And if the slave (who worked for his master six years and is about to go free) says, “I love my master, my wife, and my children. I will not go free. His master shall bring him to the judges, and he shall bring him to the door or to the doorpost, and his master shall pierce his ear with an awl, and he shall serve him forever.”
On this possuk Rashi explains, "...Why was the ear specifically chosen to be pierced instead of another organ? Rabban Yochanan ben Zakkai said: The ear that heard on Har Sinai, “You shall not steal” (Shemos 20/3) and stole, shall be pierced...".
In other words, this possuk is speaking about someone who stole, and when he was caught, he did not have the money to pay back the one from whom he stole. Bais Din therefore sells the thief as a slave and the money they receive goes to the one from whom he stole. Rashi explains the reason for this is in order to remind the thief that the reason he became a slave was that he transgressed the aveirah of, "lo sig'nof" -You shall not steal- that he heard with his ears at Har Sinai.
Zera Shimshon asks; according to this, why is his ear pierced only after working for six years and after he chooses to remain a slave? It would seem that he deserves this punishment right at the time that he was caught stealing which is the time that he transgressed what he heard on Har Sinai, "low sig'nof"!
Zera Shimshon answers in light of the Nemukai Yosef's commentary (Moed Kattan (17a)) that although thievery is ALWAYS prohibited no matter the thief's intentions and his situation and he must return anything stolen, there is a difference if the thief had good intentions or bad ones. If the thief knew he was doing something wrong but refuses to return the stolen money or object, Bais Din can put the thief into chayrem (excommunication). However, if there is a possibility that he did not have any corrupt intents then Bais Din cannot put him into chayrem.
Zera Shimshon explains that in the same vein the Torah commanded to pierce the slave's ear only after they establish "beyond a shadow of a doubt" that this man stole with purely bad intent. This is only after he had the chance to go free but chose to remain a slave, and not right at the time when he stole.
How is this?
An impoverished man who does not have enough money to support himself and had large debts has two choices in front of him. One choice is to sell himself as a slave and with the money he receives he will repay his creditors. The other choice is to steal with the intent that when he earns money, he will pay back the one from whom he stole.
It is written in Gemara (Babba Basra 116a), "R' Pinchus bar Chama taught, 'Poverty in a person's house is more difficult than fifty plagues...'".
Maharsha learns from the fact that R' Pinchus bar Chama said "Poverty IN A PERSON'S HOUSE..." and not simply "Poverty" that even when others around him give him the money that he needs, his situation is still worse than fifty plagues since there is still poverty IN HIS HOUSE. He has money to pay for what he needs but "the house" is still poor. The reason for this is that he is still not independent and he must depend on others for his livelihood.
According to this, the thief in the above possuk made his decision to steal with the following logic. If he sold himself, he would not alleviate the pain of poverty, like the Maharsha explained, because he is now being supported by his master. In addition to this, Chazal (Kidushin 22b) learn from the possuk, "they (Bnei Yisroel) are my slaves" that one should not sell oneself to be a slave to someone else since we are already Hashem's slaves. He therefore chose to steal with the intention to pay back so the money that he earns will be his and therefore he will alleviate the poverty in his house and he wouldn't be a servant to a master.
You might ask, "What did he gain?", to steal with the intent to pay back is also assur?
He reasoned that this was still a better option. Firstly, the prohibition to sell oneself is written clearly and openly in Chumash, "they are My slaves", while the prohibition to steal with the intention to pay back was only alluded to from the fact that seemingly the Torah wrote extra pessukim. Secondly, stealing with the intent to return is not looked upon as something wrong. (The Gemara in Babba Kama writes that this Halacha wasn't even clear to Dovid HaMelech!)
Therefore, at the time that he stole, Bais Din judged him favorably that he was just making the best of a bad situation and therefore he doesn't deserve to have his ears pierced.
However, at the end of six years when he had a choice to go free but chose to stay on as a slave, Bais Din saw that he does not really mind being dependent on others and he also doesn't mind staying a slave and transgressing the issur of "they are My slaves".
Since the two arguments that were used to judge him favorably were proven false Beis Din can now establish with certainty that he had ill intentions when he stole and deserves to be punished by piercing his ear!
To summarize, Rashi explains the reason that a slave who chooses to continue to be a slave even after he had the opportunity to go free after six years has his ear pierced is because his ear heard on Har Sinai that one should not steal and even so he stole.
Zera Shimshon asks that if this is the reason, why didn't the Torah command his ear to be pierced right when he was caught stolen and not only after he worked for six years?
Zera Shimshon answers that this possuk is speaking of someone who had debts and he so no way how to get the money to pay his creditors. Even though one may never steal, even when a person is in very dire straits, the Torah gave the punishment of having an ear pierced only to someone who had no good reason to steal. Therefore, it is only after he had the opportunity to go free and opted to stay a slave can we negate any good intentions in his stealing.
