In al-Narshakhi’s accounts of the earliest Muslim raids against Bukhara, the author presents us with two related anecdotes in which the Bukharan Queen Khatun meets the Arab general `Abdallah b. Khazim. In the first, Khatun was asked to greet each of the Arab commanders as a stipulation of her surrender. When she was brought before Ibn Khazim, he had prepared a dramatic tableau. He sat in his tent behind a roaring fire which reflected off his eyes so they looked red, dressed in his armor with his unsheathed sword placed before him. Khatun fled in terror at the sight. In the second, following another successful attack on Bukhara, Khatun asked to see Ibn Khazim again for he had previously frightened her so, declaring that “It seems to me he is not human.” The image of Ibn Khazim as a skilled general with a flair for the dramatic appears elsewhere in our sources for the conquest of Khurasan and Transoxiana, alongside stories of his rebellious nature. During both the First and Second Fitnas, Ibn Khazim seized control of Khurasan with a mix of guile and force. In the latter instance, he is accused of killing up to one fifth of the Arab garrison in Khurasan as he consolidated his own authority. His son Musa is no less of a character, known for his adventures among the Sogdian lords of Transoxiana and his conquest of Tirmidh, which he ruled for fifteen years as his own private kingdom and a refuge for rebellious Arabs and Iranians. This paper examines the textual sources for Ibn Khazim’s adventures in Khurasan and how these accounts balance the image of a dramatic hero responsible for numerous Muslim victories including the conquests of Nishapur and Sarakhs and the defeat of the resistant Parthian general Qarin with the rebel who twice took the governorship of Khurasan for himself, refused to acknowledge Umayyad rule, and encouraged his son to join the Sogdians with the treasury of Marw. In these accounts, we can see division among the Arabs from the outset of the conquest of Iran and perhaps learn how historians not only dealt with divisiveness in the early conquests but also how they rehabilitated the problematic ancestors of families who maintained prominent positions centuries later.