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Case: Along with his older daughter’s ketuba, Reuven wrote a standardshtar chatzi zachar (an obligation to a daughter, which creates the effect of the granting of a present in a will) for 1,000 gold coins. After Reuven’s second daughter got more money in that form than her sister, he wrote another document to his older daughter, for 2,000 coins, to appease her. After Reuven died, his daughter demanded 3,000 coins from her brothers. They responded that the second document was to replace the first one, not to be added to it.
Ruling: The gemara (Ketubot 44a) says that when Shimon gives Levi two documents of a present or a sale, one after the other, we assume that the second one replaces the first. However, the Rif and Rosh say that in the cases of two loan documents between Shimon and Levi, we assume that each one is independently valid. The gemara in Bava Batra (172a) seems to confirm the understanding of two loan documents being complementary. On the other hand, the gemara (Ketubot 43b) says that if there are two ketubot and the second one does not say that it is coming in addition to the first one, we assume that it is a replacement. Nevertheless, the accepted opinion is that regarding loans, one does add onto the other.
P'ninat Mishpat (832)
Various Rabbis
333 - Adding Relatives to Recipients of Posthumous Tzedaka Fund
334 - Adding on to Old Present or Setting New One?
335 - Returning Ribbit With Devalued Currency
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The gemara (Ketubot 44a) says that there are two ways to view the second document undoing the first: admission that the first is false; relinquishing rights (mechila) included in the first. However, we rule thatmechila cannot undo an obligation found in a document, leaving only the possibility of admission of falsehood of the first document. However, such an admission is an unusual course of events, which makes sense only when there is something suspicious about the existence of two documents.
In any case, there is no particular reason to say that the second shtar chatzi zachar, which works like an obligation, should indicate an undoing of the first. Thus, according to strict law, the daughter should receive 3,000 gold coins. However, due to certain local reasons to question whether the father intended to give her so much, it is proper for the sides to compromise.

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