than the amount he was asking for? Either the investment is really safe but then you wouldn't earn much from it so it wouldn't change much to lend him the money if you trust that he'll pay you back, or the investment is risky but then you might very well lose. If you believe that your investments are really safe and that you will earn a lot from them, consider that you might be wrong (for instance if you invested in cryptocurrencies that's really risky).

Wow, thank you so much for your thoughtful responses. A few things jump out at me:

First I'd like to respond to BitterCrank since you asked a direct question. The loan was never intended to be a gift, and it was always clear that he would (supposedly) repay me.

1. As far as "investments", I'm about 50% sure I'm never getting this money back. I'm not trying to help him keep his business afloat (he has already resolved to close shop, but he still needs to pay rent for the remainder of his lease). But this would be more of an investment in my relationship with him. That being said, I don't want to be taken advantage of just because I love my brother.

2. I honestly don't want to give him advice. This is for a couple reasons. First, I don't know a single thing about financial planning. I just happen to live frugally and it has worked out for me. On top of that, he has what I would like to call "big brother syndrome". He likes to give me advice (ironic), but he's not so big on the listening.

My other siblings have not helped at all and there is a bit of sourness between them. In fact there is a big rift in my family now due to "who got what" when my grandfather passed away. I don't want that to spread to me and my brother too.

The heart of my conflict is this:
-Don't loan him money: risk him being (unjustly?) angry with me.
-Do loan him money: probably never get it back and feel a bit taken advantage of.

Thanks again, I really appreciate you guys helping me think this through.

I think logic suggests that you should stop lending him money. Two reasons:

1. Giving him money has not seemed to help him in the past and seems unlikely to help him in the future.

2. It's starting to negatively affect you.

Of course, decisions with family are hard to make based on logic alone. How willing you are to hurt yourself to maintain a cordial relationship with him is up to you.

But then you also have to ask yourself, will you sour toward him if he keeps it up? Will he sour toward you if you don't comply? Do you want to be in a relationship that depends on money?

-Don't loan him money: risk him being (unjustly?) angry with me. — Stanley

Do you have reason to fear his affection will be withheld if you say no? If you do, you're being manipulated.

He likes to give me advice (ironic), but he's not so big on the listening — Stanley

Not ironic. Controlling.

In fact there is a big rift in my family now due to "who got what" when my grandfather passed away. I don't want that to spread to me and my brother too. — Stanley

Was all well among the siblings prior to this inheritance, or have there been issues of distrust prior to this? This sounds more complex than you're presenting. If your brother were a stand up guy, the sort who'd help you out through thick and thin, and who now is in need, why wouldn't your other siblings help him now in his time of need? Probably because he's not all these things? Am I right or wrong here?

The key question you should ask yourself is this: Is your money actually going to help him? — Tzeentch

Tzeentch is right. The question is whether the money will actually be useful for him. If he’s a spendthrift who’s likely to squander it, there is no such thing as a brotherly duty on your part to help him ruin himself.

On the other hand, there is no duty to stick to strict economic principles. You are not a bank and business principles are not your ethical guide.

When inheritance is distributed the heirs commonly get an equal share. The reason for that is simplification and convenience. But since none of the heirs had really deserved anything in the first place, it’s not really a matter of justice. When real justice prevails the person with the greatest need gets the greatest share. Maybe your grandfather would have wanted to give more to your brother since he was most in need?

But again, it’s a matter of real need. If he’s likely to waste the money, he doesn’t need it.

Too often when we try to solve ethical dilemmas, we fall into the trap of thinking in formal principles. We imagine ourselves to be a financial institution, a government, a court of law or a computer. We are not. We are human beings making human decisions and therefore we must treat every case as something unique and individual.

The question to ask is always: How can we, in this particular case, be likely to reach the most beneficial outcome for everybody?

Tzeentch is right. The question is whether the money will actually be useful for him. If he’s a spendthrift who’s likely to squander it, there is no such thing as a brotherly duty on your part to help him ruin himself. — Congau

Totally disagree actually. These are siblings, with relationships going back to their earliest memories, dealing with parental relationships, grandparents, their spouses, and on and on. It's not isolated to whether this will help the brother by his his own narrative, as he talks about soreness among the other siblings, envy over the inheritance distribution, and his brother's not respecting his opinion.

It's Stanley's money. All his. No one has any moral or legal right to it but Stanley, which ought to be accepted by brother. So, Stanley ought to do what is best for Stanley, which might be to stand up to brother. Might not be too, but that's the question, not what is best for brother.

First of all, money from family is never a loan in the financial sense, despite what the giver may think or have been led to believe. A loan is a relationship built purely on the exchange of money. Your relationship already exists, and so is not contingent upon any exchange of money. At best, this ‘loan’ is for life, just as your relationship is. Your suspicions are correct here. Any money he returns to you before your relationship ends will be considered by your brother as over and above his obligations to you.

