Why does the Torah begin Mishpatim with the Parshah of Eved Ivri?
Ramban: Because setting him free in the seventh year commemorates a. Yetzi'as Mitzrayim - which in turn, is mentioned in the first of the Aseres ha'Dibros, and b. Ma'aseh Bereishis, 1 the two doundations of Emunah.
Since he is set free from work when the seventh year arrives - and this is reminiscent of the Shabbos - which also commemorates the Creation - Ramban, as well as Yetzi'as Mitzrayim. Refer to 13:16:3:2*. And it is for these reasons that the Navi portrays the issue of Eved Ivri in the strictest of terms - see Yirmiyah, 34:13 & 14, and why it is punishable by Galus - like the Shemitah (Ramban).
What is the definition of "Eved Ivri"?
Rashi: It means an Eved who is an Ivri, since the Pasuk in Ki Seitzei, Devarim (22:2) refers to him as "Achicha" (he is not an Eved Cana'ani that one purchased from an Ivri). 1
Which would then teach us that he goes out after six years, and the Pasuk "ve'Hisnachaltem osam li'Veneichem" would be confined to an Eved Cana'ani that one purchased from a Nochri (Rashi).
Why does the Torah here refer to him as "Eved", and in B'har Vayikra 25:39, as "Achicha"?
Mechilta: To teach us that that, on the one hand, the master must treat him like a brother, 1 whereas on the other, the Eved must behave like an Eved.
Oznayim la'Torah: Because the Pasuk in B'har is speaking about someone who, having dealt with Sh'mitah produce, became poor, sold himself, and who moreover, had already suffered various degrees of poverty, is still considered a full-fledged 'Achicha', whereass the current Parshah is speaking about someone who is sold because he stole, thereby lowering himself to a degree, to the status of an Eved Cana'ani, 2 - a fitting partner for a Shifchah Cana'anis.
Why does the Torah insert the word "Eved"?
Sifri (in Re'ei): To teach us that, when purchasing an Eved, one should give precedence to an Eved Ivri over an Eved Cana'ani. 1
What sort of Eved Ivri is the Torah referring to? Why is he being sold?
Rashi: It is referring to an Eved who is being sold to pay for what he stole - "ve'Im Ein lo, ve'Nimkar bi'Geneivaso" (22:2). Because the Din of an Eved who sold himself we know from "Ki Yamuch Achicha" in B'har, Vayikra 25:39.
What does the assertive Lashon "Sheish Shanim Ya'avod" (rather than 've'Avad Sheish Shanim') teach imply?
Kidushin, 17a: It implies a. that if he fled in the middle, he is obligated to complete the six years upon his return, and b. that if his master dies, he is obligated to serve his son for the remaining period. 1
See Torah Temimah, note 24.
What can we learn from the juxtaposition of "u'va'Shevi'is" to "Sheish Shanim Ya'avod"?
Erchin, 18b: We can learn that sometimes, the Eved Ivri works into the seventh year - because the six years are 'Me'eis le'Eis' (six complete years, by the time on the clock).
Yerushalmi, Kidushin, 1;2: We can learn that the Eved must work up until the last second of the sixth year, and that he only goes free at the beginning of the seventh.
Yerushalmi Kidushin, 1;2: It teaches us that the Eved Ivri goes free in the seventh year following his sale and not in the Sh'mitah year.
What is "Shevi'is" referring to?
Rashbam: It refers to the seventh year following his sale (not the Sh'mitah year). 1
Moshav Zekenim: The Parshah can discuss Hashem acquiring Yisrael. A man works for 60 years 2 , and after 70 he dies, and is free of Mitzvos.
Hadar Zekenim: Yisrael will go out to [permanent] freedom from the seventh exile - Bavel 3 , Kasdim, Madai, Yavan, Paras, Yishmael, Edom.
Refer also to 21:2:3.2:3.
I do not know the source to say that "Shanim" refers to decades. (PF)
It seems that it should say 'Mitzrayim' in place of Bavel or Kasdim, for they are one and the same! (PF)
What are the implications of the double Lashon "Yeitzei la'Chofshi Chinam"?
