וכאן שהורתו שלא בקדושה ולידתו בקדושה

And here it is referring to a case where he was not conceived in sanctity, i.e., his mother conceived him before she converted, and only his birth was in sanctity, as she converted when pregnant. It is appropriate to return money to this individual.

רב חייא בר אבין א"ר יוחנן עובד כוכבים יורש את אביו דבר תורה דכתיב (דברים ב, ה) כי ירושה לעשו נתתי את הר שעיר ודלמא ישראל מומר שאני אלא מהכא (דברים ב, ט) כי לבני לוט נתתי את ער ירושה

Rav Ḥiyya bar Avin says that Rabbi Yoḥanan says: By Torah law a gentile inherits from his father, as it is written: “Because I have given mount Seir to Esau as an inheritance” (Deuteronomy 2:5). The Gemara asks: But perhaps it is different with regard to an apostate Jew? In other words, it is possible that Esau was not considered a gentile but rather Jewish, like the Patriarchs. Consequently, he is categorized as an apostate Jew. Rather, the proof is from here: “Because I have given Ar to the children of Lot as an inheritance” (Deuteronomy 2:9), and the descendants of Lot were certainly gentiles.

ורב חייא בר אבין מאי טעמא לא אמר כרבא מי כתיב (ויקרא כה, נ) וחשב עם קונהו ולא עם יורשי קונהו

The Gemara asks: And Rav Ḥiyya bar Avin, what is the reason that he did not state his opinion in accordance with the explanation of Rava, who derives the inheritance of gentiles from the verse: “And he shall reckon with his purchaser” (Leviticus 25:50)? The Gemara answers: Is it written explicitly in the Torah: And he shall reckon with his purchaser and not with the heirs of his purchaser? This proof is based on an exposition, not on an explicit source.

ורבא מאי טעמא לא אמר כרב חייא בר אבין משום כבודו דאברהם שאני :

The Gemara further asks: And Rava, what is the reason that he did not state his opinion in accordance with the explanation of Rav Ḥiyya bar Avin? The Gemara answers: Perhaps due to the honor of Abraham it is different. It is possible that for the sake of Abraham an inheritance was given to the members of his family. The same may not apply to gentiles in general.

תנו רבנן יש בעברי שאין בעבריה ויש בעבריה שאין בעברי יש בעברי שהוא יוצא בשנים וביובל ובמיתת האדון מה שאין כן בעבריה ויש בעבריה שהרי עבריה יוצאה בסימנין ואינה נמכרת ונשנית ומפדין אותה בעל כורחו מה שאין כן בעברי :

§ The Sages taught: There are details of the halakhot of a Hebrew slave that do not apply to the case of a Hebrew maidservant and there are details of the halakhot of a Hebrew maidservant that do not apply to a Hebrew slave. The baraita elaborates: There are unique details in the halakhot of emancipating a Hebrew slave, as he leaves through serving a term of six years, and he leaves through the Jubilee Year, and he leaves through the death of the master, which is not the case for a Hebrew maidservant. And there are unique details in the halakhot of emancipating a Hebrew maidservant, as a Hebrew maidservant leaves through signs indicating puberty, and she is not sold for a second time, and one can redeem her against his will, as the Gemara will explain, which is not the case for a Hebrew slave.

אמר מר יש בעברי שאין בעבריה ורמינהי יתירה עליו אמה העבריה שקונה עצמה בסימנין אמר רב ששת כגון שיעדה

The Gemara analyzes this baraita. The Master said above: There are details of the halakhot of emancipating a Hebrew slave that do not apply to the case of a Hebrew maidservant. And the Gemara raises a contradiction from the mishna: A Hebrew maidservant has one mode of emancipation more than him, as she acquires herself through signs indicating puberty. The expression: More than him, indicates that all of the modes through which a Hebrew slave can be freed apply to a Hebrew maidservant as well. Rav Sheshet said: This baraita is referring to a case where the master designated her to marry him during the six years. Consequently, she cannot be released from his authority by all of the modes through which a Hebrew slave can be freed, as she is his wife.

יעדה פשיטא גיטא בעיא מהו דתימא לא ליבטלה הילכתא מינה קמ"ל אי הכי אמאי יוצאה בסימנין ה"ק אם לא יעדה יוצאה אף בסימנין :

The Gemara asks: If he designated her, it is obvious that she cannot be released in the manner of a slave, as she is his wife and therefore requires a bill of divorce. The Gemara says: It is necessary to state this explicitly, lest you say that the primary halakha is not nullified with regard to her, i.e., even after she has been designated she can still be freed as a slave would be, without a bill of divorce. Therefore, the baraita teaches us that this is not the case. The Gemara asks: If so, that this is referring to a case where he designated her, why does she leave through signs indicating puberty? If he designated her she becomes his wife, and signs indicating the onset of puberty should not affect her status. The Gemara answers: This is what the baraita is saying: If he did not designate her, she leaves also through signs indicating puberty.

