3,195. When We Don't Redeem Captives
Hilchos Matnos Aniyim 8:12
Captives aren’t redeemed for exorbitant sums for the benefit of society (literally, tikkun ha'olam), i.e., to remove the motivation for enemies to abduct people for ransom. We don’t help captives to escape, also for the benefit of society (tikkun ha'olam), i.e., so that their captors won’t oppress them too heavily and guard them too zealously.
Hilchos Matnos Aniyim 8:13
If a person sells himself and his children to non-Jews, or if he borrowed money from them and they held him captive or imprisoned him for defaulting on the loan, it is a mitzvah to redeem him twice, but not a third time. However, if the father passes away, we do redeem his children. If they want to kill him, then we redeem him even if this happens multiple times.