Handl with Care: Should We Negotiate with Terrorists?

Adapted from the writings of Dayan Yitzhak Grossman

July 17, 2025

The New York Times reports:

The Palestinian militant group Hamas said on Friday that it had responded positively to a new proposal for a 60-day Gaza cease-fire with Israel and was ready to immediately enter negotiations on implementing it.

It was not immediately clear whether Hamas was demanding any significant changes to the proposal and whether any gaps could be easily bridged or create new hurdles to an agreement. The two sides have come close before to such agreements, only to see them unravel at the last minute over the details…

The proposal calls for hostage-for-prisoner swaps and negotiations leading to a permanent end to the nearly two-year-old war in Gaza.[1]

As we have previously discussed in this forum, there is extensive halachic discussion, beginning in the Mishnah, of the permissibility of paying exorbitant ransoms for prisoners, which in the modern era has expanded to include the question of prisoner exchanges. The primary focus of this discussion is the concern that rewarding and incentivizing kidnapping will cause more of it.

Redeeming captives for too much

The Mishnah declares that we do not redeem captives for more than their value.[2] The Gemara gives two reasons for the prohibition: either to avoid excessively burdening the community, or to avoid providing an incentive for the repetition of such seizures. Most poskim accept the latter reason as normative,[3] but some consider the matter unresolved.[4]

Voluntary redemption

The Gemara explains that a point of divergence between the two reasons is where someone voluntarily offers an excessive ransom for his relative: The former reason does not apply, while the latter does.[5] Though there is an opinion that limits such volunteering (even according to the first reason) to a relative,[6] other authorities reject this distinction[7] and permit even the community to pay an excessive ransom, as long as it does so voluntarily and not under compulsion by community leadership.[8]

Determining value

One interpretation of the “value” of a captive is what he would sell for in a slave market, and if there is no local slave market, we estimate his value to a slaver who would transport him to a locale where such a market exists.[9] Others interpret “value” in light of the need to avoid incentivizing future seizures, so they understand the rule to mean simply that we do not pay more than what is typically paid, as that would engender a particular interest in capturing Jews.[10]

Indiscriminate captors

Various poskim suggest that in the context of indiscriminate captors—such as during the era of the Churban, when all the Jews were subject to capture[11]—or when dealing with captors who assume no risk and therefore indiscriminately seize anyone, irrespective of the possibility of ransom,[12] the concern of incentivizing future seizures does not apply.

Some argue that modern-day terrorists, who anyway do whatever harm they possibly can, fall under this rubric.[13] Others say that yielding to the demands of terrorists will indeed encourage further terrorism, whereas refusing them will cause them to cease their outrages.[14]

Danger to life

Many poskim rule that when a captive’s life is in danger, he may be redeemed at any cost,[15] but many others disagree.[16] Where a particular terrorist group has a track record of making deals to release its prisoners, it is not entirely clear whether the halacha would consider those prisoners to be in mortal danger (at least not more so than prisoners in general, who are not considered, in our context of paying exorbitant ransoms, to be in such danger).

Hostage-terrorist exchanges

Contemporary poskim in Eretz Yisrael have vigorously debated the propriety of exchanging captured terrorists for hostages held by the enemy, in particular in the context of the (ultimately unsuccessful) negotiations that preceded Operation Entebbe and the controversial and traumatic Jibril Agreement. Some forbade such exchanges, based on the aforementioned concerns as well as additional arguments, including the claim that in war, combat, not dealmaking, is the appropriate mode of conduct.[17] Others endorsed them, on the grounds that the lives of the hostages were in danger,[18] and that the terrorists will do their worst regardless, as above.[19]

The freeing of terrorists obviously poses an additional dilemma, due to the grave threat to society of their likely recidivism. Some poskim argued that exchanges are nevertheless permitted, at least where the immediate danger to the hostages is clear and present and the future danger to the public is speculative and indefinite.[20] Others disagreed, maintaining that even if the hostages are in certain mortal peril, we cannot save them at the cost of putting the lives of others at risk.[21] Moreover, some argued, as above, that even the payment of monetary ransoms to terrorists is fundamentally misguided, for the paradigm of pidyon shvuyim is inapplicable to terrorist hostage-taking. It applies only during peacetime—not in wartime, where the provision of large sums of money (and presumably, a fortiori, the release of veteran terrorists) to the enemy will aid him in his hostilities.[22]

Some have argued that because terrorists are commonly exchanged for hostages, offering such an exchange at the customary ratio would not be considered redeeming the hostages for more than their value.[23]

[1]Adam Rasgon and Ephrat Livni. Hamas Says It Is Ready to Negotiate Truce Proposal. The New York Times. https://www.nytimes.com/2025/07/04/world/middleeast/hamas-israel-ceasefire.html.

[2]Gittin 45a.

[3]Yad Hachazakah Hilchos Matnos Aniyim 8:12; Radvaz ibid.; Kessef Mishneh ibid.; Ramban and Rashba to Gittin ibid.; Shulchan Aruch Y.D. siman 252:4.

