During the Third Crusade, Roland zealously pursued one of the keys to the Temple of the Sand. His fixation manifested in a series of brutal interrogations that, according to the Assassin Hamid, earned him a reputation for depravity and viciousness.
His local infamy, alongside the unprecedented level of security surrounding the hospital, agitated the attention of the Assassins, and in 1190, they sent one of their own into the stronghold to investigate. The infiltrator failed to return however, and the Assassins' intel on Roland's operations remained scarce.
A few months later, the Assassin Altaïr Ibn-La'Ahad, in his quest for the Chalice, arrived in Tyre after Fajera advised him to seek an old man held captive at the city's hospital. Roland was convinced that this old man, having been to the Temple himself, knew the whereabouts of a key to the Temple. While he commenced the interrogation of his prisoner, Altaïr infiltrated the hospital through the sewers and subsequently the lower furnace rooms. Although the doctor was privy to this underground route, his guards ultimately failed to subdue the Assassin. As a result, his interrogation was interrupted by Altaïr's arrival in the detention room.
Snapping at his stupefied guards to kill the Assassin, the doctor retreated to an upper platform, seeing little means of escape. It was in vain, as Altaïr slew his few guards with ease and climbed up to confront him. Defenseless in the face of the Assassin, Roland could only curse at him before being assassinated from a chandelier.