In the decades before and after Rome's destruction of Jerusalem in 70 CE, the Sicarii emerged as a militant Jewish resistance group whose legacy would echo through centuries of Jewish legal thought and nationalist movements. While initially known for targeted assassinations using concealed daggers against both Roman occupiers and Jewish collaborators, the term "Sicaricon" evolved in Talmudic literature to address broader issues of land seizure and property confiscation in the wake of Roman conquest. Through analysis of Josephus's historical accounts and Talmudic sources, this research traces how Jewish tribunals, particularly under Rabbi Judah the Prince, developed sophisticated legal frameworks to address wartime property disputes and establish precedents for determining legitimate ownership and compensation. The methodology combines historical documentation with rabbinic legislative analysis to examine the evolution of property laws concerning confiscated Jewish lands. These ancient legal precedents regarding forced property transfers and communal survival strategies reveal striking parallels between historical Jewish responses to persecution and contemporary struggles for national liberation, illuminating recurring patterns in Jewish historical experience across different epochs.