Ibn Ubayy was one of the chiefs of the Khazraj, who then were in conflict with the other major Arab tribe of the city, the Banu Aws.
[1][2] It appears that at one point during the conflict, his life was saved by his Jewish allies from the tribe of Banu Qaynuqa, as he would later exclaim: "300 soldiers armed in mail, and 400 unequipped, -- they defended me on the fields of Hadaick and Boath from every foe.
[1][8][9] However, according to Rodinson, Ibn Ubayy may have converted out of a "genuine sympathy with monotheist ideas fostered by his friendly relations with the Jews".
[5] Ibn Ishaq writes that some of the Ansar "were not altogether convinced of the political wisdom of supporting the apostle: these came to be regarded as paying lip-service to Islam, but hiding treachery in their hearts, and they were known and reviled as 'the Hypocrites'".
Ibn Ubayy replied:[3] Nay [...] I will not let thee go, until thou hast compassion on my friends; 300 soldiers armed in mail, and 400 unequipped, - they defended me on the fields of Hadaick and Boath from every foe.
As for me, I am one verily that feareth the vicissitudes of fortune.Then, Muhammad acceded to his request and gave the Banu Qaynuqa three days to leave the city.
Rodinson considered it as threat against Muhammad,[16] Watt that Ibn Ubayy "urged their importance as a fighting unit in view of the expected Meccan onslaught".
[1] Muslims have traditionally seen the episode as another piece of evidence for Ibn Ubayy's hypocrisy since he insisted that adherence to Islam had not completely severed the old obligations of tribal and personal loyalty.
[18][20] According to Watt, Surah 3:166 interprets Ibn Ubayy's withdrawal as showing "cowardice and lack of belief in God and the Prophet"[1][21] Muhammad's 700 men met the 3000 of the Quraish in the Battle of Uhud and were defeated.
The Quraish, however, did not succeed in killing Muhammad, and did not attempt to occupy the town of Medina, possibly because they knew it was guarded by Ibn Ubayy.
Waqidi reports that Ibn Ubayy, at first, strove to bring about a reconciliation, and Tabari relates that Abd-Allah accused Muhammad of treachery and urged the Nadir to resist by promising aid.
On the march home, conflict arose between the Muhajirun and the Ansar when a Bedouin servant of Umar pushed an ally of the Khazraj.
Hearing of this, Ibn Ubayy reportedly voiced his discontent:[27] This... ye have brought upon yourselves, by inviting these strangers to dwell amongst us.
After Muhammad had announced that he had received a revelation confirming Aisha's innocence, he had her three of her accusers, who had come forward, punished by eighty lashes.
[32] In 630, when Muhammad launched a campaign against the Byzantine Empire during a time of drought and food shortage created serious discontent in Medina, Ibn Ubayy expressed his sympathy for those criticizing the expedition as untimely.
As the army assembled, Ibn Ubayy's troops formed a separate camp and turned back to Medina when Muhammad's forces set out.
And Allah guides not those people who are rebellious (80).Ibn Ubayy's death signalled the end of the so-called Munafiqun faction, as "there was no one left ... possessed of power or influence".