Shalom R' Mordechai,

Thank you for your timely and important question.

I am not familiar with the state of public discourse in the United States or how the rabbinic leadership there is responding, but here in Israel the discussion is very present, and the sources you cited are frequently quoted, although not always in the proper context or with accurate interpretation.

I am not qualified to issue Halachic rulings, and certainly not on a matter so weighty and heartbreaking. I can only offer a brief overview of several sources that illustrate how this issue has never been simple, and that the words of the Gemara were not accepted at face value. I believe the following sources may help shed some light on the proper Halachic approach to the matter.

A) In Gitin 45a, we learn that one may not redeem captives for more than their value, because of Tikun ha'Olam, nor may one rescue them by escaping them from their captors, also due to Tikun ha'Olam. Raban Shimon ben Gamliel explains that the reason is to avoid harsher treatment of other captives who remain behind. The Gemara there questions the nature of this Tikun ha'Olam: is it due to the financial burden on the community, or due to the concern that high ransoms will encourage more kidnapping? The Gemara leaves the question unresolved.

B) The Shulchan Aruch (Yoreh De'ah 252) cites this Gemara and strongly encourages the redemption of captives, but introduces certain qualifications. He states that a person may redeem himself for any amount he desires. Similarly, a Talmid Chacham may be redeemed even for more than his value. This is also true for a "Talmid Charif," a gifted student with the potential to become a great scholar in the future.

C) The Be'er Heitev records a dispute between the Shach and the Taz regarding whether one may redeem close relatives for more than their value, as one may do for oneself. He adds that one certainly redeems his wife at any cost, and concludes that this is the common custom (Minhag ha'Olam).

D) In Gitin 58a, there is a well-known story of Rebbi Yehoshua ben Chananya who went to Rome and found a young boy in captivity. Realizing the child's great potential to become a Torah leader, he said he is willing to redeem the boy for "any money in the world," and redeemed him for a large sum. That child eventually became Rebbi Yishmael ben Elisha, the Kohen Gadol.

E) Tosfos there explains that Rebbi Yehoshua was permitted to pay any price either because the child was in danger of death, or because, as we already saw, even one with the potential to become a Talmid Chacham may be redeemed at a high cost, unlike an "ordinary" person.

F) In Mishnah Terumos (8:12), and especially in the Yerushalmi there, we find that if non-Jews demand even a specific individual to be handed over for execution, under threat of killing the entire community, he may not be handed over unless he is already liable for the death penalty. This teaches that even to save many people in the future, one may not actively deliver up a particular person. The public is not permitted to "sacrifice" an individual for the sake of the community. This, of course, refers to a case where the community itself would actively hand over the individual, not one where the captors already seized him.

G) In Shu"t Ru'ach Chayim (Yoreh De'ah 252:2) by Rav Chayim Palagi, he describes an incident in Izmir where kidnappers demanded an excessive ransom for Jewish captives. The question was whether neighboring communities could be compelled to contribute. He praises those who volunteer to give, recognizing the great Mitzvah of Pidyon Shevuyim.

H) In Shu"t Radbaz (1:40), he writes that it has become customary to redeem captives even beyond the standard price. If there are donors willing to pay, certainly the redemption should proceed, especially when children are involved, since they might be forced to convert, violate Shabbos, or endure suffering worse than death. Although he raises the question from the Gemara in Gitin, he answers that if the community chooses to act out of desire and willingness, it is permitted. He blesses those who do so. He also tells the story of the Maharam of Rottenburg, who refused to be redeemed for more than the standard price, despite being a great Talmid Chacham, which perplexes the Radbaz.

I) Around the time of the Entebbe hijacking in 1976, later known as Operation Entebbe, there were serious deliberations among prominent Poskim including Rav Elyashiv zt'l and Rav Ovadyah Yosef zt'l in Israel. Many ruled that releasing terrorists was permitted in order to save the hostages, since it was clear that otherwise the captors would kill them. The argument was that this was a case of certain Piku'ach Nefesh, as opposed to uncertain or delayed danger.

J) In 1970, during the hijacking of a passenger plane to Jordan, which included Rav Yitzchak Hutner zt'l, Rav Moshe Feinstein zt'l wrote a letter to the Prime Minister of Israel, Golda Meir. He supported the release of terrorists in exchange for the hostages, echoing the position a few years later expressed by other Poskim.

A careful review of the sources, alongside a historical survey, shows many exceptions to the strict ruling of the Gemara. It appears that the Jewish communities throughout history acted with great compassion, redeeming captives repeatedly even at prices above their assessed value. Of course, every case must be considered individually and seriously. But it is clear that the matter is deeply complex, and certainly not a simple black-and-white issue.

I hope this helps a bit,

Aharon Steiner