A centuries-old paradox lies at the heart of Jewish law: apostates who convert to other faiths retain their halakhic Jewish status in matters of marriage, divorce, and inheritance, creating profound tensions between religious identity and communal boundaries. Analysis of Talmudic, Geonic, and medieval sources reveals that the term "meshumad" initially described Jews who violated specific commandments rather than converts to other religions. This meaning shifted during the Geonic period as rabbis grappled with forced conversions under Islamic and Byzantine rule. Rashi's pivotal ruling that "Israel, even though it has sinned, is still Israel" became the foundation for maintaining Jewish status regardless of religious practice. Yet this position has created increasingly complex theological challenges, exemplified by the Brother Daniel case and ongoing debates about Jewish converts to Christianity and Islam. Through extensive examination of rabbinic literature, the research identifies a potential resolution: modern halakhic authorities could reclassify apostates as "minim" (heretics) rather than "meshumadim," allowing their formal exclusion from the Jewish community. Such reclassification would better reflect contemporary Jewish consciousness while preserving the essential connection between Jewish peoplehood and religious identity.