Abu Sufyan's hopes of a swift and decisive victory over the Muslims lay in him.

Abu Sufyan's hopes of a swift and decisive victory over the Muslims lay in him. M. Shibli, the Indian historian, and Abbas Mahmood Al-Akkad, the Egyptian historian, say that Amr ibn Abd Wudd was reckoned, by the Arabs of the time, to be more than a match for one thousand cavaliers. Amr ibn Abd Wudd had no interest in the static warfare of a siege. He panted for action. When a few days had passed, and nothing had happened, he lost patience, and he decided to capture Medina by personal action.

One day, prowling around Medina, he and three other Makkan knights discovered a rocky point where the trench was not too wide. They spurred their horses from it, and succeeded in clearing the trench! Now Amr was inside the perimeter of Medina. He boldly advanced into the Muslim camp, and challenged the heroes of Islam to come out and fight against him in the classical Arabian tradition of duels. Amr's first challenge went unanswered whereupon he repeated it but still got no answer.

Such was the prestige of his name that no one in the Muslim camp dared to meet him in a trial of strength. If the idolaters saw in him their hope of victory, the Muslims saw in his challenge the sentence of their death. Amr ibn Abd Wudd threw his insolent challenge a third time and taunted the Muslims at the same time for their cowardice. To Amr it must have seemed that the Muslims were paralyzed with fear, which most of them, in fact, were.

Al-Qur’an al-Majid has also drawn a portrait of the state of the Muslims at the siege of Medina in the following verses: Behold! They came on you from above you and from below you, and behold, the eyes became dim and the hearts gaped to the throats, and you imagined various (vain) thoughts about God! (Chapter 33; verse 10) Behold! A party among them said: “you men of yathrib! You cannot stand (the attack).

Therefore go back” and a band of them asked for leave of the Prophet saying, “truly our houses are bare and exposed.” Though they were not exposed: they intended nothing but to run away. (Chapter 33; verse 13) Amr ibn Abd Wudd even expressed amazement that the Muslims were not showing any eagerness to enter paradise where he was ready to send them. It is true that most of the Muslims were terror-stricken but there was one among them who was not.

He had, in fact, volunteered to accept Amr's very first challenge but the Prophet had restrained him, hoping that someone else might like to face him (Amr).