I do not profess to understand or know all the circumstances. If the small guy lived beyond his means and had to "keep up" with others, there is less sympathy I have. If living beyond his means was part of the problem, then it would seem to me he placed more value on living high on the hog, over the friendship. We face this sort of problem within my wife's family. One sibling and his wife live way beyond their means. Tapped into her mother's finances and she cut them off. Now they want to tap into my father in law's finances/get their share of the inheritance now, and it seems they will want their share and then some AFTER. They actually told my father in law they were looking to their inheritance from his estate as their only retirement fund. Anyway, to get back on track. If the small guy didn't live beyond his means, then the friendship remains an important part of this.
I agree the money lent may end up "being a gift" since there is little to nothing to recoup these losses. Going to court is a last resort. The only ones who will be satisfied will be the attorneys, because they will be greatly compensated. Saw that with two brothers who were fighting over how to divide up a jointly owned possession. It took something like 17 years and a lot of money paid to their respective attorneys. They had the division about 95 percent done, but one brother wouldn't press the other brother hard enough to take care of his final responsibility. Cost even more once the statute of limitations had run out and essentially had to start over.
If the three of you cannot or do not know how to resolve this issue, perhaps a mediator might be a good first step. Nothing is binding under mediation, unless some legal documents are drawn up whereby all parties must fulfill their respective responsibilities. This allows a low pressure exchange between the involved parties, accompanied by some neutral "third party" who may be able to structure or channel the dialogue. Again, this allows the parties to work things out themselves with an impartial third party mediator who can facilitate.
If this is unsuccessful, then one could go to binding arbitration. This is more involved and a neutral third party judge will hear both parties issues to be resolved and make a decision, which is legally binding. I cannot recall if attorneys are or are not involved in this process, but if so, the attorneys are needed to a lesser degree versus going to court and getting into a legal battle.
As a last resort, the parties can go to court and fight it out there with their hired gun attorneys. In suspect, that you as the "third wheel" are probably going to get drawn into this quagmire and have to offer testimony, and perhaps taking a side with one or the other, not something I would enjoy. One of the other two might be your friend in the end, and the other not so much your friend.
This will certainly test the friendship. If there is nothing there with the "small guy," remember that you cannot squeeze blood from a turnip. If nothing is there of value, there is nothing to recoup these losses.
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