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
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, 34:23, 14), and why it is punishable by Galus - like the Shemitah (Ramban).
What is the definition of "Eved Ivri"?
Which would then teach us that he goes out after six years, and the Pasuk "v'Hisnachaltem Osam li'Veneichem" would be confined to an Eved Kena'ani that one purchased from a Nochri (Rashi).
How do we know that the Pasuk is referring to an Eved whom Beis-Din sold because he stole, and not to a poor man who sold himself for funds?
Rashi: "Ki Yamuch" (Vayikra 25:39) already teaches about the latter. Rather, here it discusses one sold to pay his theft - (22:2) "v'Im Ein Lo v'Nimkar bi'Geneivaso".
What are the implications of the double Lashon "Yeitzei la'Chofshi Chinam"?
Rashi: It means that he goes out to freedom free of charge (without having to pay anything).
What is "Shevi'is" referring to?
Rashbam: It is referring to the seventh year following his sale (not the Shemitah year).
Moshav Zekenim: The Parshah can discuss Hashem acquiring Yisrael. A man works for 60 years 1 , and after 70 he dies, and is free of Mitzvos.
Hadar Zekenim: Yisrael will go out to [permanent] freedom from the seventh exile - Bavel 2 , Kasdim, Madai, Yavan, Paras, Yishmael, Edom.
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
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 Kena'ani bought from an Ivri goes free after six years!
Moshav Zekenim: If an Eved Kena'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
Rashi writes 'perhaps it discusses an Eved Kena'ani here.' How can one buy an Eved Kena'ani? It says about them "Lo Sechaye Kol Neshamah"!
Moshav Zekenim #1: 'Kena'ani' is imprecise. All Nochri slaves are called Kena'ani, due to "Arur Kena'an Eved Avadim Yihyeh l'Echav" (Bereishis 9:25).
Moshav Zekenim #2: We must kill only Kena'anim in Eretz Yisrael, but not those outside, and not children of a Kena'anis from a father of a different nation.
Yerushalmi (Shevi'is 6:1): Yehoshua gave to the Kena'anim the option to make peace (and abandon 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 Kena'anim. (PF)
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.
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 Kena'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 Kena'ani here.' How could an Eved Kena'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