[4]Ran ibid. Shu”t Nachalah Lihoshua siman 5 argues that even according to the Ran, where the latter reason does not apply, redeeming for any price is the appropriate course of action. Cf. Shu”t Bnei Vanim cheilek 1 siman 43 os 2 p. 150 for an exhaustive list of the opinions of the Rishonim on this question.

[5]Gittin ibid. and Rashi there.

[6]“Chacham echad” cited in the Nachalah Lihoshua ibid.

[7]The Nachalah Lihoshua (himself) ibid.

[8]Shu”t HaRadvaz cheilek 1 siman 40; Nachalah Lihoshua ibid. (One of the Radvaz’s various justifications of the customary payment of excessive ransoms is based on the fact that the communities gladly pay it; the implication is that this justifies the overpayment even according to the latter reason, which he considers normative. But see Shma Avraham cheilek 1 end of siman 12 p. 47a s.v. Umatsasi, who argues that the Radvaz only advances this reason in concert with his others, but it does not stand on its own.)

[9]Shu”t Maharam Lublin siman 15. Cf. Pis’chei Teshuvah ibid.

[10]Shu”t HaRadvaz ibid. Cf. Bnei Vanim ibid. at length.

[11]Tosfos, Ramban and Me’iri ibid.

[12]Nachalah Lihoshua ibid.

[13]R’ Yosef Shalom Elyashiv, as cited by his son-in-law R’ Yitzchak Zilberstein in Shoshanas Ha’amakim (Bnei Brak 5759), Verapo Yerapei p. 113; Shu”t Yabia Omer cheilek 10 C.M. siman 6 (a version of this teshuvah was first published in Torah Shebe’al Peh #19 (5737), “Mivza Entebbe Bahalacha” pp. 9-39); Shu”t Asei Lecha Rav cheilek 7 siman 53 pp. 229 and 232 (the latter describes his position as tentative, as such novel ideas must be endorsed by poskim at the highest level).

[14]The Steipler Gaon (R’ Yaakov Yisrael Kanievsky), as cited in Orchos Rabeinu, Sipurim Shonim os 20 p. 367.

[15]Tosfos ibid. 58a and in Piskei Tosfos os 216; Me’iri ibid.; Shu”t Mahari Bruna siman 236; Yam Shel Shlomo ibid. simanim 68 and 72; Eirech Lechem Y.D. ibid.; Bais Hillel Y.D. ibid. os 2 (who mentions that the Maharshak (R’ Shmuel Kaidanover) also held this way); Bais Dovid (Salonika) Y.D. siman 120; Sdei Chemed-Divrei Chachamim end of siman 77; Yabia Omer ibid.; Rav Zilberstein ibid., who reports that his father-in-law, Rav Elyashiv, held this way.

[16]Ramban ibid.; Maharam Lublin ibid.; Knessess Yechezkel ibid.; Yad Eliyahu ibid.; Bnei Vanim ibid. p. 153, and cf. Shu”t Tzemach Tzedek siman 28 in the author’s son’s note; Pis’chei Teshuvah ibid.; and Sdei Chemed klalim cheilek 1 ma’areches ha’aleph os 129. (The Sdei Chemed-Divrei Chachamim points out that the Maharam’s entire discussion technically revolves around the question of an obligation to redeem a captive whose life is in danger for more than his value—not whether this is permitted—but he argues that given that the Maharam insists that the rule of ein podin es hashvuyin yoseir al kedei demeihen remains applicable, redemption would presumably not only not be mandatory, it would be forbidden.)

See the discussions in Shma Avraham (p. 43a), Yabia Omer, Sdei Chemed-Divrei Chachamim, Bnei Vanim and R’ Yehuda Gershuni, Pidyon Shvuyim Le’or Hahalacha, Hadarom #33 (Nisan 5731) pp. 27-31 for lengthy and intricate treatments of this question, including the citation of numerous additional sources.

[17]R’ Shlomo Aviner (here, here and here), invoking R’ Yaakov Kamenetsky’s rejection of a contemplated deal on behalf of R’ Yitzchok Hutner during the Dawson’s Field hijackings. R’ Yaakov explained that “in war, there is no din of pidyon shvuyim, but rather a din of battle.” Cf. below n. 22.

[18]Rav Elyashiv and the Steipler ibid.

[19]See note 12.

[20]Yabia Omer ibid.

[21]Rav Gershuni ibid. pp. 32-37.

[22]R’ Yaakov during the Dawson’s Field hijackings (see above n. 17), as cited by R’ Hershel Schachter in Or Hamizrach Volume 37 (5749) p. 20. Cf. Dr. Michael Vigoda, Pidyon Shvuyim–Lo Bechol Mechir.

[23]Bnei Vanim at the beginning of the siman; R’ Avraham Yitzhak Kilav, Techumin Vol. 4 (seen secondhand).