There is a kind of man the world produces in every age: too clever to be cornered, too charming to be refused, the one sent into the room when an impossible thing has to be talked into happening. Quraysh prized such a man, and called him Dahiyat al-Arab, the most cunning of the Arabs, the one against whom other men measured their own intelligence. For years he turned all of that gift against the Prophet Muhammad ﷺ, hunting the believers across seas and into foreign courts. And then, in the late afternoon of his life, the same cunning was placed in the service of the One who had made it. The story of Amr ibn al-As (may Allah be pleased with him) is the story of what happens when a brilliant man is finally outmatched, and is grateful to lose.
The oldest of the young
Imam al-Dhahabi gathered the praises the Arabs heaped on him: the most cunning of Quraysh, a man of the world, an elegant poet, a horseman and warrior counted among the bravest of his people. He combined nearly everything the Arabs admired in one person, and he knew it. He was older than Umar ibn al-Khattab and used to say he remembered the very night Umar was born. That detail places him precisely. He was not one of the white-haired elders like Abu Jahl who took the Prophet ﷺ as an enemy from the first day, nor one of the youths like Khalid who came later to avenge a fallen father. He stood between the fathers and the sons, the oldest of the young and the youngest of the old, and he fought the Prophet ﷺ at both Badr and Uhud, which few of his generation did.
Allah was preparing him long before he knew it. Amr was the most traveled merchant of Quraysh: Syria and Palestine and Jordan, Egypt, the land that is now Libya, Abyssinia, Yemen. He knew the roads and the fortresses and the cities of those lands, and had built relationships with their rulers, Roman and Persian alike, in the easy manner of a trader welcome everywhere. Decades later, when he returned not as a merchant but as a general, he already knew the terrain by heart. A childhood spent counting profit was, without his knowing it, a map being drawn for a future he could not yet imagine.
His enmity to the Prophet ﷺ ran deeper than Khalid's. Khalid was a soldier: call him to the battle and he would win it. Amr was a schemer. He plotted, intercepted, and persecuted, in lockstep with his father al-As, whose verses fill the Qur'an as one of the bitterest opponents of the message. When al-As died, undone by the supplication the Prophet ﷺ had made against him, Amr inherited all his wealth, for his only full brother, Hisham, was in prison for the crime of being a Muslim, and would remain in torment for ten years. So Amr carried it all into his fight, and aimed every bit of it at the believers.
The court of the Negus
His cunning has no better stage than Abyssinia. The Prophet ﷺ had sent a band of the most persecuted believers across the sea to seek refuge with the Negus, a Christian king who would not tolerate injustice. Among them were Ja'far ibn Abi Talib, Uthman ibn Affan and the Prophet's daughter Ruqayyah, Umm Salamah, Az-Zubayr; among them too were Amr's own brother Hisham and a half-brother through his mother. His own kin had fled to escape men like him, and that, somehow, only sharpened his hunger to drag them back.
Quraysh chose him for the extradition, and he came with a strategy. The night before his audience he went from one of the king's confidants to the next with the finest leathers of Arabia, buying their voices in advance. His plan was clean: keep theology out of it. He would simply tell the king these were troublemakers, on neither your religion nor mine, a suspicious people who would sow discord in your land; send them home and we will deal with them. It was anti-refugee talk pitched perfectly to a king's fear of disorder, and Amr delivered it better than any man alive.
The Negus refused to be hurried. "What kind of a man would I be," he said, "if I do not hear their case?" He called the believers. Ja'far rose and gave one of the most beautiful descriptions of Islam ever spoken: that they had been a people of ignorance who worshipped idols, ate carrion, and let the strong devour the weak, until God sent from among them a man of known truthfulness, who commanded them to speak the truth, keep their promises, honor their kin and neighbors, and refrain from bloodshed. The king looked at Amr and said he saw nothing in these people that would let him hand them over, and that whoever harmed them would answer to him.
