Nearing the end of the campaign against Amalek, the prophet Samuel takes it upon himself to complete the task that King Saul left unfinished. Despite being an elderly, spiritual, and pious man, Samuel seeks to sanctify the name of God and exact justice upon the enemy of the nation [אברבנאל]. He orders the Amalekite king, Agag, to be brought before him. Samuel assumes the defeated king will have to be dragged against his will, but to his surprise, Agag steps forward on his own [אלשיך, ביאור שטיינזלץ].
The manner in which Agag approaches is understood in two distinct ways. The primary approach among commentators is that he is physically bound, brought forward in iron chains to prevent any chance of escape. In contrast, another group of commentators suggests he walks in a proud, pampered, and royal manner, perhaps even with a sense of joy and pleasure regarding what is about to unfold [רש״י, רד״ק, אברבנאל, מלבי״ם, צאינה וראינה, ביאור שטיינזלץ].
Upon meeting Samuel, Agag makes a declaration about the bitterness of death, reflecting a complex mental state. Some interpret his words as a realization that his end has arrived. Understanding immediately that Samuel intends to execute him, Agag declares that the bitter reality of death is finally upon him [רש״י, רד״ק, מצודת דוד, ביאור שטיינזלץ, צאינה וראינה].
However, many commentators understand Agag to mean the exact opposite, expressing that the bitterness of death has actually passed and departed from him. They offer several reasons for this sudden relief. Some suggest that upon seeing Samuel's pious and merciful appearance, Agag mistakenly believes this holy man will take pity on him and spare his life [רלב״ג, אברבנאל]. Others propose that Agag fully knows he is about to die but prefers execution over a lingering life of captivity, shame, and disgrace, making death a sweet comfort rather than a heavy burden [מלבי״ם, רד״ק, אברבנאל]. Additionally, the very fact that he is to be killed by a great leader and prophet, rather than a commoner, removes the humiliation of his execution [חומת אנך].
Another layer of interpretation connects Agag's sense of relief to the continuation of his family line. According to this tradition, Agag managed to father a child the previous night, an ancestor to the future wicked Haman. Comforted by the knowledge that his offspring will one day take revenge, the bitterness of dying childless leaves him [אלשיך, חומת אנך, אהבת יהונתן]. In response to Agag's feelings of victory and relief, Samuel ensures that the execution is carried out in a harsh and unusual manner. Acting measure for measure, Samuel's method of execution is specifically intended to symbolize the ultimate eradication of Agag's descendants and the complete destruction of his lingering hope [רלב״ג, אלשיך, חומת אנך].