Parshas Vayigash - Selling Binyamin as a slave
The Medrash Rabbah says (Bereishis 96:6) אמר רבי סימון בנימוסות שלנו כתיב (שמות כ"ב) ואם אין לו ונמכר בגניבתו וזה יש לו לשלם Rabbi Simon says, “[Yehudah said to Yosef,] in our law it is written, ‘If he does not have the money needed to pay back that which he stole, then he will be sold as a slave (and the money from the sale will be used to pay back the person from whom he stole). However, Binyamin does have money to pay [so he does not need to be sold as a slave.]’” The gemara says in Kiddushin (18a) והתניא (שמות כ"ב, ב') בגניבתו בולא בכפילו “A ganav may only be sold to pay back the principal amount which he stole, but not to pay back the double payment which he must pay as a fine.” Since Yosef had already retrieved the chalice which Binyamin had supposedly stolen from him, the only sum which Binyamin could have been left indebted to Yosef for would have been the double payment which he had to pay as a fine for stealing the chalice. Why then did...