Amr would not take the loss. His own companion told him to go home, that these were after all their own families and the obsession had become unseemly. Amr answered that he would not leave Abyssinia without all of them in chains. He had found the crack. "They said nothing about Jesus," he told his friend. He would return and say these people blaspheme about the Messiah, that they call him a mere creature and deny he is the son of God. The king summoned them once more and asked Ja'far what he said about Jesus, son of Mary. Ja'far answered that they said only what God had revealed, and recited the verses of Surah Maryam. The king wept, and his bishops wept until their beards were wet, recognizing the truth in the words. This was the moment the believers later linked to a verse of Surah al-Ma'idah, about the Christians whose hearts soften when they hear the revelation:
and when they listen to what has been sent down to the Messenger, you will see their eyes overflowing with tears because they recognize the Truth [in it]. They say, 'Our Lord, we believe, so count us amongst the witnesses.'
Qur'an 5:83
The king took a stick and drew a line on the ground. By God, he said, Jesus does not exceed what you have said by the length of this twig. The bribed generals grunted; even if you grunt, the king told them, these people are protected, and whoever harms them will answer to me. Then he turned to Amr and dismissed him. Amr had failed for the first time in his life. He sailed home empty-handed, and the people of Mecca whispered that if even Amr could not bring them back, then surely this Muhammad ﷺ truly received revelation, for no one had ever slipped through his hands. He poured his rage upon his brother Hisham and the captured believers, fought at Badr, commanded a flank at Uhud, and helped architect the great army that came to wipe out Madinah at the trench of Khandaq and was turned back by the wind and the will of Allah.
The verse that answered a prayer
Somewhere in those years the Prophet ﷺ raised his hands and supplicated against Amr. Such prayers had undone other men. But here Allah answered His Prophet not with a punishment but with a revelation, gently lifting Amr's fate out of human hands:
Whether God relents towards them or punishes them is not for you [Prophet] to decide: they are wrongdoers.
Qur'an 3:128
It was not yet Amr's time, and it was not the Prophet's decision to make. There was a plan for this difficult man. And his brother Hisham, tortured into renouncing his faith and sure he had ruined himself forever, was among those for whom the verse came down telling the despairing servant never to lose hope in the mercy of Allah. Two brothers, two doors held open when both looked, from the outside, firmly shut.
The change came after Khandaq. Amr saw the way the wind was blowing, gathered a few trusted friends from Quraysh, and said plainly that Muhammad ﷺ seemed to be winning. His plan had a strange poetry to it: let them go to the Negus and become the refugees this time, as the Muslims once had. If Quraysh prevailed, they could slip back to Mecca and pretend none of it had happened; but if Muhammad ﷺ prevailed, to live under the Negus was far better than to face what the Prophet ﷺ might do to men like them. So they loaded the finest gifts and sailed.
In the palace Amr saw a man he recognized: Amr ibn Umayyah, the Prophet's own envoy. His old arrogance flared, and he pressed the king for permission to kill the messenger then and there. The Negus struck him so hard across the face that he nearly broke his nose. Wake up, the blow said. Amr wished the earth would swallow him. And then the king spoke the words that broke him open: you ask me to hand over the envoy of the man to whom comes the very angel that used to come to Moses.
That language was a key turning in a lock. Years earlier Waraqah ibn Nawfal had used the same words to the Prophet ﷺ after the first revelation: this is the Namus, the one who came to Moses. The Negus read the same scriptures and reached for the same phrase, and faith struck Amr in that instant. He had watched the Prophet ﷺ for years and felt nothing; now this learned king swore sincere counsel: go back and follow him, for Allah will give him victory as He gave Moses victory over Pharaoh. Then take my pledge to Islam on his behalf, Amr said. And so the Negus, who never met the Prophet ﷺ, became the only man of the second generation in history to receive the pledge of Islam from a future companion. He extended his hand, and Amr took it.
