Choosing safety over freedom
Parshas Mishpatim is loaded with laws. Among them is that of the Jew who has hit rock bottom. Either he has been reduced to stealing and has no money to pay it back or he proactively sells himself because he has no prospects at all.
Even though the individual was brought as low as one can go, he must be treated with some respect.
His master is not allowed to give him pointless work or put him in a situation of anxiety like saying to continue working at something until his return with no clearly set time. The master also must be sure that the slave's standard of living is on par with his own. Should he have only one pillow, he cannot keep it for himself and leave his slave without.
So the situation for the slave is not so bad. All his basic necessities must be met by his master who must even provide for the slave's wife and children. One can see the attraction this can have for someone who had been brought to desperate straits when on his own.
Nevertheless, the Torah does not want one to remain a slave but to live as a free man who recognizes only the Master in Heaven. This is why we have a halacha that is strikingly at odds with the general rule of avoiding any marks on one's body. The slave who decides that he doesn't wish to go free at the end of the contract period is allowed to stay through the yovel year, but he first must have his ear pierced at the doorpost.
This alludes to the doorpost of yetzias Mitzrayim when the Jews were taken out of slavery to become a free people. This individual is throwing away that lesson that he heard, and he is considered far more culpable for that than for having committed the sin of stealing.
The slave has no individual responsibility; it is the master who must make sure he is clothed, fed, sheltered, kept healthy, etc. That is very appealing for some people, to play it safe, follow the orders of the wise master, and not have to make any decisions for oneself. But that is not what the Torah wants of us. The ideal is not the safety of slavery but the freedom of choosing for oneself to do what is right.
Torah is, after all, synonymous with freedom. We're told to not read charut as engraved but cheirut as in freedom as the key quality of the luchos that symbolize Torah life.
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