The Journey to Syria
Signs of Prophethood Before the Revelation: The Story of Maysarah and the Two Monks
Before the revelation descended upon him, before the angel Jibreel appeared in the Cave of Hira, there were already signs—subtle, profound, unmistakable signs—that Muhammad ibn Abdullah ﷺ was destined for something extraordinary. This is the remarkable account of his trade journey to Syria with Maysarah, the servant of the noble Lady Khadijah bint Khuwaylid (may Allah be pleased with her).
It is a story filled with miracles, prophecies, and the unmistakable character of the one who would become the Seal of the Prophets.
Khadijah’s Commission
Maysarah, the trusted servant of Lady Khadijah bint Khuwaylid, set out with the Messenger of Allah ﷺ on a trade caravan to Syria. This was before the prophetic mission began, when Muhammad was still known simply as Al-Amin (the Trustworthy) and As-Sadiq (the Truthful).
Khadijah had instructed Maysarah to accompany Muhammad ibn Abdullah on his journey, to serve him, attend to his needs, and observe his conduct. She had heard of his honesty and trustworthiness, and wanted to test him in her business affairs.
The Noble Character Revealed
From the moment the caravan departed Makkah, Maysarah began to notice qualities in the Prophet ﷺ that amazed and impressed him. He was excellent in his dealings, noble in character, gentle in manner, truthful in speech, and far removed from disputes and arguments.
Maysarah carefully memorized everything he witnessed, intending to report it all to his mistress upon their return.
The Cloud and the Monk Nastura
As the caravan approached the land of Syria, they stopped to rest under the shade of a tree near the hermitage of a Christian monk named Nastura (also known as Nestor). This monk knew Maysarah well, as he was accustomed to seeing him every year with Khadijah’s trade caravans.
“O Maysarah, who is in this caravan?”
“Men from Quraysh, they change every year.”
“I looked at you from afar and saw a cloud shading the caravan, moving when you moved and stopping when you stopped. I have never seen anything like it before. Who among the caravan is of noble lineage?”
“He is Muhammad ibn Abdullah ibn Abdul-Muttalib, and he is trading for Khadijah this year.”
The shade that followed the Prophet ﷺ was not an ordinary cloud. It was a divine sign, a protection from the heat of the desert sun, moving with him and stopping when he stopped. Such signs were known from the scriptures to accompany the final prophet.
The Monk’s Questions
The monk asked permission to see him. When Maysarah agreed, Nastura approached and greeted the Messenger of Allah ﷺ, then began examining his face and features in prolonged silence. Then he turned aside to Maysarah and began asking specific questions:
“This redness in your companion’s eyes—is it something that happened during the journey?”
“No, it has been with him since birth.”
“Was he born an orphan?”
“Yes.”
“And what of his mother?”
“She died when he was six years old.”
“Does he swear by Al-Lat and Al-Uzza?”
“He abhors them and is not pleased to be asked to swear by them.”
The Declaration of Nastura
After hearing Maysarah’s answers, the monk made a stunning proclamation:
“Preserve what I tell you. By the Lord of the heavens and the earth, by the Lord of Moses and Jesus, we are awaiting a prophet who will seal the line of messengers. Moses and Jesus gave glad tidings of him, and this is your companion. We find his name among us as Ahmad.”
“What does Muhammad mean among you?”
“It means the one who is not blamed, but is always praised.”
“And this is the meaning of Ahmad among us.”
“And [mention] when Jesus, the son of Mary, said, ‘O children of Israel, indeed I am the messenger of Allah to you confirming what came before me of the Torah and bringing glad tidings of a messenger to come after me, whose name is Ahmad.'”
— Surah As-Saff (61:6)
This meaning—mentioned by the monk before the revelation—would later be confirmed in the Quran itself, proving that the scriptures of the People of the Book indeed contained prophecies about the final messenger.
Nastura’s Final Counsel
“O Maysarah, stay close in his service. If he ever announces that he is the Messenger of Allah, do not deny him. And beware—do not reveal what I have told you to anyone, for he will have enemies. Guard him well and do not let him be alone with any of them.”
Maysarah said: “I understood all of this and kept the matter secret within myself.”
The Second Monk’s Test
The caravan proceeded to the market, where the Prophet ﷺ sold Khadijah’s goods. He was excellent in his dealings and clear in his terms. Another monk, whose name was not mentioned, came and purchased some goods from him, then began to argue with him about the price.
“We did not agree on this price!”
As the discussion intensified, the monk said:
“Swear by Al-Lat and Al-Uzza that your word is correct.”
“I have never hated anything as much as I hate Al-Lat and Al-Uzza. Do not ask me to swear by them. Take your goods, and your word stands.”
The monk had not truly disputed the price—he was testing Muhammad ﷺ. He wanted to see how he would react when asked to swear by the idols. When the Prophet refused with such vehemence, the monk recognized the sign he was looking for.
The Second Monk’s Declaration
Seeing this response, the monk approached Maysarah privately:
“Who is this man?”
“Our master and the son of our master.”
“Guard your companion well, for he is the Seal of the Prophets. He is truthful. What I did was only to test him. I wanted to see if he would swear by Al-Lat and Al-Uzza, and when he refused, I knew he was the awaited prophet. I also saw the cloud shading him above all others in the caravan—and this only happens for a prophet.”
Maysarah said: “My certainty increased in what I had heard.”
Unprecedented Profit and Noble Refusal
The Messenger of Allah ﷺ sold the goods with tremendous profit—many times what people usually earned on such journeys. He then purchased goods from Syria suitable for sale in Makkah.
When they prepared to return, Maysarah made a suggestion:
“O Muhammad, why don’t you go ahead of the caravan to Makkah and give Khadijah the good news of the profit? Perhaps she will increase your payment.”
“I did not come out seeking to multiply my payment. We made an agreement and that is the end of it. I will not leave the caravan until I enter Makkah with it.”
Maysarah said: “This was a new quality I observed in him: contentment with wealth, fulfillment of agreements, and lack of greed for what had not been stipulated.”
Maysarah’s Report to Khadijah
When they returned to Makkah, Maysarah recounted to Lady Khadijah bint Khuwaylid (may Allah be pleased with her) everything he had witnessed of his character, everything he had heard from the words of the two monks, and the tremendous profit that had been achieved.
Her admiration for him increased, his status grew in her eyes, and this was among the reasons that paved the way for their blessed marriage thereafter.
This blessed journey reveals profound truths about the character of the Prophet ﷺ even before his prophethood was announced:
- Divine Signs: The miraculous cloud that shaded him, recognized by those who knew the scriptures
- Pure Monotheism: His innate hatred of idolatry, refusing even to swear by false gods
- Prophetic Characteristics: Orphanhood, lineage, and physical signs known from ancient prophecies
- Noble Character: Excellent dealings, fulfillment of agreements, contentment, and lack of greed
- Scriptural Prophecies: The People of the Book knew of his coming and could recognize him by the signs
- Divine Preparation: Allah was preparing hearts to recognize His final messenger
Upon him be the best of prayers and peace
Sirat Ibn Hisham
Edited by: Taha Abdul-Rauf Saad
Author: Hatim Hegab
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