After studying authentic history, I was deeply surprised to find myself admiring Abdullah ibn Ubayy. Having always known him as a 'hypocrite' through the lens of traditional Islamic teachings, it was hard to believe that the real man was, in fact, a noble and humane figure.
I now share some key hidden facts with you so you can judge for yourself, if he was truly a hypocrite, or a misunderstood benefactor of humanity?
Before the arrival of Islam, Medina was ravaged by a brutal civil war between its main tribes, the Aws and the Khazraj. Amid this chaos, one man stood apart—Abdullah ibn Ubayy. He refused to take part in the bloodshed and earned the respect of all sides. His reputation as a peace-seeker made him one of the most admired figures in Medina, both before and after the rise of Islam. Many viewed him as a man of high character, even as a savior of the city.
It is reported about Abdullah ibn Ubayy (link):
Abdullah ibn Ubayy did not participate in the Battle of Bu'ath (the civil war in Medina) because he had a dispute with another chieftain over the killing of Jewish prisoners. It appears that during this conflict, his life was saved by his Jewish allies, the Banu Qaynuqa tribe, as he later proudly stated: "300 armored soldiers and 400 without equipment protected me from every enemy in the fields of Hada'iq and Bu'ath." Ibn Ubayy "made every possible effort to end the civil war between brothers" and succeeded in establishing partial reconciliation between the warring factions, who ultimately accepted his leadership.
Seerat Ibn Hisham also gives the following information about him (link):
Ibn Ishaq narrates on the authority of Asim ibn Umar ibn Qatadah, who said: When the Messenger of Allah, peace and blessings be upon him, arrived in Medina, its chief was Abdullah ibn Ubayy ibn Salul. His honor among his people was undisputed, such that the Aws and Khazraj never united under anyone other than him, whether before or after his time, until the advent of Islam.
Later, during the Prophet’s time, we know that the men of the Jewish tribe Banu Qurayza were executed after surrendering, their wealth was seized, and their women and children were enslaved. But what is less widely known is that Prophet Muhammad initially intended to carry out similar actions against two other Jewish tribes—Banu Qaynuqa and Banu Nadhir.
When the Prophet gave orders for the execution of the Banu Qaynuqa after disarming them, Abdullah ibn Ubayy intervened. He confronted the Prophet directly and pleaded for the lives of his allies. Despite being rebuffed at first, Ibn Ubayy persisted and physically held on to the Prophet's armor, refusing to let go. He warned that executing the tribe would bring future consequences and argued that these same people had once protected him. Eventually, the Prophet gave in and cancelled the execution order, although the tribe was still expelled from Medina.
Seerat Ibn Hisham (link):
The Messenger of Allah [peace be upon him] besieged them for fifteen nights, during which he left Bashir Ibn ‘Abd-Al-Mundhir to take care of the affairs of the Muslims in Madinah, according to Ibn Hisham. He continued to besiege them until Allah cast terror in their hearts, and they were forced to surrender to his command. He ordered that they be tied; and they were put in fetters. ‘Abdullah Ibn Ubayy Ibn Salul went to The Messenger of Allah [peace be upon him] and said: "O Muhammad! Do good to my allies.” They were the allies of Khazraj. The Messenger of Allah [peace be upon him] gave no reply. He said once again: ”0 Muhammad! Do good to my allies.” He turned away from him, thereupon he seized The Messenger of Allah [peace be upon him] by his shield. The Messenger of Allah [peace be upon him] said to him: ”Leave me!” he grew so much angry that the signs (of anger) were visible on his face. He said to him: ”Woe to you! Leave me! Keep your hands off!” he said: ”No, by Allah, I shall not leave you until you do good to my allies: four hundred armorless and three hundred armored have protected me from (all sorts of people, be they) red or black: do you like to kill them all at once? By Allah, I fear the turns of fortune.” The Messenger of Allah [peace be upon him] said to him: ’’They are (released) for you.”
