Aleppo, one of the oldest continuously inhabited cities in the world, holds significant geopolitical and economic importance due to its strategic location at the crossroads of major trade routes connecting Asia, Europe, and Africa. Historically, it served as a vital hub along the Silk Road, facilitating the exchange of goods, cultures, and ideas. Its fortifications and proximity to key regions like the Mediterranean, Mesopotamia, and Anatolia made it a crucial military and political stronghold. Its enduring influence underscores its role as a bridge between East and West, shaping regional power dynamics and global trade networks for centuries.
Aleppo’s Leadership
Abu ‘Ubaydah ibn al-Jarra (RH), commanding 17,000 troops, secured a treaty with Qinsarin and al-‘Awaṣim, accepting tribute in gold, silver, brocade, figs, and olive oil. News of the Muslim advance unsettled Aleppo’s residents, ruled by two brothers: Yuqanna, a war-driven king, and Yuhanna, a peace-seeking monk. Yuhanna urged surrender, but Yuqanna dismissed his counsel, vowing to defend Aleppo with 12,000 armored troops and additional forces. Determined to resist, Yuqanna fortified his position while Abu ‘Ubaydah, unaware of the impending threat, dispatched Ka’b bin Damrah with 1,000 reconnaissance troops to scout the city.
Yuqanna’s spies detected the Muslim presence, prompting an ambush that trapped Ka’b’s forces. Initially confident, the Muslims suffered heavy losses, including key warriors, but fought fiercely. Meanwhile, Aleppo’s leaders, disillusioned with Yuqanna’s defiance and fearing Muslim retaliation, sought peace independently. They sent a delegation to Abu ‘Ubaydah, offering surrender and assistance in governance. Although concerned for Ka’b’s fate, Abu ‘Ubaydah engaged with them, as they argued that peace would prevent depopulation and resistance, ensuring stability under Muslim rule.
Heroic Resistance Amid Devastating Losses
Yuqanna, aware of the approaching Muslim cavalry, set an ambush. Yuqanna led 5,000 troops to confront Ka’b’s forces, concealing additional soldiers nearby. As the Muslims performed ablution, they spotted Yuqanna’s army and, though outnumbered, charged with confidence. However, the hidden troops attacked from behind, surrounding and overwhelming the Muslims. Despite being trapped, the Kindah warriors displayed remarkable bravery, with 100 martyred in a single spot. Among the fallen were 170 senior fighters, including notable figures like ‘Abbad bin Asim an-Nakha’i, Zufar bin Umm Radi, Hazim bin Shihab al Muqri, Sahl bin Ashyam, Rifa’ah bin Muhsan and Ghanim bin Bard who was amongst those who had participated in the Expedition of Tabuk with Rasulullah and al-Yamamah with Khalid bin al-Walid. Despite heavy losses, the Muslims fought fiercely, each killing several enemies before falling. Witnessing this resilience, Yuqanna urged his men to stay, likening the Muslims to relentless wolves. Grieving his fallen comrades, Ka’b, clad in double armor, prepared for a final stand, calling on his horse, Hital, for one last battle. Despite waiting for reinforcements from Abu ‘Ubaydah, none arrived, leaving Ka’b and his men to face their fate alone.
The Aleppan Delegation and their Surrender
Abu ‘Ubaydah halted his march towards Ka’b, as a delegation of thirty Aleppan chiefs, who considered Yuqanna as tyrant approached seeking to surrender. They feared Yuqanna’s refusal to submit would bring destruction. The Aleppan leaders proposed surrendering the city to avoid bloodshed, regardless of Yuqanna’s fate. Abu ‘Ubaydah initially rejected their surrender despite their pleas, fearing deceit and the fate of Ka’b’s reconnaissance force.
As the Aleppans persisted, they warned that refusal would depopulate the region, leaving the land barren. Their emotional plea moved Abu ‘Ubaydah to tears, prompting him to reflect deeply on the situation. Abu ‘Ubaydah negotiated the terms of Aleppo’s surrender, initially demanding half the tribute Qinsarin provided. He set strict conditions: Aleppans would supply food, trade openly with the Muslim camp, and report enemy movements. Crucially, they were to prevent Yuqanna from seeking refuge in the city. The Aleppans agreed to all but barring Yuqanna, citing their inability to overpower him. Abu ‘Ubaydah accepted their limitations but required solemn oaths to uphold the other terms. He warned that any breach would void the treaty, leading to severe reprisals. The pact covered all inhabitants and introduced the annual Jizyah tax from the following year.
Yuqanna’s spies found out the Aleppans surrender and informed him when they were resting that night while fighting K`ab. Upon hearing this, Yuqanna grew fearful of losing his fort and immediately abandoned any plans to fight the remaining Muslims, despite having already killing over 200. Meanwhile Abu Ubaydah along with Kalid ibn Walid marched towards Aleppo to support K’ab and met them when Yaqunna and his forces had already left their camp.
