A tragic generational shift occurs when a righteous man fathers a wicked son who completely rejects his moral legacy. This violent heir shatters the boundaries of truth, justice, and morality, choosing a life of corruption instead [מצודת ציון, רד״ק, ביאור שטיינזלץ].
The exact nature of the son's actions is a subject of deep discussion, particularly regarding how his behavior relates to a brother. The most direct understanding is that the son targets his own family. In this view, he commits severe crimes, such as robbery, directly against his brother [רש״י, מצודת דוד, רד״ק]. Alternatively, the idea of a brother serves as a moral contrast. Even if this wicked individual has a righteous sibling who upholds their father’s good deeds, the corrupt son refuses to learn from their example, consciously choosing a life of sin [מלבי״ם].
Another approach suggests that the description does not refer to a family member at all, but rather uses a shortened expression to indicate that the son commits at least one offense from a broader list of grave sins [רד״ק]. Finally, a more emotional perspective views the phrasing not as a literal sibling or a number, but as a visceral cry of pain. It represents an exclamation of deep sorrow over the tragedy of a son deliberately committing the exact evil acts that his righteous father so carefully avoided [ביאור שטיינזלץ].