This moment captures the courage and moral clarity of Abdullah ibn Ubayy. He risked his status, his safety, and even the Prophet’s wrath to save hundreds of lives. He did what many others could not. He took a stand against injustice even when it came from the most powerful authority in the land.
It’s important to note that the killing of prisoners has long been condemned, not just in modern times, but even in the pre-Islamic era. To slaughter bound captives was seen as a disgraceful and dishonorable act. Abdullah ibn Ubayy refused to let it happen under his watch.
Thus, based on historical evidence, he appears less like a hypocrite, and more like a principled man who valued peace, justice, and human dignity above all.
Abdullah ibn Ubayy and Sa’d ibn Mu’adh: A Tale of Two Leaders
In Medina, both the Khazraj and Aws tribes had formed alliances with local Jewish communities. The Khazraj were allies of the Banu Qaynuqa, while the Aws were allied with the Banu Qurayza. These alliances played a key role in how events unfolded during Prophet Muhammad's time.
In 5 AH, Prophet Muhammad led an assault on the Banu Qurayza tribe, engaging them in battle for a month before offering them a chance to surrender by laying down their weapons.
One might wonder: Why would Banu Qurayza agree to surrender when Prophet Muhammad planned to execute all their men and allow his fighters to enslave and assault their women? Fighting to the death might have been preferable, as the devastation they faced as captives was far worse than any losses they could have suffered in combat.
The truth is, Banu Qurayza fully understood Prophet Muhammad’s intentions when they surrendered. They knew he aimed to kill them and seize their wealth and property, having already issued execution orders for two other Jewish tribes, Banu Qaynuqa and Banu Nadir. Despite this, they accepted his call to surrender, clinging to the hope that their allies, the Aws tribe, would protect them, just as the Khazraj tribe had saved Banu Qaynuqa and Banu Nadir from slaughter.
Prophet Muhammad, however, was a shrewd and strategic leader. He intentionally chose Sa’d ibn Mu’adh from the Aws tribe to act as the judge, declaring that his verdict would be final. Notably, it was Prophet Muhammad, not Banu Qurayza, who selected Sa’d, and he had a clear motive: he was confident that Sa’d would opt for their execution rather than mercy. The Prophet knew Sa’d’s character better than the Banu Qurayza did.
This confidence was rooted in an earlier event during the Battle of Badr in 2 AH, where the issue of prisoners had surfaced. Sa’d had already revealed his ruthless stance, advocating for the execution of Badr’s captives. The following account highlights Sa’d’s bloodthirsty nature:
History of Tabari, Volume 7, Page 83:
Muhammad ibn Ishaq said: When the verse was revealed, "(Qur’an 8:67) It is not for a prophet to have captives until he has made slaughter in the land," the Messenger of Allah, peace and blessings be upon him, said, "If punishment had descended from the heavens, none would have escaped except Sa’d ibn Mu’adh, for he said, ‘O Prophet of Allah! I prefer to slaughter the (captive) men on a large scale rather than set them free.’"
Indeed, while many of the Prophet’s companions favored sparing the prisoners captured during the Battle of Badr, Sa’d ibn Mu’adh stood out as an uncompromising figure who insisted on their execution. This hardline stance made him a favored figure in the eyes of Prophet Muhammad.
As a result, when Sa’d was chosen to judge the fate of the Banu Qurayza tribe, he fulfilled the Prophet’s expectations by ordering their execution.
Sa’d said: "My judgment is that their warrior men be killed, and their women and children be taken as captives." The Prophet said, "O Sa’d! You have judged concerning them with the judgment of Allah, the King."
And please consider this Qur’anic verse:
(Surah Al-Anfal, Verse 67): "It is not for a prophet to have captives until he has made slaughter in the land. You desire the fleeting wealth of this world, while Allah desires the Hereafter for you."
