Rabbi Joseph Baer Soloveitchik's hermeneutical methodology (Derush) represents far more than scholarly ornamentation - it emerges as a vital bridge between Western philosophical thought and traditional Judaism. Through textual analysis of Soloveitchik's major works, particularly "Kol Dodi Dofek," a distinct pattern emerges where Biblical interpretation serves as an existential necessity rather than mere academic exercise. This interpretive approach follows a rich historical trajectory from Philo of Alexandria through medieval Jewish philosophy, where Derush has consistently mediated between traditional Jewish sources and external philosophical challenges. Unlike the compartmentalized "Torah and Derekh Eretz" approach, Soloveitchik develops what can be termed "creative hermeneutics," transforming Biblical texts and Halakhic principles into a natural language for expressing modern philosophical concepts. This methodology enables Soloveitchik to expand Halakhah into a comprehensive philosophical-existential system that authentically addresses contemporary religious experience while maintaining deep fidelity to traditional Jewish sources. The analysis reveals that Derush functions as a substantive component essential to his thought rather than an external interpretive tool, offering a unified intellectual framework that synthesizes Western culture and Halakhic Judaism.