Israel's Masorti (Conservative Jewish) movement stands at a critical crossroads, caught between its aspirations for religious pluralism and the entrenched dominance of Orthodox Judaism in Israeli society. As calls emerge for increased political engagement, including Michael Graetz's proposal to form a dedicated Masorti political party, fundamental questions arise about the movement's strategic direction. Through qualitative analysis of institutional barriers, cultural perceptions, and strategic choices, multiple obstacles to Masorti success become clear: the Orthodox rabbinate's monopolistic control through state-sanctioned authority, chronic underfunding relative to Haredi institutions, authenticity challenges favoring traditional Orthodox appearance, organizational fragmentation across Jerusalem, and an internalized marginalization evidenced by the relocation of egalitarian services from the Western Wall to the Southern Wall. While Haredi political parties effectively leverage electoral power to secure budgets and maintain religious authority, evidence suggests that forming a Masorti political party would likely backfire, risking both ideological compromise and electoral defeat, as demonstrated by the failed Meimad party experiment. The path forward appears to lie not in formal political engagement but in sustained grassroots advocacy, unified messaging, increased diaspora support, and strategic legal challenges to gradually advance religious pluralism in Israeli society.