Bottom-up reform as a policy strategy for decades has faltered in implementation. This article starts from the premise that these disappointing results stem from researchers' and practitioners' almost exclusive focus on implementation in schools or on what some call "the bottom" of hierarchical education systems but not shifts in policy makers' roles that might enable school change - the "up" in bottom-up reform. These gaps are addressed with a strategic, comparative case study of city-level policy makers in bottom-up reform implementation in Oakland, California, during the 1990s. The author demonstrates that organizational learning theory defines basic dimensions of policy makers roles in implementation and that they faced four paradoxes in adopting these roles. Over time, they tended to favor avenues consistent with traditional top-down, not bottom-up, policy making. Findings highlight policy makers as important participants in bottom-up reform implementation and suggest that new institutional supports for them may enable implementation.