Choosing Umar, Then Uthman, as Emissary to Quraysh

Shaykh Yasir Qadhi explains:

After the near-disaster of Khirāsh ibn Umayyah's mission, the Prophet ﷺ turned to a Companion of Qurashī blood, choosing ʿUmar ibn al-Khaṭṭāb, likely, Dr. Qadhi suggests, for his physical strength and well-known courage, since walking into Makkah as a free Muslim for the first time in six years required genuine bravery, fitting for the same man who had once publicly announced his own conversion by daring anyone who wished to see his mother weep for him to challenge him openly.

ʿUmar, however, offered the Prophet ﷺ a candid assessment rather than accepting immediately: his own history of open hostility toward Quraysh was well known, he told him, and he feared they would kill him outright, especially since his own clan of Banū ʿAdī no longer had the standing in Makkah to protect him, protection in Qurashī custom coming from tribal backing rather than personal strength alone. He offered to go regardless if commanded, but suggested that ʿUthmān ibn ʿAffān would carry greater standing in Quraysh's eyes.

Dr. Qadhi highlights a genealogical detail often overlooked: of the four men most closely associated with the early caliphate, ʿUthmān held by far the closest blood tie to the Makkan elite. Abū Bakr and ʿUmar were only distant cousins of Quraysh's leading families, several generations removed, while ʿUthmān descended from Banū ʿAbd Shams, the brother line to Banū Hāshim just three generations back, making him a close relative of Abū Sufyān, by then Makkah's undisputed leader. The Prophet ﷺ accepted ʿUmar's suggestion over his own initial choice and sent ʿUthmān ibn ʿAffān into Makkah in his place, an episode Dr. Qadhi cites, alongside the earlier shift from his own initial battle plan to Abū Bakr's counsel, as clear evidence that the Prophet ﷺ exercised genuine independent reasoning (ijtihād) in matters left open to his own judgment, readily adopting a better suggestion when one was offered.