Yuqanna’s Massacre and Aleppo’s Desperation
Yuqanna returned to Aleppo enraged upon learning of the treaty with the Muslims. Furious, he threatened to massacre the population, accusing them of betraying their faith by surrendering. When the Aleppans refused to revoke the treaty, he ordered his slaves to kill the treaty initiators, resulting in over 300 deaths. Yuhanna, Yuqanna’s brother, tried to intervene, arguing that Christ forbade such actions. When Yuqanna attempted to kill him, Yuhanna declared his conversion to Islam, proclaiming the Oneness of Allah and Muhammad as His Messenger before Yuqanna killed him.
As Yuqanna continued the slaughter, the Muslims, led by Khalid, arrived and launched a counterattack, killing over 3,000 enemy soldiers. Yuqanna fled to the fort, leaving his forces devastated. The Aleppans captured 40 of Yuqanna’s generals, offering them to Abu ‘Ubaydah. The Aleppans reported Yuqanna’s impregnable fort and Yuhanna’s martyrdom. Abu ‘Ubaydah prayed over Yuhanna’s body, buried him, and promised the Aleppans protection and a share of the future spoils.
The Attack on Aleppo’s Fort
The Muslims launched a fierce assault on the fort, and the enemy had the upper hand as it was on the hilltop. In the first attack, warriors from various tribes advanced courageously but faced heavy resistance from the enemy, who used catapults, and other weaponry. The attack was chaotic, with many Muslim soldiers retreating in fear as rocks struck and killed several of them. The siege resulted in the deaths of key Muslim fighters, and many others were wounded or crippled in the battle. Meanwhile, Yuqanna, witnessing the Muslims’ temporary defeat, expressed confidence that they would not return to the fort. He planned to use trickery to further weaken the besieging forces.
The Night Raid: Yuqanna’s Ambush
Yuqanna, determined to disrupt the Muslims’ camp, selected 2,000 elite soldiers and ordered them to attack at night, once the fires of the Muslim camp were extinguished. They would plunder and strike when the Muslims were unprepared. The Muslims, feeling secure and complacent due to their numbers, had no guard in place. As a result, they were taken by surprise when the enemy attacked. Khalid and his men charged at the attackers, cutting down around 100 of them as they attempted to flee back to the fort. However, Yuqanna and his soldiers managed to retreat inside the fort, where they held fifty Muslim prisoners captive.
The next day, Yuqanna paraded the Muslim prisoners and killed them all. In response, Abu ‘Ubaydah ordered that no man entrust his guard duty to anyone else and that everyone must be vigilant, with strict measures in place to prevent further surprises.
The Second Raid: Yuqanna’s Deception
Despite the siege, Yuqanna’s spies, including Christian Arabs fluent in Greek, continued to relay information to him. One spy reported that the about 100 Muslims with only spears were traveling to the Batnan Valley to receive provisions and fodder. Yuqanna saw an opportunity to strike and prepared 1,000 men for another night raid.
Yuqanna’s men, under the cover of darkness, pursued a small group of Muslims traveling with provisions. In the morning, the Muslims, under the command of Munawish, were ambushed by Yuqanna’s forces. Despite a valiant effort, thirty Muslims were martyred, and the raiders seized the Muslims’ provisions and animals. After the battle, Yuqanna’s forces hid in a mountain village to avoid detection by Muslim spies, waiting until nightfall to return to the safety of the fort.
Khalid’s Revenge: The Pursuit of Justice
Initially intending to go alone, Khalid agreed to take Dirar and a small group of men. Upon reaching the battlefield where the Muslims had been attacked, they found the bodies of their fallen comrades, surrounded by the people of the valley who feared retribution. The locals denied any involvement but claimed that a general sent by Yuqanna was behind the attack. After making them swear, Khalid gathered information about the enemy’s route and began pursuing them.
Khalid, guided by Christian locals, followed the trail of the raiders. They waited in a valley and soon heard the sound of hooves. As the enemy forces passed by, Khalid and his men sprang into action. Khalid aimed for the enemy commander, whom he believed might be Yuqanna, and with a single blow, he killed him. The rest of the raiders were overwhelmed and 700 of them were slain by the Muslims. Khalid returned with the spoils of the battle, including 300 prisoners and booty. The following day, Abu ‘Ubaydah set up guards to secure all roads leading to Yuqanna’s fort. As the movement of Muslims was known to the enemy, he asked Kalid to find the spy in their camp. Kalid found a Ghassani Arab Christian, who claimed to be a Muslim, but was unable to recite Quran and later accepted that he was one of the 3 spies. He was given a choice to regret and accept Islam or get killed, and he choose to become a Muslim.
Demis – The Dark Gaint
After 5 months of siege, Yuqanna’s forces continued harassing the Muslims. Abu Ubaydah requested reinforcements from Ameerul Momineen Omar ibn al-Khattab, who sent support from the Kindah and Yemeni tribes, including a towering, fearless warrior named Damis, known as Abu al-Hawl (Father of Terror). He was so tall that his feet dragged the ground when mounted on a horse. Once, he single-handedly defeated 70 raiders from Muhrah, reclaiming his tribe’s wealth, slaves, and animals.
