Redeeming Captives

(14) When Abram heard that his kinsman’s [household] had been taken captive, he mustered his retainers, born into his household, numbering three hundred and eighteen, and went in pursuit as far as Dan. (15) At night, he and his servants deployed against them and defeated them; and he pursued them as far as Hobah, which is north of Damascus. (16) He brought back all the possessions; he also brought back his kinsman Lot and his possessions, and the women and the rest of the people.

(1) When the Canaanite, king of Arad, who dwelt in the Negeb, learned that Israel was coming by the way of Atharim, he engaged Israel in battle and took some of them captive. (2) Then Israel made a vow to יהוה and said, “If You deliver this people into our hand, we will destroy (dedicate the spoils) their towns. (3) יהוה heeded Israel’s plea and delivered up the Canaanites; and they and their cities were proscribed. So that place was named Hormah.

(1) By the time David and his men arrived in Ziklag, on the third day, the Amalekites had made a raid into the Negeb and against Ziklag; they had stormed Ziklag and burned it down. (2) They had taken the women in it captive, low-born and high-born alike; they did not kill any, but carried them off and went their way. (3) When David and his men came to the town and found it burned down, and their wives and sons and daughters taken captive, (4) David and the troops with him broke into tears, until they had no strength left for weeping. (5) David’s two wives had been taken captive, Ahinoam of Jezreel and Abigail wife of Nabal from Carmel. (6) David was in great danger, for the troops threatened to stone him; for all the troops were embittered on account of their sons and daughters.
But David sought strength in the LORD his God. (7) David said to the priest Abiathar son of Ahimelech, “Bring the ephod up to me.” When Abiathar brought up the ephodaSee note at 2.28. to David, (8) David inquired of the LORD, “Shall I pursue those raiders? Will I overtake them?” And He answered him, “Pursue, for you shall overtake and you shall rescue.” (9) So David and the six hundred men with him set out, and they came to the Wadi Besor, where a halt was made by those who were to be left behind.

Rava said to Rabba bar Mari: Concerning this matter that the Sages stated, that redeeming captives is a great mitzva, from where is it derived? Rabba bar Mari said to him: As it is written: “And it shall come to pass, when they say to you: To where shall we depart? Then you shall tell them: So says the Lord: Such as are for death, to death; and such as are for the sword, to the sword; and such as are for famine, to famine; and such as are for captivity, to captivity” (Jeremiah 15:2). And Rabbi Yoḥanan says: Whichever punishment is written later in this verse is more severe than the one before it.

(10) The redemption of captives receives priority over sustaining the poor and providing them with clothing. [Indeed,] there is no greater mitzvah than the redemption of captives.30For as the Rambam continues to explain, all of the different aspects of charitable gifts are included in the redemption of captives (Bava Batra 8b). For a captive is among those who are hungry, thirsty, and unclothed and he is in mortal peril.31For at any time, his captors may take his life. If someone pays no attention to his redemption, he violates the negative commandments: "Do not harden your heart or close your hand" (Deuteronomy 15:7 , "Do not stand by when the blood of your neighbor is in danger" (Leviticus 19:16 , and "He shall not oppress him with exhausting work in your presence" (ibid. 25:53). And he has negated the observance of the positive commandments: "You shall certainly open up your hand to him" (Deuteronomy 15:8 , "And your brother shall live with you" (ibid. 19:18), "Love your neighbor as yourself" (Leviticus 19:18 , "Save those who are taken for death" (Proverbs 24:11 , and many other decrees of this nature. There is no mitzvah as great as the redemption of captives.

The captives are not redeemed for more than their actual monetary value, for the betterment of the world; and one may not aid the captives in their attempt to escape from their captors for the betterment of the world, so that kidnappers will not be more restrictive with their captives to prevent them from escaping. Rabban Shimon ben Gamliel says: For the betterment of the captives, so that kidnappers will not avenge the escape of the captives by treating other captives with cruelty.

[Tosfot quotes the Gemara:] "for whatever [amount of] money that they demand." [He was legally allowed to do this because where] there is a threat to life, we redeem the captives for more than their value. [This is like what] we say in Chapter 'Hasholeach' (above, page 47a) about one who sells themselves and their children to idol-worshippers, [and this is true] a fortiori here where there is a murderer. Alternatively, [he was allowed to redeem the baby for more than its worth] because [it possessed] great wisdom.

דלא ליגרבו ולייתו—They should not seize and bring

OVERVIEW
The משנה ruled that we should not redeem captives for more than they are worth. The גמרא asked, is it because it will place a greater burden on the community to pay for their redemption (so if an individual wants to redeem someone he may do so), or is it because this will cause the gentiles to seize more and more people (in which case even an individual may not redeem for more than the value). תוספות reconciles this latter view with seemingly contradictory גמרות.
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תוספות anticipates a difficulty:
והא דתניא בפרק נערה (כתובות נב,א) נשבית והיו מבקשין ממנה עד עשרה בדמיה –
And this which the ברייתא taught in פרק נערה, ‘if one’s wife was captured and they wanted ten times her value in order to release her –
פעם ראשון פודה –
The first time it happens he should redeem her’; this would seemingly contradict this view of דלא ליגרבו!
תוספות replies:

שאני אשתו דהויא כגופו יותר מבתו דהכא –
His wife is different (than all other captives) for she is like his own body, even more so than the case of the daughter mentioned here, so since she is כגופו –
ועל עצמו לא תיקנו שלא יתן כל אשר לו בעד נפשו –
There was never an enactment that regarding one’s self he should not give whatever he possesses for himself, rather there is no limit; the same applies to אשתו.
תוספות anticipates another difficulty:
ורבי יהושע בן חנניא דפרקיה לההוא תינוק בממון הרבה בהניזקין (לקמן דף נח,א) –
And regarding ריב"ח who redeemed that child for much money, which is mentioned in פרק הניזקין, how was he permitted to do so if we assume דלא לגרבו?
תוספות responds:

לפי שהיה מופלג בחכמה אי נמי בשעת חורבן הבית לא שייך דלא ליגרבו :
For he was exceedingly bright, or you may also say that during the time of the destruction of the ביהמ"ק, the reason of 'לא ליגרבו', does not apply.