Exodus 21:2

If thou shalt have bought a son of Israel, on account of his theft, six years he shall serve, and at the incoming of the seventh he shall go out free without price.

IF THOU BUY A HEBREW SERVANT. G-d began the first ordinance with the subject of a Hebrew servant, because the liberation of the servant in the seventh year contains a rememberance of the departure from Egypt which is mentioned in the first commandment, just as He said on it, And thou shalt remember that thou wast a bondman in the land of Egypt, and the Eternal thy G-d redeemed thee; therefore I command thee this thing today. It also contains a remembrance of the creation, just as the Sabbath does, for the seventh year signals to a servant a complete rest from the work of his master, just as the seventh day of the week does. There is in addition a ‘seventh’ amongst the years, which is the jubilee, for seven is the chosen of the days [to be the Sabbath], and of the years [to be the Sabbatical year], and of the [seven] Sabbaticals [to be the jubilee]; and they all point to one subject, namely, the secret of the days of the world — from bereshith (in the beginning) till vayechulu (and they were finished). Therefore this commandment deserved to be mentioned first, because of its extreme importance, alluding as it does to great things in the process of creation. This is why the prophet Jeremiah was very stringent about it and said, Thus saith the Eternal, the G-d of Israel: I made a covenant with your fathers; At the end of the seven years ye shall let go every one his manservant, and every one his maidservant., Verses 14 and 10 (Ramban combined here parts of these verses). And on account of its violation, G-d decreed the exile,, Verses 17-22. just as the Torah decreed exile for the Sabbatical rest of the land which was not observed, as I will yet write,, 25:2. with the help of the Rock.
When He finished stating the ordinance of this [first] commandment as it applies to Hebrew servants, He began the ordinance of the commandment, Thou shalt not murder, since it is the worst [sin] and then [He stated the ordinances of the commandments] to honor one’s parents, and of Thou shalt not steal, and then He went back to the ordinance of one who smites his fellow-man but did not kill him, and then to the murder of a bondman, which is worse than the killing of an offspring, and after that to [injury to] the limbs of Israelites and bondmen,, Verses 24-27. and then to cases of death inflicted by cattle which cause injury., Verses 28-32. All the sections are thus arranged in logical sequence and in proper order.

כי תקנה עבד עברי, the Torah speaks about a Jewish thief who did not have enough money to make restitution (compare Exodus 22,2, “if he is unable to make restitution he will be sold in settlement of what he stole.”) שש שנים יעבוד, this applies to the thief who was sold by the court. The case of someone who had to sell himself (his labour) is discussed by the Torah in Leviticus 25,39 under the heading of כי ימוך אחיך ומכר לך, “when your brother has fallen on economically hard times so that he had to sell himself to cover his debts, etc.” Concerning that situation the Torah adds that he goes free in the Jubilee year (verse 40 there) In our situation, the term he is sold for is 6 years. Some of our sages (Kidushin 14) hold that both situations are halachically similar based on a gezeyrah shavah, identical wording being used by the Torah in both examples, i.e. the word in question being the unnecessary word יעבוד in Leviticus 25,40.

ובשביעית, the seventh year after he was sold, not the seventh year of the Shmittah cycle.

יצא לחפשי, the word lachofshi, a participle of a verb, means “without having to pay compensation;” had the word described the state of liberty of the “servant” now released, the word should have been vocalised lechofshi with the semi vowel sheva under the letter ל.

כי תקנה עבד עברי, “if you acquire a Hebrew servant;” according to Rashi, the scenario described here is that a thief who did not have the means to compensate his victim for what he had stolen, has been “sold” (i.e. the value of his labour for six years) by the court which had convicted him. [A Jew’s body cannot be sold by any court. Ed.] The procedure has been described in Exodus 22,2. Alternately, the person described in the Torah here has fallen on hard times and has sold his labour for six years to a “master” in order to pay off his creditors. If he had been “sold” by the court he does not automatically leave his master’s employment at the conclusion of six years service. Thus far Rashi on above verse. The problem is what prompted Rashi to write that someone sold by the court does not automatically conclude his service at the end of six years? We have a verse in Deuteronomy 15,12, according to which if someone who is a Jew or Jewess, has been “sold” to you, his contract is valid for six years be he a male or a female. He is to be released at the end of that period, and his master is to provide him with a minimal stake to enable him to establish himself economically from that point. (verses 13-14 there) Clearly, that verse and its provisions do not apply to someone who had “sold” himself but had been “sold” by the court. Rashi there also comments that the person in question had been sold by someone other than himself. We must assume therefore that Rashi was explaining the commentary of the Mechilta, according to which the words: כי תקנה apply to the son or daughter of the original master, who had died during these years. The question is whether the contract can be inherited by the master’s children, or in the event that the master did not leave behind any children, whether whosoever inherits the master’s estate this includes the unexpired period of such a servant’s contract. In the event that such a servant had been “sold” by the court would the contract expire automatically with the death of the original purchaser? The wording in Deuteronomy, כי ימכר לך, “if he has been sold to you,” as is distinct from the wording in our verse where the master is described as actively acquiring the servant, i.e. כי תקנה, suggest that the two situations described are not identical. In Deuteronomy the period of service is spelled out as being six years, adding that in the seventh year such a servant has to be released unconditionally, whereas in Exodus, in our verse the …