Introduction This mishnah teaches what type of land must be used in order to repay debts. Its connection to “tikkun olam” is that the sages shaped some of these laws using “tikkun olam” type criteria. That is to say they tried to take into social needs when making these rules.
Damages are paid out of [property of] the best quality; The rule that damage payments are made out of the best of one’s land is seemingly stated in Exodus 22:4, “When a man lets his livestock loose to graze in another’s land, and so allows a field or vineyard to be grazed bare, he must repay the best of his field and the best of his vineyard.” However, there is a debate over this issue. Rabbi Akiva interpreted this to mean that the damager must pay back from the best of his (the damager’s) land and Rabbi Ishmael interpreted it to mean that the damager must pay back with land equivalent to the best of the other person’s land. If this mishnah goes according to Rabbi Ishmael than the “tikkun olam” is that although the Torah does not demand that the damager pay back from the best of his own land, the rabbis demanded that he do so in order to deter people from being negligent and causing damage. If the mishnah goes according to Rabbi Akiva, then the Torah itself ruled because of tikkun olam. Although tikkun olam usually implies a rabbinic enactment, this is not always the case.
A creditor pays out of land of medium quality, According to the Talmud, Torah law dictates that when a debtor collects land in payment of his debt, he collects from the debtor’s worst property. Seemingly this would be good for debtors, certainly a noble goal. The problem with this is that it might end up deterring lenders and thereby make it difficult for people to get the loans they need (especially if they are farmers.) People will be hesitant to lend money if they know that if the debtor defaults they will collect from lousy land. In order to encourage people to lend money (remember it was without interest, so lending was a form of charity), the rabbis enacted that if a debtor defaults the creditor collects from property of medium quality.
And a ketubah is paid out of land of the poorest quality. Rabbi Meir says that a ketubah is also paid out of medium quality land. There is a debate over what type of land a woman receives upon collecting her ketubah. Collecting a ketubah is like collecting any debt the husband (or his estate) is a debtor to the woman. Therefore Rabbi Meir holds that just as usual debts are collected from middle quality land, so too is the ketubah debt. However, the first opinion in this mishnah holds that normal debts are not totally analogous to ketubot. With regard to a normal debt, the rabbis ruled that it is collected from middle quality land in order to encourage people to loan money. No such encouragement is needed with regard to ketubot, for women will marry whether they will collect their ketubah from middle or poor quality land. Since there is no special reason that the woman should collect her ketubah from middle quality land, she collects from poor quality land, as is the Torah’s rule for all debts.