Arachin 30 - Redemption of Ancestral Fields

If the hereditary owner of an ancestral fields sold it to the first buyer for a hundred coins (zuz), and the first buyer then sold it to the second for two hundred coins, then when the original owner comes to redeem the field, he calculates the redemption fee only according to the hundred coins he paid the first buyer, since the Torah said, " And he shall calculate the years of his sale and return the remainder to the man to whom he sold it ."

On the other hand, if the owner sold the field to the first buyer for two hundred coins, and the first buyer then resold the field to a second buyer for a hundred coins, the owner redeems it based on the price of the second buyer, that is, one hundred coins, since the Torah said, " He shall calculate and return the remainder to the man ..." - which man? - the one who currently owns the field.

How can the same phrase be interpreted in two different ways, both times to the advantage of the owner? Abaye said, "I am today as sharp as Ben Azzai, who was smarter than all the Sages, and I will explain: fields are compared to a Hebrew slave, and Hebrew slave was given multiple leniencies by God."

Art: John Singer Sargent - Home Fields