How can Muslims place the blame for the execution of Banu Qurayza solely on Sa’d when this verse exists? The verse clearly indicates that the command to kill prisoners was not based only on Sa’d’s decision but was rooted in divine instruction, suggesting that it was a prophet’s duty, as ordained by Allah, to execute captives.
In fact, Islamic principles grant a Muslim leader full authority to decide the fate of male prisoners—whether to execute them, enslave them, or demand ransom.
It’s important to note that no historical account suggests Sa’d based his ruling on Torah law, that Banu Qurayza requested a judgment according to the Torah, or that Prophet Muhammad instructed Sa’d to rule by it. The claim that Sa’d’s decision was Torah-based is merely an excuse put forward by some Muslims. The reality is that Sa’d ibn Mu’adh was not a scholar with knowledge of the Torah. Prophet Muhammad himself explicitly stated that Sa’d’s verdict was in perfect alignment with Allah’s judgment. Thus, whether or not the Torah contained such a ruling, the Prophet intended to execute Banu Qurayza, just as he had previously attempted with the Banu Qaynuqa and Banu Nadir tribes.
Some Muslims justify the execution of Banu Qurayza by arguing that, if left alive, they might have conspired against the Muslims and posed a threat. However, this argument is easily countered: Prophet Muhammad could have sold them as slaves to various regions of Arabia, as he did with the Jewish women of Banu Qurayza, who were sold to polytheist men in Najd despite posing no danger to Muslims. Where there’s a will, there’s a way. The truth is, the Prophet had no intention of sparing them, even though there were many alternatives to avoid slaughtering the prisoners.
It is now up to you to decide with an open and honest heart whether Abdullah ibn Ubayy was truly a hypocrite.
Can a hypocrite be someone who, without regard for their own safety, stands up to defend helpless prisoners?
Such a person can only be a true noble Hero, a one who risks their life to save the lives of defenseless, chained captives.
Prophet Muhammad’s Attempts to Have Abdullah ibn Ubayy Killed and the Companions’ Rebellion
Prophet Muhammad attempted to have Abdullah ibn Ubayy killed by Muslims on two occasions, but both attempts failed. The companions themselves (those from Abdullah ibn Ubayy’s Khazraj tribe) rebelled against the Prophet’s orders and provided protection to Ibn Ubayy.
The first incident is the "Incident of Ifk," details of which can be read in English here. This English article is extremely important and must be read.
... Allah's Messenger (ﷺ) got up on the pulpit and complained about `Abdullah bin Ubai (bin Salul) before his companions, saying, 'O you Muslims! Who will relieve me from that man who has hurt me with his evil statement about my family? By Allah, I know nothing except good about my family and they have blamed a man about whom I know nothing except good and he used never to enter my home except with me.' Sa`d bin Mu`adh the brother of Banu `Abd Al-Ashhal got up and said, 'O Allah's Messenger (ﷺ)! I will relieve you from him; if he is from the tribe of Al-Aus, then I will chop his head off, and if he is from our brothers, i.e. Al-Khazraj, then order us, and we will fulfill your order.' On that, a man from Al-Khazraj got up. Um Hassan, his cousin, was from his branch tribe, and he was Sa`d bin Ubada, chief of Al-Khazraj. Before this incident, he was a pious man, but his love for his tribe goaded him into saying to Sa`d (bin Mu`adh). 'By Allah, you have told a lie; you shall not and cannot kill him. If he belonged to your people, you would not wish him to be killed.' On that, Usaid bin Hudair who was the cousin of Sa`d (bin Mu`adh) got up and said to Sa`d bin 'Ubada, 'By Allah! You are a liar! We will surely kill him, and you are a hypocrite arguing on the behalf of hypocrites.' On this, the two tribes of Al-Aus and Al Khazraj got so much excited that they were about to fight while Allah's Messenger (ﷺ) was standing on the pulpit. Allah's Messenger (ﷺ) kept on quietening them till they became silent and so did he.
