The Tale Of A Jail-Break And Assassination Carried Out By Prisoners From Constantinople

In the mid-7th century, the realm of the emperors of Constantinople came under attack from aggressive Arab armies. During the reign of the first caliph, Abū Bakr (r. 632-634), Arab forces began expanding into the regions of Jordan, Palestine, Syria and Iraq, and these expansionist wars increased dramatically during the reigns of Umar I (r. 634-644) and Uthman (r. 644-656). Mind you, this new wave of warfare hit the emperors of Constantinople just after they had been exhausted from a destructive war with Persia that lasted from 602 to 628, and was compounded by an ongoing struggle with the Lombards in Italy that had been raging since King Alboin led his Lombard people into Constantinople’s Italian lands around 568. Suffice it to say, the military might of Constantinople had been depleted over the decades of war, and its resources and morale were being stretched thin after so many conflicts. Taking advantage of Constantinople’s weakened state and the growing discontent in the empire (causing the further trouble of rebellions), the Arab forces had success in winning battles and seizing land from the Empire of Constantinople. The formidable but increasingly ill Emperor Heraclius (r. 610-641), who had previously brought the empire of Persia to its knees, now found he could do little but try to defensively mitigate the damage of invasion, while also striving to fortify and garrison Anatolia. Yet, Emperor Heraclius could only do so much before he died in 641, and his immediate successors proved to be a destabilizing and ineffective bunch, causing more vulnerabilities and rebellions that were taken advantage of by the empire’s opportunistic rivals. Arab conquests and victories in battle, in turn, caused a great many prisoners to fall into the hands of the Arab forces.

By 654 or 655, during the reigns of Emperor Constans II of Constantinople (r. 641-668) and caliph Uthman (r. 644-656), many warriors fighting on the side of Constantinople had been captured by the Arab forces and were being held as prisoners of war. The skilled general and future Umayyad ruler, Muawiyah (or Mu’awiya), in particular, had taken a great many prisoners and he reportedly decided to funnel a large portion of his captives to a camp in the region known as Phoenician Tripolis. Muawiyah appointed a deputy to oversee the prisoners who were gathered in the area while he personally continued waging his military campaigns elsewhere. The absence of Muawiyah at Tripolis, however, gave local dissidents a chance to cause some disruptions in Tripolis.

As the story goes, two local brothers (identified as the sons of a certain Bucinator) led a prison-break that freed the captives at Tripolis. Their plot was evidently a great success and caught the local authorities completely by surprise. After being freed and armed to some extent, the army of prisoners was said to have charged their way to the location of the leading official in Tripolis. This local leader was reportedly killed by the rioting prisoners, and after the killing was done, the prisoners retreated from Tripolis, setting out in hopes of returning to the heartland of the empire of Constantinople. This curious incident was recorded by the chronicler, Theophanes (c. 750-818), who wrote:

“In this year [Annus Mundi 6146 / 654-655 CE] Muawiyah ordered a great force of ships readied for an expedition against Constantinople. All this preparation took place in Phoenician Tripolis. Two Christ-loving brothers—the sons of Bucinator—who were staying in Tripolis noticed this. Overcome by divine zeal, they hurried to the city’s prison (which held a host of Roman prisoners), broke open its gates, and rushed against the city’s emir. They killed him and his men, burned all their gear, and sailed to Romania” (Theophanes, Chrtonographia, entry for Annus Mundi 6146).

According to Theophanes, the sons of Bucinator successfully escaped Tripolis and eventually reached Constantinople, where they joined the entourage of Emperor Constans II. As for the Arab response to the prison break, Muawiyah kept a level head while he regained control of the situation. He sent a new deputy to oversee the city and to resume gathering supplies and troops for future military operations. The prison break, despite killing the previous local leader and destroying some supplies, apparently did not do too much damage to Tripolis and its stockpiles, for the new leader appointed to the region was quickly able to start using Tripolis as a base from which to attack the forces of Constantinople.

Written by C. Keith Hansley

Picture Attribution: (Illustration of Constantinople from Cassell’s Illustrated Universal History, c. 19th century, [Public Domain] via Creative Commons, Europeana and The British Library).



  • Theophanes, The Chronicle of Theophanes, translated by Harry Turtledove. Philadelphia: University of Pennsylvania Press, 1982.

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