A generation-old theoretical foundation continues to dominate Jewish educational literature, creating a widening gap between established frameworks and contemporary educational needs. Through critical analysis of four influential works - Cohen's "Jewish Education in Democratic Society," Weinstein and Yizhar's "Modern Jewish Educational Thought," Kadushin's "Worship and Ethics," and Wolf's "Rediscovering Judaism" - fundamental tensions emerge between progressive educational approaches and institutional realities. While Cohen advocates for communal over denominational schooling, this solution inadequately addresses systemic challenges including poor teacher training, substandard materials, and weak oversight. Most significantly, current reform proposals overlook a crucial philosophical divide: the pragmatic orientation of American education versus the intrinsic value system inherent to Jewish education. The scholarly examination reveals that successful Jewish educational reform demands recognition of this fundamental philosophical difference, stronger practical implementation of theoretical principles, and deeper consideration of how Jewish and general education intersect. Without confronting these foundational issues, organizational restructuring and curricular changes alone cannot produce meaningful reform.