The deportation of 1,615 Jewish residents from the island of Rhodes and 94 from its neighboring island of Kos on July 24, 1944, a few days after the last major deportation from Hungary had occurred, transpired to be the final transport to Auschwitz to leave the Greek mainland. This last deportation is acknowledged in Holocaust literature, but its significance for our understanding of the Nazi genocide of the Jews remains largely overlooked. The timing of the deportation, when it was clear to the German military elite that Nazi Germany had lost the war (triggering the attempt to assassinate Hitler), raises important questions in relation to contingency and ideology in providing the context and motive for the genocide. This chapter argues that by the summer of 1944, the factor of timing - and the lost war against the Allies - had become the motor of destruction against the enemy within Germany’s grasp: the Jews. This aspect provides the narrative framing for this chapter which also examines other overlooked factors, each playing its part in the fate of the Jews of Rhodes, not least that of Greek-Dodecanese nationalist aspirations and how these impacted on intercommunal relations on the island.