Kiddushin 20 continues a discussion of the redemption of Jewish slaves and ways in which the redemption process can be accomplished or even expedited. As part of this discussion the gemara presents a progression of unfortunate events which can lead to a man selling himself into slavery. Repeated elsewhere in shas (Sukkah 40b and Erchin 30b as indicated in the Mesoras Hashas), the statement of R' Yosi B'R' Chanina is quite fascinating.
The gemara explains that the inital downfall begins when a person makes business transaction concerning shmittah produce. If a person violates the rule and sells the produce (rather than making the permitted use of eating it), eventually he will wind up in debt and will need to sell his personal property. If he does not recognize the error of his ways, this will not be sufficient and he will then need to sell his fields, followed by his home. The next item he will sacrifice is his daughter who he will sell as an amah ivri'ah. This of course will not be enough and he will wind up borrowing money on interest and then ultimately he will sell himself into slavery to pay the debts.
On Gittin 20b, R' Huna B'R' Hinna asks whether a Jewish slave can be redeemed through partial payment. As part of his question, R' Huna asks whether the answer can be derived through a gezera shava comparing this redemption with the law of redemption of ancestral fields. He then completes his question by theorizing whether the gezera shava can only be applied leniently (to allow a partial buyout of the slave) but not when it would result in a hardship.
Tosafos (d'h Geulaso) comments in the name of Rabbenu Tam that this would not be a complete gezera shava because we don't pick our spots in applying a gezera shava. It either applies l'kula and l'chumra or not at all. Tosafos indicates that the limud would really be just a gilui miltsa b'alma.
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