From what little you’ve told us, it does seem as if your older brother is playing on his position in the family (ie. the respect he assumes as ‘older’ brother) to acquire more than his initial share, rather than acknowledging the humility of his financial position or the generosity you display in helping him when your other siblings refused.

You say that you see this money as an investment in your relationship with him - be careful of this thought. If you’re expecting your further generosity to inspire gratitude or respect from him, then I would say that you are being taken advantage of. If you’re trying to avoid his anger, then that’s not a good reason to give him the money, either. That’s fear - and you should have no reason to be afraid of your brother’s anger, or of him withdrawing his love for you over money. If he chooses to stake his relationship with you on money, that’s his problem, not yours. Don’t you make the same mistake.

If you say no to giving him money, it will not change your relationship as brothers, despite what he would have you believe. Your love for him has never been measured in dollars and neither has the love of your other siblings. Remember that and remind him of that, too.

But if you’re willing to give him the money, knowing that it won’t come back and won’t change his attitude towards you one iota, and may even increase the chance of him asking for more, then that’s different. Only you can make that call.

A family relationship is with you for life. Money is either nothing between family, or it’s everything. It seems that you brother is making it everything...

Do you have a reasonable expectation that he will repay the "loans"? It may be his sincere intent but how will he be able to do so? If his business is failing then what will be the future source of income that will enable him to repay them?

If, however, you give him the money because you believe it will help him and would do so even if he can never repay you then you need to evaluate whether and to what extent this will actually help him. Will it make him solvent or enable him to live without further loans from you? You said you have already given him several loans. Do you expect that for some reason this will be the last one? Were all the others for this failed business? What will he do once the business closes?

this would be more of an investment in my relationship with him — Stanley

You might get paid back. Time will tell. In the meantime...

Don't mix business with familial love. Loans are loans, love is love. Don't confuse the two.

The investment that matters is the relationship that has been created and built up over time and with common experiences between you and your brother: you grew up together in the same home. You (plural) have invested decades of time together in each other. You are invested. You don't need to invest cash in your brother's failed business venture to bolster your relationship.

Business dealings between family members and friends can (and fairly often do) turn bitter. It can be hard to separate out loans and love.

There is a small moral hazard here. A moral hazard exists when loans enable people to take risks without having to shoulder the consequences. Loaning businesses money sometimes creates major moral hazards -- sometimes really really big ones, like when the government bailed out AIG in 2008 to the tune of $67,835,000,000. There was moral hazard up to Wall Street's eyeballs that year.

It's Stanley's money. All his. No one has any moral or legal right to it but Stanley — Hanover

Legally it is Stanley’s money. No one has the legal right to it but him. From a legal standpoint the case is very simple and clear-cut. But that was not the question here. From the fact that something is legally unambiguous, we can make no moral conclusion. What does it mean to have a moral right to something?

Let’s change the premises of the story a little and see what happens. Let’s say Stanley’s brother was seriously ill and needed the money for medical treatment or else he would die? Does Stanley still have the moral right to the money? The legal issue is still as unambiguous. Legally the money still belongs to Stanley only. It’s all his and no judge could force him to pay for his brother’s hospitalization. But morally? I hope most people would agree that Stanley would be doing something extremely bad if he didn’t save his brother’s life.

So what has changed in this revised example? Only that the brother’s need has become much greater. Now we could debate how great his needs should be for him to have a moral right to the money, but then we admit it’s not a matter of principle anymore but of degree. Moral rights cannot be determined by simple formal facts the way we decide on legal rights.

From a legal standpoint the case is very simple and clear-cut — Congau

I said:

No one has any moral or legal right to it but Stanley — Hanover

Let’s say Stanley’s brother was seriously ill — Congau

He's not though. Stanley said he made bad investments, he doesn't respect Stanley, and he withholds affection if Stanley doesn't do what he asks.

That's why I said the money is Stanley's, morally and legally. We could change the facts and make the money legally his brother's also, but again we'd be answering a different question.

And what will he do when the brother doesn't pay him back? Sue him? — Tzeentch

Apparently the brother has no idea what a loan is, as he has already failed to pay back several. Asking him to sign a contract would force him to see the legal side of money lending. He has the choice of not signing it and looking else where for a loan.
If he accepts and fails to make good the payment, at least he will think twice about asking for more money.
You yourself said that he needed an education in finances. Asking for a contract would be a good place to start his learning.

You're giving the sort of advice that destroys families. — Tzeentch

"A friend in need is a friend in deed." Applies to family members as well.

I don't know much about the family being talked about here, but I can name several families that have been badly messed up because of money problems like this.
I would rather have a family member refuse to talk to me because I would not give him money than to not want to talk to him because of his bad actions. If he does not want to talk to me that is his problem not mine, my door would always be open for him.

Getting the legal system involved is a terrible idea if one values their familial ties, which the OP clearly does.

Simply not lending any more money, and thinking about some other way to alleviate the brother's troubles, would be infinitely better.

