When someone guarantees the payment of the Ketubah, he incurs no obligation. If the husband later defaults and does not pay the Ketubah to his wife, our guarantor is off the hook. Why is that? The guarantor relies primarily on the husband to pay the Ketubah and reasons that he will most likely never have to pay. Moreover, he is simply doing a mitzvah to encourage the pair to marry! That is why we can assume that he does not seriously obligate himself.
We mentioned earlier that a debt if one cannot pay it, is collected from his lands of medium quality. Why is that? In truth, he could even give his worst land. The Torah said the lender "Cannot come into the house to take a deposit, but must wait outside till the debtor brings him something." What will the debtor bring? – Of course, the worst. However, the Sages raised the borrower's obligations, for otherwise, nobody would want to loan money to his fellow.
However, when a man dies and a creditor comes to collect the debt, he can only collect from the worst. This is so because he collects not from the borrower but from the orphans that are left. If they are minors, they surely need protection, and even if they are adults, they likely have not paid attention to their father's loans and can be easily fooled. Here the Sages left the Torah law intact because lenders seldom consider the possibility of the borrower's death and would give out loans anyway.
Art: La Mariée - The Bride - by Marc Chagall
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