Need to know if you would say something or MYOB since its not your money.
Bill asks Bob to borrow a significant amount of money (5 figures). Bill's situation is completely screwed up and he only tells Bob partial truths or omits major details about why he needs the money. You know the major details and also why only part of the truth is given. Bob mentions to you that Bill asked to borrow money and is preparing to give it to him but expresses concern that he needs it back. From what you know, the chance of Bob getting the money back is very slim. Would you tell Bob the details, tell him to ask Bill about X or would you just MYOB.
Oh, I would mind my own business here. I'm not sure my rationale, but I try not to meddle in my siblings' relationships with my parents (and vice-versa).
I'd simply say "Only give him the money if you can really afford to give it. Chances are you aren't going to get it back" - because this is the truth regardless of the actual people! If asked "why do yo usay that?", I'd just say "it's just the truth of lendin gmoney. You have to "lend" it w/ the expectation that you'll never get it back. If you can't afford that, then don't lend it.".
I would like to say I'd mind my own business, because I don't like to get involved in siblings relationships with my parents. However, knowing that my dad would need the money back, and knowing that he probably wouldn't get it back, I would probably caution him that I don't think that my brother would ever be in the financial place to pay it back.
Normally I would say absolutely but if it's a dad and brother then I'd be tempted to MYOB so as to not cause a nuclear family fight. Could you "strongly encourage" your dad to investigate further and be clear w/ your brother about when he needs the money back etc. and then also "strongly suggest" to your brother that he not borrow the money from dad since dad needs it?
I change my answer. If this was my family I would probably go to my brother and say "hey, I know you are full of shit and dad can't afford this loan, so back off and go elsewhere or I'm going to tell him what's up".
I would call Bill and tell him you know he is taking advantage of Bob/Dad and tell him he needs to figure out some way to get the $ he needs and leave dad out of it or I will tell dad/Bob the truth.
I change my answer. If this was my family I would probably go to my brother and say "hey, I know you are full of shit and dad can't afford this loan, so back off and go elsewhere or I'm going to tell him what's up".
The only person I ever see in my life asking for a large sum of money is my sister. Even in dire circumstances I would be hesitant. She has borrowed money from my parents and her ILs multiple times.
With my parents, she makes one payment/installment, and then never pays them back.
I just don't stomach that. Even $5 a week is progress. But ignoring that you owe people money? Wrong.
Seeing this trend makes me not want to even gift her money if she were in need.
I would combine answers, I'd tell dad it's a lot of money, but even if it were $1000 you should never loan money you will need. Just in case it's not paid back by the time you need it.
And I'd tell brother to cut it out and solve his own problems without involving our father who is close to (or already) retirment and will need that money to live.
I would probably go to my brother and say "hey, I know you are full of shit and dad can't afford this loan, so back off and go elsewhere or I'm going to tell him what's up".
I think you can either do this or tell your dad without involving your brother, depending on which you're more comfortable with and which better suits your family dynamic.
Factors that might be worth considering: Would you want your dad to keep your conversation confidential? If so, do you trust him to do so? Could speaking up damage to your relationship with your brother? Do you care if it does? You might not, I'm just trying to think of potential issues that might help steer you in one direction over another.
IMO the only crappy way to go here would be to say nothing. Letting your dad potentially lose a 5-figure sum when you could have prevented it is unthinkably shitty. I majorly side-eye the people who told you not to say anything.
There isn't much of a relationship with Bill, due to the details of the situation going on. Bob thinks the sun rises and sets on Bill and believes he's just had some unfortunate circumstances. I'm trying to decide if causing WW3 by showing Bill for the person he is would be worth it.
I would think it would be worth keeping your dad from losing tens of thousands of dollars. But yeah, I don't blame you for kind of not wanting to deal with the fallout.