Give him the money, if you can.

Stanley said he made bad investments, he doesn't respect Stanley, and he withholds affection if Stanley doesn't do what he asks.
That's why I said the money is Stanley's, morally and legally. — Hanover

Could you please clarify. Do you agree that a moral and a legal right are two different things? Someone can have the moral right to something but not the legal and vice versa. Right?

In this case there’s no debate about the legal issue, the money legally belongs to Stanley, but I don’t understand how you can state in such a matter of fact way that “It's Stanley's money. All his. No one has any moral (..) right to it but Stanley.” You may be right in the end, but for such an absolute statement we would need to take a whole range of issues into consideration. The facts that are already given may suffice to give Stanley a clear advice, but that’s not the same as saying that he has an unambiguous moral right to the money.

I also have some money. It’s legally mine, no doubt about that. But in this world, how can I make an absolute moral claim to it. There are people starving, but I just bought a new iphone etc. I may not have done something terrible and certainly nothing different from most people around me, but I can’t say that I’m a hundred percent on moral safe ground. I don’t want to state in absolute terms that I have a moral right to my money since I partly got it through circumstances that were not in my control – like being born in a rich part of the world.

Now Stanley got his money through even less controllable circumstances, and he has a brother close by, so we don’t have to remind him of starving children in Africa. Maybe I would also advise him to keep his money, but I certainly wouldn’t say absolutely that he has a moral right to it. Few of us have.

In this case there’s no debate about the legal issue, the money legally belongs to Stanley, but I don’t understand how you can state in such a matter of fact way that “It's Stanley's money. All his. No one has any moral (..) right to it but Stanley.” You may be right in the end, but for such an absolute statement we would need to take a whole range of issues into consideration. The facts that are already given may suffice to give Stanley a clear advice, but that’s not the same as saying that he has an unambiguous moral right to the money. — Congau

I agree we could concoct a situation where Stanley has no moral right to the money and that he ought give it to his brother. My point is that there is nothing in the actual post of Stanley suggesting the brother has some moral right to it. Sure, if brother is dying, Stanley owes him some money, brother has been there for Stanley in the past, etc might sway me to say Stanley should give some to brother. What I've read about brother doesn't reveal any redeeming quality morally entitling him to the money.

I'm glad I posted here, reading your responses has helped me develop my view on a few of things:

1. Although the money is inherited it was still worked hard for. I am to use it as responsibly as if I had earned it myself. Someone else did indeed work hard for it and then trusted me to use it responsibly. Of course helping those I love could be considered responsible usage, which leads me to...

2. Is brother in need? I don't know this for sure. I'm not sure how much of his inheritance he has spent - however there are several annual distributions (from a trust) which he will receive for the rest of his life. I believe he can make it work, and this loan is just to keep him a little more comfy. I am speculating a little bit here but I think he has a parachute if he really (really) needs it. After reading your responses and thinking it over I'm more inclined to let him get uncomfortable, but I'm ready to help him when he is in "actual" need (not sure what that would look like at the moment - but fairly certain it's not now.).

3. What is most beneficial for everyone? Even if I were thinking what is most beneficial for myself only that would include my brother being happy and financially stable. This loan would be more of temporary pain relief. He still needs to find a way to make a living and of course a loan does in no way accomplish that.

I have't taken my other siblings into consideration at all because what they do with their own money is their business. They may be making a better decision than I am by not loaning him a dime, maybe I'm just acting as the enabler.

Sorry I keep dropping new info about the situation with my posts. It's a complicated situation as you can imagine and also very personal.

So, I'm leaning towards declining to help him now (This discussion has changed my mind!). Open to hear more thoughts, so far your responses have been very helpful to me!

Just got off phone with brother. It was surprisingly painless and he even thanked me for helping in the past. He also said my dad might help him out. Thanks again for your advice all, it was truly helpful.

Good. It seems like you agree with me that legal rights and moral rights are different. I’m sorry for harping on this since it’s no longer a matter of what advice to give Stanley in this concrete case – I’m also inclined to advise him to withhold the money. However, I still react to the language you are using when you call it a “moral right”. Please forgive me if you think it is irrelevant, but I think it is important.

I think Stanley has grasped something essential when recognizing that it is a dilemma and racking his brain over what to do. His brothers may have been quick to play the “moral right” card and thereby removing all doubt from their mind. It’s a common device for the ethically lazy to arrogantly state that they have a right and in this way escape from tiresome pondering.

I’d prefer that we never used the expression “a moral right”, at least not for specific situations. A right is inherently a legal term and denotes benefits that the law happens to grant us. It only considers what the law has already defined as relevant and therefore it’s possible to reach a final conclusion. But what moral law or laws do you invoke in this case? There aren’t any. The best we can do, and that’s exactly what you are doing, is to weigh the circumstances and use the limited information we have, to reach a sufficiently accurate conclusion, not an absolute one. There will always be doubt because there are no absolute moral rights.