Byzantium experienced a major crisis in the seventh-century AD; they were losing significant territories to Arabic forces and Christian followers to Islam. Moreover, Emperor Constans II (r.641-668) was being opposed within his own empire regarding Christological issues from Pope Martin (r.649-655) and Abbot Maximus the Confessor (c.580-662), who defied his Typos and held the 649 Lateran Council. Thus, both men were exiled and punished as a result of their unruly nature. In this paper I compare the two trials of Martin and Maximus, showing that Maximus’ unprecedented three exiles and amputations were more than a reflection of the seventh-century crisis. I argue that Maximus’ punishment was not just a reflection of his time, but that Constans II exercised his religious authority in punishing Maximus, who called his divine nature into question. Maximus was sent into exile three times, which alluded to a return to the desert, just like Saint Anthony and Athanasius earlier. Scholars argue that Pope Martin’s punishment was made a public spectacle; similarly, I argue that Constans II tailored Maximus’ punishment to correct the ‘unruly’ monk following both secular and monastics laws. Methodologically, I cite the 451 Chalcedon council, Saint Basil’s Rule, andJustinian’s Laws.