In early autumn, a fateful encounter takes place that will ultimately seal the destiny of the remaining survivors in the land of Israel. A high-ranking figure arrives with his entourage to meet the governor appointed by the Babylonians. He is welcomed warmly to a shared meal, an event that ends in a tragic betrayal.
The encounter occurs in the seventh month, known as Tishrei. The primary approach among commentators is that this meeting actually took place on the holiday of Rosh Hashanah. Because it is a festival day, the Fast of Gedaliah was established for the day immediately following the holiday [רד״ק, ביאור שטיינזלץ, אברבנאל].
The assassin, Ishmael, arrives at the city of Mizpah from the neighboring land of Ammon [מצודת דוד, חומת אנך, אברבנאל]. His arrival is driven by a complex mix of personal and political motives. On a personal level, his actions are fueled by deep jealousy. Ishmael comes from royal lineage, belonging to the family of King David and King Zedekiah. Because of his royal blood, he firmly believes that the right to rule the land belongs to him, and he deeply resents Gedaliah for holding the governor's position [רוב המפרשים]. There is a tragic symbolism in his heritage: just as his relative King Zedekiah led to the destruction of Jerusalem, Ishmael brings about the final disaster by assassinating Gedaliah [חומת אנך].
Furthermore, Ishmael is recognized as one of the king's senior officers who had managed to escape exile to Babylon [רש״י, רד״ק, ביאור שטיינזלץ]. His dual status as both a royal descendant and a prominent commander only intensifies his sense of entitlement and deprivation [מצודת דוד]. Adding a historical layer to his background, ancient traditions trace Ishmael's roots back twenty-four generations to a royal convert who joined the Jewish people [רד״ק].
Beyond his personal grievances, Ishmael is driven by a broader political agenda. He operates as an agent sent by the king of Ammon. The Ammonite ruler harbors a deep hatred for the king of Babylon and seeks to undermine Babylonian authority in Judah. By choosing a Jewish insider like Ishmael for the task, the king of Ammon ensures that the assassin can use deception to get close to Gedaliah, murder him, and ultimately transfer control of the region into Ammonite hands [מלבי״ם, חומת אנך, אברבנאל].
The encounter reaches its climax as the men sit down to eat together. They partake in a meal of bread, a standard term for a full feast [מצודת ציון]. This shared meal sharply highlights the tragedy of the moment. Gedaliah receives his guests with open arms and genuine hospitality, completely ignoring all the prior warnings he had been given regarding Ishmael's malicious intentions [ביאור שטיינזלץ].