תהלים, פרק ק״ט, פסוק י״ד

A severe curse is directed toward a wicked individual, calling for past sins to remain forever present before God rather than being forgotten. The exact nature of these lingering sins is understood in two distinct ways.

One approach views this as an expression of intergenerational punishment [רד״ק, אבן עזרא, מצודת דוד]. In this view, the plea is for God to recall the wrongdoings of the wicked person's ancestors and hold the current generation accountable for them. The curse asks that the father's guilt be remembered and the mother's failures never be erased, ensuring that the son bears the weight and consequence of his parents' actions [רד״ק, מצודת דוד, ביאור שטיינזלץ].

In contrast to the idea of inherited guilt, a prominent tradition shifts the focus entirely. Instead of sins committed by the parents, this approach interprets the curse as referring to the terrible wrongs the son committed against his own parents and grandparents [רש״י, אלשיך, חומת אנך]. This perspective specifically identifies the wicked figure as Esau and his descendants, Amalek. The guilt of the fathers represents the direct harm Esau inflicted on his family line. According to this view, Esau's evil behavior caused his grandfather Abraham to die five years early, and his actions ultimately led to his father Isaac losing his eyesight.

Similarly, the sin involving the mother is understood as the damage Esau caused to Rebekah. Commentators note that even while in the womb, Esau caused her physical harm, which prevented her from eventually giving birth to all twelve tribes [רש״י, אלשיך, חומת אנך]. Furthermore, his wickedness brought her such deep shame that her death and burial had to be kept a secret from the public. Her family hid her passing so that onlookers would not curse the woman who brought such a destructive son into the world [רש״י].