The last of the emigrants
He slipped away from his sleeping companions in the night and rode for Madinah. In the desert he met two riders, Khalid ibn al-Walid and Uthman ibn Talha, also on their way to surrender to the Prophet ﷺ. Where are you going, Abu Sulayman, Amr asked. To become Muslim, Khalid answered; this man is a prophet, I no longer have any doubt. Then by God, said Amr, so am I. The sons of the men who had fought the Prophet ﷺ hardest were riding to lay down their swords. They reached Madinah, and the Prophet ﷺ received them with open joy, knowing they came this time not to strike him but to embrace him.
When his turn came to give the pledge, Amr the diplomat pulled his hand back. He would take it, he said, on the condition that all his past sins be forgiven; and, with rare honesty, would not ask the same for whatever sins lay ahead. The Prophet ﷺ did not grant him a personal exception. He told him something better: do you not know that Islam erases all that came before it, and the migration erases all before it, and an accepted Hajj erases all before it? It was already in the contract. Amr did not need a favor; he needed only to enter the door that mercy had already opened. Remember his fear of the sins still to come. It will return at the very end of his life.
Doubts could be raised: did he believe, or was he merely a clever man reading the odds? The Prophet ﷺ settled it himself. The two sons of al-As, he said, are two believers, and Amr a man rightly guided in his affairs. And in the most beautiful testimony of all: the people became Muslim, but Amr ibn al-As truly believed. When an alarm once sounded at the edge of the city and Amr, with Salim the freedman of Abu Hudhayfah, rushed out to defend it, the Prophet ﷺ asked, would you not do as these two believers have done? The hardest heart in Quraysh had become one of the first to run toward danger for the sake of Allah.
His proving came fast, at a small expedition called Dhat al-Salasil, where the Prophet ﷺ sent him as a commander and said Allah would grant him victory and spoils. Amr bristled at the word. By God, he said, I did not become Muslim for wealth, but out of desire for Islam and to be with the Messenger of Allah ﷺ. How excellent, the Prophet ﷺ answered, is honest wealth in the hand of a righteous man. That a man might fear wealth would stain his sincerity was itself the measure of how far his heart had traveled.
Consider, too, what the Prophet ﷺ entrusted to him only weeks into Islam: command of three hundred, among them Abu Bakr and Umar, and even the seasoned Abu Ubaydah ibn al-Jarrah submitted to him for the sake of unity. On a freezing night, fearing he would die if he bathed in the cold, Amr led the prayer without a full washing, and when questioned recited the words of Allah:
Do not kill each other, for God is merciful to you.
Qur'an 4:29
The Prophet ﷺ laughed and let it pass. Amr was being grown, and the men around him, into something larger than their pride.
A heart learning to love
What is most moving about this period is not the conquests but the softening. Amr, the man who once schemed against the Prophet ﷺ, now could barely raise his eyes to him. I was so shy before the Messenger of Allah ﷺ out of awe and love, he said, that I never filled my eyes with looking at him. The cunning had not vanished, but it was being purified, turned outward into generosity. On a journey the Prophet ﷺ said three times, may Allah have mercy on Amr; and when asked why, he explained that whenever he called the people to give in charity, Amr would come and give all that he had, and when asked where it came from, would answer, from Allah. The man who had inherited a fortune from an enemy of God was now emptying it into the cause of God and crediting none of it to himself. The Prophet ﷺ trusted him as governor of Oman, where many embraced Islam under him, for the believers compelled no one; there is no compulsion in religion. He stayed there until the Prophet ﷺ passed from this world.
From Rafah to Egypt
After the Prophet ﷺ, under Umar, Amr came fully into his own. It was not fitting, Umar said, for Amr ibn al-As to walk the earth except as a leader. While Khalid drove into the Persian empire, Amr drove into the Roman; most of southern Palestine fell to him, all the land below Jerusalem, secured so that Umar himself could come and take the keys of the holy city in peace. There he met his match in cunning, Artabun, the cleverest of the Romans, and outwitted him too.
