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The road to Gehinnom is paved with good intentions – such as the unwarranted benefit of the doubt that too-credulous well-intended leaders and negotiators give their undeserving counterparts.

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Doubts make men wise. Midrash Shmuel, on Avot 1:11.

Although the Ishmael who was the son of Abraham and Hagar was the most famous person who bore this name (followed perhaps by the narrator of Moby-Dick), and although many of his descendants are responsible for untold murders of Jews over the ages, it was a different Ishmael who personally affected the lives of all observant Jews directly for millennia, to this day, and continuing, for it was Ishmael ben Netaniah who assassinated Gedaliah ben Achikom (Kings II: 25: 25; Jeremiah 41:2) and “all the Jews who were with him” (Ibid Kings II; Jeremiah 41:3) in a murderous rampage that is commemorated throughout the world and the ages as the basis for Tzom Gedaliah, the Fast of Gedaliah, that takes place the day after Rosh Hashana every year. Two days after the assassination, Ishmael murdered another group of Jews and threw them into a pit (Jeremiah 41: 4, 7).

Curiously, the Book of Jeremiah says that Ishmael killed this second group of Jews “b’yad Gedaliah,” which has been translated as “because of Gedaliah” (Jeremiah 41: 9) or “by the side of Gedaliah” or “in the wake of Gedaliah’s [murder].”

The Gemara in the daf yomi recently studied around the world (Shevuot 20) refers to the Fast of Gedaliah, though almost incidentally, but the Gemara in Niddah (61) discusses the assassination of Gedaliah – and the murders of the people who were with him – in more detail, asking “Did Gedaliah kill [this second group of Jews, who were then thrown into a pit (Jeremiah 41: 4, 7)]? But didn’t Ishmael kill them?”

The Gemara answers: Rather, since [Gedaliah] should have been concerned based on the advice of Yochanan, son of Kareah, the verse blames Gedaliah as though he had personally killed this second group of Jewish men. This can’t be more fully understood without a reading of the relevant passages of the book of Jeremiah. (The version in the Book of Kings II is less detailed.)

The book of Jeremiah recounts that Yochanan, and “all the captains” that were with him, in effect warned Gedaliah (“asked ‘don’t you know?’”) that the king of Amon has sent Ishmael to kill him (Gedaliah) (Jeremiah 40: 13, 14).

And in an amazing act of heroism, Yochanan secretly offered Gedaliah to preemptively and secretly kill Ishmael to prevent him from killing Gedaliah and thereby to prevent all of Gedaliah’s followers from being scattered – “the remnants of Judah” (Jeremiah 40: 15). (Ironically, this is probably one of the most now-public examples of a “secretly” suggested plan to do something secretly – which was not carried out – in recorded history.)

But Gedaliah told Yochanan not to do this, “for you speak falsely of Ishmael” (Jeremiah 40:16). Perhaps the key takeaway is what was left unsaid, Gedaliah didn’t take any precautions to ascertain whether the rumors or allegations were true and to protect himself in case the reports about Ishmael’s intention may have been correct, as they turned out to be.

Rava then articulated the lesson that should be learned from this chain of events. Regarding the prohibition against listening to malicious speech (of particular relevance to our introspection and self-examination at the time of Rosh Hashana, the day before Tzom Gedaliah, and throughout the 10 Days of Penitence), one is still required to be “concerned,” and presumably to ascertain whether it is grounded in the truth. There is a famous proverb, “Hevay dan et kol ha’adam l’kaf zchut” (Pirkei Avot 1:6). One should give everyone the benefit of the doubt. Note that this extends to all people, not just Jews. Nevertheless, there is also a famous expression (told to and often repeated to me by my late father, OBM), Kabdayhu v’chashdayhu (Kallah Rabbati 9), literally, “honor and suspect,” or “honor respectfully, but simultaneously be on guard,” or, in the words of President Ronald Reagan, “Trust, but verify.”

The negotiations that are going on now with Hamas and with the Iranians are based in part on trusting those who have been proven untrustworthy in the past, to put it mildly. We – and, more importantly, the negotiators representing Israel – should learn the lesson of Gedaliah, ASAP, without waiting for the day after Rosh Hashana next year, or without waiting until the last Gemara in the daf yomi cycle, which is Niddah (cited above), where this discussion takes place. We were warned. We have options for pre-emptive actions, as offered by Yochanan to Gedaliah. We have knowledge of the Six-Day War, which was far faster, better, and less lethal than today’s wars in Gaza and the Ukraine. We have to consider that people who do not take adequate precautions and actions can be blamed for mass deaths that follow as was Gedaliah, to an extent, a hero whose place in history was so tragically truncated because of his failure to make adequate assessments which could have led to his taking adequate precautions, let alone preemptive actions.


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Rabbi Aaron I. Reichel, Esq., is a New York attorney who has written many articles on secular and Jewish topics, and has written, edited, and/or supplemented various biographies, most notably of Rabbi Herbert S. Goldstein ("The Maverick Rabbi"), Harry Fischel, and Chief Rabbi Shear Yashuv Cohen.