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It was on Rosh Hashana, at the festive meal, that Yishmael the son of Netanya and ten accomplices went to Gedaliah in Mitzpah. They assassinated Gedaliah, as well as the Chaldean officers who were on the premises. Two days later, before the news had been well-publicized, eighty men came from Shechem, Shiloh and Samaria, mourning over the destruction of the Temple. (They were still carrying the flour they intended to offer; the Temple had been destroyed while they were en route.) Yishmael the son of Netanya met them on the road, pretending to be in mourning like them, and invited them to detour to see Gedaliah (whom he had already killed). When he had escorted them into the city, he and his followers killed the travelers; they were keeping a lid on the assassination and preventing word from getting out. Ten men managed to avoid being killed by bribing Yishmael with the grain, oil and honey that they had stored in the fields.
Yishmael took the men he had killed and tossed them into a pit. The pit had been made by King Asa of Judah during his war with Baasa, king of Israel (see I Kings 15). Yishmael captured the people of Mitzpah, killing the men, and enslaving the women and children. Yishmael started to head for Amon, but Yochanan and the other officers found out about what he had done. They took their soldiers and marched on Yishmael's forces. When Yishmael's captives saw the army coming, they rejoiced and returned with Yochanan. Yishmael and eight of his men escaped and ran to Amon for refuge. Yochanan took the refugees to a place called Geirus Chimham, near Bethlehem, because it was on the way to Egypt. They were afraid that Chaldeans would blame everyone for Gedaliah's assassination.
Author: Rabbi Jack Abramowitz