One night, Yuqanna launched a surprise attack with 500 warriors. Damis, leading the Kindah tribe, fiercely countered, chasing them to the fort’s gates and killing 200. Yuqanna retreated, overwhelmed by their ferocity. Abu Ubaydah later ordered Damis to halt, forbidding pursuit in the dark.
Damis’ Leadership and Strategy
Damis proposed a bold new strategy to Abu Ubaydah, asking for 30 brave warriors under his full command. Abu Ubaydah inspired his men by emphasizing unity and faith, urging them to follow Damis despite his status as a former slave. Trusting Damis’ keen insight, Abu Ubaydah organized the troops to create a diversion, allowing Damis and his team to move stealthily toward the fort. Damis demonstrated his tactical brilliance by capturing prisoners for intelligence, although the language barrier complicated communication. Undeterred, Damis captured a Christian Arab who revealed crucial information about internal conflicts and weaknesses within the fort.
Infiltration and Fort Capture
Under the cover of darkness, Damis and 28 warriors executed a daring infiltration by stacking 7 people on top his shoulder forming a human ladder to scale the fort walls. Damis discovered Yuqanna and his officers feasting and chose to wait until dawn for the attack. Before the final assault, he eliminated drunken gatekeepers, opened the gates, and sent messengers to Khalid ibn Walid for reinforcements. As dawn broke, the Muslim warriors launched a surprise attack, shouting “Allahu Akbar!” Their swift actions spread panic among the Romans, who found themselves overwhelmed by the sudden assault.
Fierce Battle and Victory
Despite being vastly outnumbered, the Muslims fought fiercely, with Damis sustaining 73 wounds, all on the front, a testament to his bravery. Only 20 Muslims remained to defend the fort against 500 Roman soldiers until Khalid arrived with reinforcements, turning the tide of the battle. The intense combat ended with the Romans surrendering, pleading for mercy in Greek. Though victory came at a high cost, with the loss of notable companions like Mula’ib bin Miqdam and Hilal bin Umayyah, the Muslims’ perseverance and Khalid’s timely intervention secured their triumph, marking a decisive end to the siege of Aleppo.
Yuqanna’s Conversion to Islam
Following the victory, Abu Ubaydah arrived with the rest of the army. The Romans, seeking mercy, requested indemnity. The Muslims refrained from further violence until Abu Ubaydah made his decision. He ordered the Roman men and women to be brought before him and invited them to accept Islam. Yuqanna, the Roman commander, and several of his officers were the first to embrace the faith. In response, Abu Ubaydah returned their wealth and property, spared the peasants from execution or imprisonment, and required them to pay the Jizyah while living as Muslim subjects. The fort was then emptied, revealing an immense, uncountable quantity of gold and treasures. Abu Ubaydah, now victorious, began contemplating the next strategic move: an attack on Antioch, the imperial headquarters of Heraclius.
Yuqanna’s Remarkable Dream
Yuqanna stood before Abu Ubaydah and spoke fluent Arabic, astonishing everyone present. He attributed the Muslim victory to their faith being the true religion and recognized Muhammad as the Prophet mentioned in the Bible, fulfilling Christ’s prophecy. His sudden fluency in Arabic puzzled Abu Ubaydah, who had heard that Yuqanna previously knew none of the language. Yuqanna then recounted a dream in which he saw a man more handsome than the moon, with a fragrance sweeter than musk. The man, identified as Prophet Muhammad, confirmed his prophetic mission and taught Yuqanna Arabic. Upon awakening, Yuqanna found himself able to speak Arabic fluently. His discovery of a description of Prophet Muhammad in his brother Yuhanna’s books further solidified his belief.
A Pledge of Devotion
Yuqanna declared his faith by saying, “There is no deity besides Allah, and Muhammad is the Messenger of Allah.” Falling into prostration, he praised Allah for guiding him and pledged to fight for Islam with the same vigor he once fought against it. He expressed deep remorse for his past actions, particularly regarding his brother, Yuhanna. Moved by Yuqanna’s sincerity, Abu Ubaydah recited Surah Yusuf (12:92): “There is no blame on you today. May Allah forgive you. He is the Most Merciful of those who show mercy.” He reassured Yuqanna that his sins were wiped clean upon embracing Islam, likening him to a newborn free from sin. With renewed faith, Yuqanna committed himself to the cause, determined to support Islam until his final breath.
‘Amir bin Qubaysah al-Yashkuri narrates from Yunus bin ‘Abdil A’la to whom it was read out that Shahr bin Hawshab narrated from his grandfather, ‘Amir bin Zayd:
I participated with Abu ‘Ubaydah in the conquests of Qinsarin and Aleppo and spent a lot of time with those Romans who entered our Din. I did not see any among them more hardworking, more sincere in his belief, more ambitious in his intentions, more striving in Jihad and more vigorous in battle against the Romans than Yuqanna. By Allah! He was well-meaning towards the Muslims, waged Jihad against the Disbelievers and pleased the Rabb of the Worlds. He achieved such feats against the Romans which no one else of his nationality could do and this was after the Muslims had suffered much at his hands at the Aleppo fort. He had not allowed the Muslims to sleep. He had not spared them day or night and many suffered martyrdom due to him – may Allah be pleased with them all.