ואינה נמכרת ונשנית : מכלל דעבד עברי נמכר ונשנה והתניא (שמות כב, ב) בגניבתו ולא בכפילו בגניבתו ולא בזממו בגניבתו כיון שנמכר פעם אחת שוב אי אתה רשאי למוכרו

§ The baraita teaches: And a Hebrew maidservant is not sold a second time. The Gemara comments: From the fact that the baraita says this about a Hebrew maidservant, it can be inferred that a Hebrew slave can be sold a second time. But isn’t it taught in a baraita that the verse: “And he is sold for his theft” (Exodus 22:2), means that he can be sold to pay for the items that he has stolen but not to pay for his double payment? Although one can be sold into slavery to reimburse the owner for the principal of his theft, he cannot be sold to pay the fine. Furthermore, “for his theft” indicates: But not to pay for his conspiring testimony. If he is a conspiring witness, who is required to pay the value of what he testified that another had stolen but he does not have the money to do so, he is not sold as a slave. Additionally, the phrase “for his theft” teaches that he can be sold for stealing only once, and once he has been sold one time you may not sell him again.

אמר רבא לא קשיא כאן בגניבה אחת כאן בשתי גניבות

Rava said: This is not difficult. Here, in the second baraita, it is referring to one theft, i.e., he stole a large amount but he is not worth enough as a slave for the proceeds of his sale to repay his entire debt. In that case he cannot be sold a second time. There, in the first baraita, it is referring to two thefts, as he may be sold a second time if he stole once, was sold, and subsequently stole again.

א"ל אביי בגניבתו טובא משמע אלא אמר אביי לא קשיא כאן באדם אחד כאן בשני בני אדם

Abaye said to Rava: The expression “for his theft” indicates even many thefts. Rather, Abaye said: This is not difficult. Here, in the second baraita, it is referring to one who stole from one person. This thief cannot be sold a second time even for several thefts. There, in the first baraita, it is referring to thefts from two people.

ת"ר גניבו אלף ושוה חמש מאות נמכר וחוזר ונמכר גניבו חמש מאות ושוה אלף אינו נמכר כלל ר' אליעזר אומר אם היה גניבו כנגד ממכרו נמכר ואם לאו אינו נמכר

The Sages taught: If the property he stole was worth one thousand and as a slave he is worth only five hundred, he is sold and sold again. If the property he stole was worth five hundred and he is worth one thousand, he is not sold at all. Rabbi Eliezer says: If the property he stole was exactly equal to his value if he were sold, he is sold; and if not, he is not sold.

אמר רבא בהא זכנהו ר"א לרבנן דמאי שנא גניבו חמש מאות ושוה אלף דאין נמכר דנמכר כולו אמר רחמנא ולא חציו ה"נ נמכר בגניבתו אמר רחמנא ולא נמכר בחצי גניבתו :

Rava said: In this case Rabbi Eliezer triumphed over the Rabbis, as what is different in a case where the property he stole is worth five hundred and he is worth one thousand that they concede that he is not sold? The reason is that the Merciful One states that he is sold in his entirety, and not part of him. So too, if he is worth less than the value of the property he stole, one can say: The Merciful One states that he is sold for his theft, and he is not sold for part of his theft.

ומפדין אותה בעל כרחו : סבר רבא למימר בעל כרחיה דאדון א"ל אביי מאי ניהו דכתבנא ליה שטרא אדמיה אמאי נקיט מרגניתא בידיה יהיבנא ליה חספא

§ The baraita further teaches: And one can redeem a Hebrew maidservant against his will. Rava thought to say that this means against the will of the master, i.e., she can be redeemed even if he refuses. Abaye said to him: What is the mechanism for emancipating her against the will of her master? Is it that one writes a document to him for her value, and when she has the money she repays this debt? Why should it be possible to force the master to free her in this manner? He is holding a pearl [marganita] in his hand and one gives him a shard instead, as this document is currently useless.

אלא אמר אביי בעל כרחיה דאב משום פגם משפחה אי הכי עבד עברי נמי נכפינהו לבני משפחה משום פגם משפחה הדר אזיל ומזבין נפשיה

Rather, Abaye said: She can be redeemed against the will of her father, due to the family flaw, i.e., the harm caused to the family name by her status. The court pressures the father as much as possible to redeem her, as it is disgraceful to a family if one of its daughters is a maidservant. The Gemara asks: If so, one should force the family of a Hebrew slave to redeem him also, due to the family flaw. The Gemara answers: There is a concern that he will go back and sell himself and earn money in this manner at his family’s expense.

ה"נ הדר אזיל ומזבין לה הא קתני אינה נמכרת ונשנית ומני ר"ש היא דתניא מוכר אדם את בתו לאישות ושונה לשפחות ושונה לאישות אחר שפחות אבל לא לשפחות אחר אישות רש"א כשם שאין אדם מוכר את בתו לשפחות אחר אישות כך אין אדם מוכר את בתו לשפחות אחר שפחות

The Gemara asks: Here too, in the case of a Hebrew maidservant, the father might go back and sell her as a maidservant again and receive money for her a second time. The Gemara answers that it is taught: A maidservant is not sold a second time. And whose opinion is this? It is that of Rabbi Shimon, as it is taught in a baraita: One can sell, i.e., transfer, his young daughter in marriage and go back and betroth her again if she was divorced or widowed. Likewise, he can sell her into slavery and transfer her again, this time for marriage, after he sold her into slavery. But one cannot sell his daughter into slavery after marriage. Rabbi Shimon says: Just as a person cannot sell his daughter into slavery after marriage, so too, a person cannot sell his daughter into slavery after slavery.

ובפלוגתא דהני תנאי דתניא (שמות כא, ח) בבגדו בה

The Gemara comments: And this issue is taught in the dispute between these tanna’im, as it is taught in a baraita with regard to the verse: “He shall have no power to sell her to a foreign people, seeing that he has dealt deceitfully with her [bevigdo vah]” (Exodus 21:8).