The genealogy of Simeon’s descendants contains a striking anomaly not found among his brothers. While the other sons of Jacob are listed alongside their children without any mention of their wives' origins, Simeon's youngest son is explicitly identified as the child of a Canaanite woman. The primary approach among commentators is that this detail highlights a significant deviation from the family tradition. Jacob’s sons were careful to uphold the directives of Abraham and Isaac to avoid marrying Canaanite women, choosing instead to marry women of Aramean, Egyptian, Edomite, or Midianite descent. Simeon, however, acted improperly by marrying a Canaanite, and this detail is recorded as a mark of criticism [אבן עזרא, חזקוני, תולדות יצחק, ביאור שטיינזלץ, נתינה לגר]. Some clarify that Simeon initially adhered to the family tradition, but after his first wife bore him sons, he took a second wife from Canaan, who gave birth to his youngest [רד"ק, מחוקקי יהודה].
A vast Midrashic tradition offers a completely different understanding, suggesting that the description points to a specific, well-known woman rather than an ordinary merchant. According to this tradition, the "Canaanite" woman is actually Jacob’s daughter, Dinah, who was given this title after being violated by Shechem the Canaanite. Following the destruction of the city by Simeon and Levi, Dinah was overcome with shame and refused to leave Shechem's house, fearing that no one would ever marry her. To rescue her, Simeon swore that he would take her as his wife, and from this union, his youngest son was born [רש"י, רד"ק, טור, צאינה וראינה].
This interpretation raises a severe legal and moral difficulty: how could Simeon marry his own sister? Commentators offer several resolutions. Some explain that before the Torah was given, the Patriarchs observed the commandments by choice and held the legal status of converts, or they acted upon divine inspiration to establish the tribes of Israel. Additionally, under ancient Noahide law, marrying a maternal sister was not strictly forbidden [מזרחי, ריב"א, גור אריה, פרדס יוסף, ברכת אשר, שפתי חכמים]. A more mystical explanation draws on a tradition that Dinah's gestation primarily occurred in the womb of Rachel. Therefore, on a fundamental level, she was not considered the full sister of Simeon, who was the son of Leah [טור, פענח רזא, משכיל לדוד]. Another unique approach resolves the issue by slightly adjusting the tradition, suggesting that Simeon did not swear to marry Dinah himself, but rather promised to find her a match and marry her off to one of his sons [ברטנורא].
The identity of this youngest son also draws significant attention. One perspective proposes that he was not Simeon’s biological child at all, but rather the son of Dinah and Shechem. Because a child’s status follows the mother, he was adopted into Simeon’s household, despite physically being the son of the Canaanite [רש"ר הירש]. Another tradition connects this son to a much later event, identifying him as Zimri, the prince of the tribe of Simeon who tragically sinned with a Midianite woman. According to this view, the roots of Zimri's moral corruption were already planted here, stemming from his complex origins as the son of the Canaanite woman [הכתב והקבלה, מחוקקי יהודה].