What does the Torah mean when it says "Im Ra'ah be'Einei Adonehah ... "?
Rashi (citing Kidushin, 19b): The Torah means to say that she did not find favor in his eyes to betroth her, 1 since the money he paid for her was meant to serve as Kidushin money. 2
Ramban: Once a master says that he will not marry her, her father should redeem her immediately, since the sole objective of selling one's daughter should for marriage.
Why does the Torah write "asher Lo Ye'adah" with an 'Alef'?
Oznayim la'Torah: The Torah is hining here that it prefers the (younger) son - by whom it writes "Yi'adenah" to perform Yi'ud and not the (older) father. 1
Oznayim la'Torah: Based on the Gemara in Yevamos, 101b in connection with Yibum - that if the Yavam is much older or younger than the Yevamah, we advise him to perform Chalitzah.
What are the connotations of the word "asher Lo Ye'adah"?
Kidushin, 19a: It means that he is obligated (from the Lashon'Da'as) 1 that he is betrothing her.
Mechilta: The Mapic 'Hey' in "Ye'adah" teaches us that he is not permitted to make Yi'ud with two Amah ha'Ivriyos simultaneously.
See Torah Temimah, note 70.
What are the connotations of "Vehefdah"?
Rashi, Ramban and Rashbam: It implies that the master helps her father to redeem her, by accepting from him the balance based on how much he paid for her and how many years remain of the six years that he purchased her for. 1
Kidushin, 16a: It teaches us that once the money has been deducted, the girl goes free - that she acquires herself with 'Gera'on Kesef.'
Kidushin, 14b: It teaches us that an Amah ha'Ivriyah is acquired with money.
If for example, he purchased her for a Manah and two years have passed, the father refunds two thirds of a Manah, and she returns home (Rashi).
What are the implications of the phrase "asher Lo Ye'adah Vehefdah"?
Bechoros, 13a: It implies that the Mitzvah of Yi'ud takes precedence over that of Pediyah.
What does the Torah mean when it writes "le'Am Nochri Lo Yimshol ..."?
Rashi: It means that her master and her father may not subsequently sell her to anybody else.
Ramban #1 and Hadar Zekenim: It is a prohibition against a father selling his daughter to a Nochri under any circumstances, 1 for obvious reasons. 2
Ramban #2, Seforno, Targum Onkelos and Targum Yonasan: It refers to her father, who is prohibited from subsequently selling her a second time.
Kidushin, 18b: Refer to 21:8:4:4.
Even though the Torah (in Vayikra 25:47) specifically permits an Ivri to sell himself to a Nochri.
Although Rashi's explanation conforms to the Gemara in Kidushin, 19a, the Ramban queries Rashi's translation of "Am Nochri". (See Ramban, who finally ascribes the Gemara's ruling to the words "be'Vigdo vah", as if it had written "Lo Yimshol" twice).
What is the meaning of "be'Vigdo vah"?
Rashi and Ramban #1: Her master betrayed her by not marrying her, and her father, by selling her 1 to this man [who will not marry her].
Ramban #2 and Seforno 2 : The Torah is coming to prohibit her father from subsequently betraying his daughter by selling her to a Nochri. 3
Rashbam: Her master betrayed her, since he should have married her. 4
Kidushin 18b: Once her master has placed his garment over her (married her), he is not permitted to sell her.
QUESTIONS ON RASHI
Rashi writes that "Vehefdah" teaches that she is redeemed for the value of her remaining labor. We should know this already, because she is equated to an Eved Ivri!
Riva citing Rashba: This teaches that if her father has money, we force him to redeem her against his will, due to blemish to the family.
Riva #1, Hadar Zekenim: An Eved Ivri is redeemed only through money. She can be redeemed even through Shaveh Kesef (Metaltelim). 1
Riva #2: Since it says Hefdah, she must be sold for an amount that allows reduced redemption; she cannot be sold for one Perutah.
Moshav Zekenim: We cannot learn to an Amah, for her father has the right to sell her. 2
Riva: This is wrong. We conclude that also an Eved Ivri can be redeemed even through Shaveh Kesef! Hadar Zekenim - it is fine according to the opinion that for an Amah, Ge'ulah (giving part of the value of the remaining years) with Shaveh Kesef [that later rose in value] can free her later based on the increased value. For an Eved Ivri, it can free only according to its value when he gave it.
Why is this a reason not to have reduced redemption? Perhaps he means that since the Torah gave her father rights to sell her, it should not make leniencies to help others redeem her. (PF)
Rashi writes that he helps her father to redeem her, through accepting the balance based on how much he paid for each year. Why is this called helping? It is proper to pay the value of her remaining labor!
Rosh, Hadar Zekenim, Moshav Zekenim #1: Older girls can do more labor. 1 The value of each remaining year is more than each year that she worked. 2
Moshav Zekenim: The master reduces from the balance based on the remaining years. He cannot pardon the redemption, i.e. totally, but he can pardon part.
Gur Aryeh: The master owns her Guf. Therefore, according to letter of the law, he should not deduct due to the labor she did. 3
Sefer ha'Chinuch, Mitzvah 44: The money paid for the remaining labor was with her [father, and he was able to profit from it]. The master may not take compensation for this.
For very young girls, their labor is worth less than the cost of feeding them! (PF)
Da'as Zekenim says that this is why Rashi calls this Gir'aon Kesef. I do not understand this. Gir'aon merely means reduced. We say that also Eved Ivri is redeemed through Gir'aon Kesef, even though often his first years are worth more than his latter years, e.g. if he is old! (PF) According to Rashi (Kidushin 20a), an Eved Ivri is redeemed based on the current value if the price of labor declined. An Amah is equated to an Ivri, but perhaps not for this, e.g. if in spite of the decline, her current value is now more because she is older.
Just like one who sells a house in a walled city, and redeems it, does not deduct the rental value that the buyer enjoyed, for it was a sale, and not a rental. (PF)