Ka'b Ibn Al-Ashraf

Ka'b ibn al-Ashraf (Arabic: كعب بن الاشرف‎) (died 624) was a poet from the Tayy tribe who criticized and mocked the Islamic prophet Muhammad. Ka'b ibn al-Ashraf was born to a Jewish-Arab mother from the Nadir tribe, Aqilah bint Abi'l-Huqayq, and an Arab father from the Tayy tribe, and he followed his mother's religion. He was a wealthy man known for his handsomeness, and a poet living in luxury in his fort south east of Medina at the rear of Banu Nadir’s habitations.

According to several ahadith in Sahih al-Bukhari, he wrote poems satirizing Muhammad, eulogizing Quraish and enticing them against the Muslims. He then rode to Mecca where he started to trigger the fire of war and kindle rancour against the Muslims in Medina. When Abu Sufyan asked him which religion he was more inclined to, the religion of the Meccans or that of Muhammad and his companions, he replied that the pagans were better guided.

Read more about Ka'b Ibn Al-Ashraf:  Interactions With Muhammad