Then he set his eyes on Egypt. Umar was wary: the Romans and Persians were enough; leave Egypt alone. Amr answered that he had four thousand men against a hundred and twenty thousand, but that he had a plan, and he understood its people: the Coptic Christians of Egypt, despised by their Byzantine rulers and resentful of them. And so this companion stationed himself at the very edge of the two worlds, in Gaza, and in Rafah; the letters between him and Umar passed from Rafah to Madinah. On that ground that aches in our hearts today, the companions camped and negotiated. Amr told the Egyptians that the Prophet ﷺ had foretold that Allah would one day open Egypt to them, and had commanded that they be treated with kindness, for they were kin through Hajar, the mother of Ismail.
He received Umar's letter to halt only after he had crossed into Egypt, as he had arranged, so that he might say truthfully it had reached him too late. With his four thousand he took Alexandria, and the Byzantines fled. Many Egyptians embraced Islam, drawn by a justice the histories record with wonder, so unlike the rule they had known. Where his army's tents had stood, Amr built the city of Fustat, the city of tents, which the centuries would absorb into what we now call old Cairo. Companions filled its neighborhoods, and raised there a mosque that still bears his name. A man who had spent his youth fighting the believers ended it building a city where the believers prayed.
What Amr's life asks of our faith
Amr ibn al-As died past the age of ninety, and the most important thing he ever did, he did on that deathbed. His son Abdullah sat beside him, and Amr divided his life into three parts. In the first, he said, I fought the Prophet ﷺ, and had I died then I would surely have been among the people of the Fire. In the second I embraced Islam and was at his side, and had I died then I would have been certain of Paradise. But this last part, the years of politics and trial and the mistakes I made, of this I know nothing. His son reminded him how the Prophet ﷺ had loved him, but Amr would not lean on it: perhaps, he said, the Prophet ﷺ only drew me close to soften my hard heart. Then he raised his finger to the sky and repeated, there is no god but Allah, there is no god but Allah, until the words carried him out of this world.
Here is what his life asks of you. It asks you to believe that no past is too far gone for Allah's mercy to reach. This was the most cunning enemy the Prophet ﷺ had, who fought at Badr and Uhud and built the army of Khandaq, and the Prophet ﷺ told him to his face: Islam erases all that came before it. If you carry a history that whispers you are beyond forgiveness, Amr is the standing refutation of that whisper. The door that mercy held open for him has not closed.
It asks you about your sincerity. Wounded that anyone might suppose he had come for wealth, Amr said he had become Muslim not for money but out of desire for Islam and to be near the Messenger of Allah ﷺ; then, called to give in charity, he gave everything and named no source but Allah. Ask yourself, plainly, what you are for. Is your worship for Allah, or for the way it makes you appear? Could you, like Amr, give away what you cherish and say only, it is from Allah, wanting nothing back from the people who watched you give it?
And it asks you to hold, at once, both hope and fear of Him. Amr did not die boasting of his conquests. He died trembling, dividing his life honestly, clinging with his last breath to la ilaha illa Allah. That is the balance the believer is meant to walk: to hope in Allah's mercy without growing careless, and to fear His justice without despairing. A man who had conquered Egypt feared for his soul. How then should we, who have conquered nothing, carry ourselves before our Lord, except in humility, returning to Him with that same word on our tongues?
So take something small and real from him into this very day. Give one thing in charity that no one will trace back to you, and answer in your own heart, it is from Allah. Make tawbah for the part of your life you are least proud of, and believe it is accepted, because Islam erases what came before it. And keep close the last word he reached for, repeating la ilaha illa Allah until it is the most familiar thing on your tongue, so that whenever your own final moment comes, your finger too is pointing at the sky. May Allah be pleased with Amr ibn al-As, forgive him the years he himself was unsure of, and grant us a return to Him as sincere, and an ending as certain, as the one he prayed for.
This chapter follows the account of Amr ibn al-As (RA) in Dr. Omar Suleiman's series The Firsts (Yaqeen Institute). Qur'an translations are from M.A.S. Abdel Haleem (5:83, 3:128, 4:29). Where the histories carry more than one narration, the most widely reported has been followed.