The second incident is as follows:
It was said to the Prophet (ﷺ) "Would that you see `Abdullah bin Ubai." So, the Prophet (ﷺ) went to him, riding a donkey, and the Muslims accompanied him, walking on salty barren land. When the Prophet (ﷺ) reached `Abdullah bin Ubai, the latter said, "Keep away from me! By Allah, the bad smell of your donkey has harmed me." On that an Ansari man said (to `Abdullah), "By Allah! The smell of the donkey of Allah's Messenger (ﷺ) is better than your smell." On that a man from `Abdullah's tribe got angry for `Abdullah's sake, and the two men abused each other which caused the friends of the two men to get angry, and the two groups started fighting with sticks, shoes and hands. We were informed that the following Divine Verse was revealed (in this concern):-- "And if two groups of Believers fall to fighting then, make peace between them." (49.9)
Despite the Qur’an and Prophet Muhammad repeatedly labeling Abdullah ibn Ubayy as the "leader of the hypocrites" and even directly ordering his killing (in the Incident of Ifk), Abdullah ibn Ubayy commanded such immense respect among his people that the companions rebelled against the Prophet’s orders to provide him protection.
Prophet Muhammad’s Covert Operations to Eliminate Jewish Critics, but not killing Abdullah Ibn Ubai
With the two major pagan Arab tribes of Medina embracing Islam and uniting under Prophet Muhammad’s leadership, Muslims gained absolute dominance over the Jewish tribes in the city.
As a result, any Jewish leader in Medina who openly criticized Prophet Muhammad’s prophethood was secretly targeted for assassination. Here are some notable examples:
- Abu Afak
Background: An elderly Jewish poet in Medina who composed verses criticizing Prophet Muhammad’s policies.
Incident: It is reported that the Prophet asked his companions, “Who will rid me of this wicked man?” In response, a companion named Salim ibn Umayr assassinated Abu Afak at night.
Source: Ibn Sa’d’s Kitab al-Tabaqat al-Kabir, Seerat Ibn Hisham. - Asma bint Marwan
Background: A female poet in Medina who wrote poetry critical of Prophet Muhammad and the Muslims.
Incident: According to narrations, the Prophet ordered her assassination. Umayr ibn Adi carried out the killing while she was nursing her children.
Source: Ibn Sa’d’s Tabaqat. - Ka’b ibn al-Ashraf
Background: A member of the Jewish Banu Nadir tribe, Ka’b wrote poetry against Prophet Muhammad and incited the Meccans to oppose the Muslims.
Incident: The Prophet devised a plan for his elimination. A group led by Muhammad ibn Maslama tricked Ka’b into meeting them and then killed him.
Source: Sahih Bukhari (Book of Military Expeditions), Seerat Ibn Hisham. - Abu Rafi (Sallam ibn Abi al-Huqayq)
Background: A Jewish leader from Khaybar who financially supported tribes opposed to Prophet Muhammad.
Incident: The Prophet tasked a group of companions with his assassination. Abdullah ibn Atik and others traveled to Khaybar and secretly killed him.
Source: Sahih Bukhari (Book of Military Expeditions).
Despite Prophet Muhammad’s intense animosity toward Abdullah ibn Ubayy, he failed to have him assassinated throughout his life. Unlike the Jewish leaders who belonged to weaker tribes, Abdullah ibn Ubayy was a prominent figure from the powerful Muslim Khazraj tribe. Despite the Prophet’s deep hostility, Abdullah commanded immense respect among his people, making it impossible to target him in the same way.
Abdullah ibn Ubayy’s Death in 9 AH and Prophet Muhammad Providing His Shroud
A question was asked:
You claim that Prophet Muhammad (peace be upon him) harbored deep animosity toward Abdullah ibn Ubayy, yet he provided a shroud and led his funeral prayer upon his death. Doesn’t this act prove that the Prophet was a compassionate humanitarian who, out of sheer humanity, performed the funeral prayer even for his enemy?