Rashi and Mechilta: It means that he goes out to freedom free of charge (without having to pay anything [and does not require a Get Shichrur - Mechilta]). 1
Rambam (Avadim, 2:12): We learn from the word "Chinam" that if he is sick (even for the duration of the six years) and even if his illness incurred many expenses for his master, he goe free at the end of six years.
Oznayim la'Torah: Even according to the opinion that his master acquires him with a Kinyan ha'Guf, and even if the money he received for his purchase is not sufficeint to pay for what he stole. See also Torah Temimah, note 25.
It says that he works for six years. Why must it teach that in Shevi'is, he goes free?
Moshav Zekenim: Even if he was sick all six years and did not work, he goes free. 1
QUESTIONS ON RASHI
Rashi writes that "Ki Yamuch" already teaches about one who sells himself due to poverty, so here it discusses one sold to pay his theft. "Ki Yamuch..." teaches only that he goes free in Yovel. Some say that he does not go free after six years! (Moshav Zekenim)
Divrei David: "Ki Yamuch" implies that one who sold himself works for as long as the buyer paid, unless Yovel comes first. Therefore, here we discuss one that Beis Din sold.
Rashi writes that here it discusses an Eved who is an Ivri, since Devarim (15:12) calls him "Achicha". Perhaps here it teaches that even an Eved Cana'ani bought from an Ivri goes free after six years!
Moshav Zekenim: If an Eved Cana'ani bought from an Ivri goes free after six yeara, we would not need a verse to teach the same for an Ivri bought from an Ivri.
Moshav Zekenim citing his Rebbi: "Ki Yimacher... Achicha" excludes a Cana'ani.
Moshav Zekenim citing Mechalel: "Ha'Ivri" (Devarim 15:12) is free for a Gezeirah Shavah to teach that also here discusses an Ivri.
Rashi writes 'perhaps it discusses an Eved Cana'ani here.' How can one buy an Eved Cana'ani? It says about them "Lo Sechaye Kol Neshamah"!
Moshav Zekenim #1: 'Cana'ani' is imprecise. All Nochri slaves are called Cana'ani, due to "ArurCana'an Eved Avadim Yihyeh l'Echav" (Bereishis 9:25).
Moshav Zekenim #2: We must kill only Cana'anim in Eretz Yisrael, but not those outside, and not children of a Cana'anis from a father of a different nation.
Yerushalmi (Shevi'is 6:1): Yehoshua gave to the Cana'anim the option of making peace (and abandoning their idolatry, and they may live in Eretz Yisrael). 1
This does not fully answer the question, for no nation made peace, yet the Mishnah and Gemara discuss Avadim Cana'anim. (PF)
Rashi writes that one might have thought that one who Beis Din sells does not go free after six years. Devarim 15:12 discusses one sold through Beis Din, and says that he works for six years!
Da'as Zekenim, Hadar Zekenim: We need two verses to teach an inclusion and an exclusion - if the master died, one sold through Beis Din works the rest of the six years for a son [who inherited the master], but not for a brother.
Riva: We know that Devarim discusses one sold through Beis Din based on the conclusion here.
Rashi writes that "v'Hisnachaltem Osam li'Veneichem" would apply to an Eved Cana'ani bought from a Nochri. Nochrim cannot buy slaves from Yisrael (Yevamos 46a)!
Hadar Zekenim #1: We discuss a Nochri who sold himself to a Yisrael.
Hadar Zekenim #2, Riva #1: We conclude there that a Nochri can buy a slave for his labor, just he does not acquire him bodily.
Riva #2: Nochrim can acquire slaves from Yisrael in war - "va'Yishb Mimenu Shevi" (Bamidbar 21:1).
Rashi writes 'perhaps it discusses an Eved Cana'ani here.' How could an Eved Cana'ani be Nirtza? His ear did not hear on Sinai "Ki Li Bnei Yisrael Avadim"!
Riva, citing R"M of Kutzi: One might have thought that he is Nirtza even though his ear did not hear... because he is lower than an Eved Ivri.