Our Gemara on Amud Aleph discusses a legal principle: anyone who pays as punishment for a transgression is not flogged for that same transgression. In other words, in most situations, a person does not incur multiple penalties for the same infraction.

The Mekhilta (Shemos 21:6) discusses why the Jewish servant who is sold to repay stolen goods, and then chooses to stay in servitude beyond his indenture, must have his ear pierced by the door:

What is the reason that the ear had to be pierced rather than any other limb of the servant’s body? Rabban Yochanan ben Zakkai said: That ear which heard on Mount Sinai, (Shemos 20:13) “Thou shalt not steal,” and yet its owner went and stole and was therefore sold as a slave—let it be pierced! Or, in the case of one who sold himself from destitution, having committed no theft, the reason is: That ear which heard on Mount Sinai what I said, (Vayikra 25:55) “For unto Me the children of Yisroel are servants,” and yet its owner went and procured for himself another master—let it be pierced! 

The Panim Yafos (Mishpatim) asks: since we have a principle that one does not pay and receive corporal punishment, why do we pierce this person’s ear? He already paid his debt to society by working to pay off his theft. Also, if it is a punishment for stealing, why does it only apply when he chooses to stay as a servant past his contract? (Of course, we could give a cold, Litvish answer that the piercing is not a physical punishment but rather a mark of recognition and shame, or a way to make his contract distinct and permanent. However, let us pursue the derash question, as there is a certain justice to the idea of not paying a double penalty, and in spirit, all parts of the Torah should represent a consistent form of justice.)

Panim Yafos brilliantly answers: The slave declares (Shemos 21:5), “I love my master, and my wife and children: I do not wish to go free.” If so, then the prior years of servitude were not a punishment, as this person seems to have enjoyed his stay. We then say retroactively that it was not a financial payment, and therefore he receives the corporal punishment of piercing. 

I will add a related allegorical idea from the verses. The man says he loves to be a slave and does not want to go free? Enslavement to desires is also a form of servitude. Plato’s *Republic* quotes an old sage who remarked that he is “grateful for aging that allows him to escape from the raving and savage slave master of desire.” The verse (Shemos 32:16) describes the Stone Tablets as “Charus - Engraved.” Eiruvin (54a) makes a play on words that they offer “cheirus - freedom.” The person who stole, and thus is a slave to his desires, has not quite gotten the message. He says, “But I love my master”—I love being chained and attached to physical pleasures. This person must get an extra pinch to remind him about his obligations from the covenant at Sinai.   

Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation

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Rabbi Simcha Feuerman, Rabbi Simcha Feuerman, LCSW-R, DHL is a psychotherapist who works with high conflict couples and families. He can be reached via email at simchafeuerman@gmail.com