Response:
It is true that Prophet Muhammad made several attempts to have Abdullah ibn Ubayy eliminated during his lifetime.
Despite these efforts, Abdullah ibn Ubayy continued to live in Medina, and neither the Prophet nor any other Muslim had the resolve to kill him. He passed away in 9 AH, just one year before the Prophet’s own death.
Remarkably, even in his final days, Abdullah ibn Ubayy commanded immense respect among his people. Despite repeatedly labeling him the “leader of the hypocrites,” the Prophet led his funeral prayer and had his body exhumed to drape it in his own shirt. However, these actions were driven by political motives, not pure altruism.
The Prophet (ﷺ) came to (the grave of) `Abdullah bin Ubai after his body was buried. The body was brought out and then the Prophet (ﷺ) put his saliva over the body and clothed it in his shirt.
Narrated `Umar bin Al-Khattab: When `Abdullah bin Ubai bin Salul died, Allah's Messenger (ﷺ) was called in order to offer the funeral prayer for him. When Allah's Messenger (ﷺ) got up (to offer the prayer) I jumped towards him and said, "O Allah's Messenger (ﷺ)! Do you offer the prayer for Ibn Ubai although he said so-and-so on such-and-such-a day?" I went on mentioning his sayings. Allah's Messenger (ﷺ) smiled and said, "Keep away from me, O `Umar!" But when I spoke too much to him, he said, "I have been given the choice, and I have chosen (this) ; and if I knew that if I asked forgiveness for him more than seventy times, he would be for given, I would ask it for more times than that." So Allah's Messenger (ﷺ) offered the funeral prayer for him and then left, but he did not stay long before the two Verses of Surat-Bara'a were revealed, i.e.:-- 'And never (O Muhammad) pray for anyone of them that dies.... and died in a state of rebellion.' (9.84)
So, why did the Prophet lead Abdullah’s funeral prayer and provide a shroud despite their enmity? Was this purely an act of humanity to ensure his enemy’s salvation?
To understand this, we must recognize that Prophet Muhammad was a highly astute and politically savvy leader. He developed a strategy: when faced with the need to oppose or manage conflicting groups, he avoided direct confrontation. Instead, he relied on “divine revelation” to navigate disputes. For example:
- When women complained about their husbands beating them, the Prophet initially banned such actions to gain their support.
- However, when men grew upset, realizing their support was more critical, he permitted wife-beating through a new revelation.
- Similarly, when women objected to being slapped, the Prophet banned it at their request but later allowed it via revelation to appease the men.
These details about domestic issues are elaborated in our related article here:
This pattern of using revelation to achieve his objectives is evident across many issues.
At the time of Abdullah ibn Ubayy’s death, his influence was so significant that the Prophet could not risk alienating the Muslim companions from Abdullah’s Khazraj tribe. Despite his deep enmity toward Abdullah, the Prophet employed his familiar tactic:
- On one hand, despite Umar’s vocal objections, he provided his shirt as a shroud for Abdullah to ensure that Abdullah’s son and the Khazraj tribe remained loyal.
- On the other hand, to placate Umar (representing the Muhajireen) and the Aws tribe of the Ansar, he claimed a new revelation prohibiting funeral prayers for hypocrites or standing at their graves.
By invoking revelation, the Prophet skillfully balanced the interests of all parties.
Do you still believe the Prophet led Abdullah’s funeral prayer purely out of humanitarian concern, hoping to secure his enemy’s place in paradise? Or does it seem more likely that he used the shroud, saliva, and funeral prayer as political gestures to get support from both parties? If he was really such a humanitarian, why did then he ordered killing his political Jewish opponents (who belonged to weaker tribes) through covert operations?
This leads to another question: If Allah knew full well that Abdullah ibn Ubayy was the “greatest hypocrite,” why did He not command his execution in the Qur’an during his lifetime? At the very least, why not openly declare Abdullah’s hypocrisy in the Qur’an while he was alive?
Hassan Radwan