Yazid b. Muawiyah is infamously known as the person behind the killing of Prophet Muhammad’s grandson Husayn and more than seventy accompanying people, most of whom were Muhammad’s descendants in 680. The succession conflict between Husayn’s father ‘Ali and Yazid’s father Muawiyah decisively divided the Muslim community along Sunni and Shiite sectarian lines. The murder of Husayn was the single most traumatic event in the history of Islamic sectarianism and is commemorated each year by the Shiites by extensive mourning rituals. Cursing Yazid had become a widespread practice since Husayn’s murder and a feature that showed one’s devotion to Shiism. Cursing was widespread among the Shiites and not unknown among the Sunnis throughout the medieval period. However, the medieval giant of Sunni thought, al-Ghazzali, who is said to revive the traditional teaching of Islam, discouraged Muslims from cursing Yazid, arguing that he was a practicing Muslim. Ghazzali and like-minded scholars saw Yazid only as a sinner, but still a true Muslim. As the upholders of Sunni orthopraxy, the Ottoman juriconsults such as Ebussuud also discouraged Muslims from this practice. Yet, were they successful in their attempts? How common was cursing Yazid among the Ottomans and what does it tell us about Ottoman Sunnism? In this paper, based on various historical and literary sources from the empire’s early years to mid-seventeenth century, through the lenses of conflicting readings of Yazid’s persona and acts, an attempt will be made to show multi-faceted, ambivalent, and often contradictory nature of Ottoman Sunnism. Rather than reducing Ottoman Sunnism to a narrow and unilateral interpretation, as has been conventionally done, this paper will point out to the strength and resilience of pro-Alid sentiments in the Ottoman Empire despite the continuous efforts of champions of Ottoman Sunni ideology.