This Essay challenges the conventional wisdom that political accountability is sufficient to check abuse of power and lawlessness in the executive branch in the vast areas of executive action that are not regularly subject to judicial review. The Essay studies two examples in the long history of partisan appointment of high-ranking government lawyers (Roger Taney’s work for Andrew Jackson in the dispute over the Second National Bank, and the recruitment and work of agency lawyers in the first wave of the New Deal) to demonstrate that lawyers working in the Bush Administration Department of Justice were unique neither in their attitude toward constitutional constraints on the executive, nor in their identification with and desire to promote the Administration’s agenda. Nearly exclusive reliance on political accountability invites an ideologically charged approach to the provision of legal advice to the President, particularly in times of national crisis when the President’s practical and constitutional powers—his “authority of initiative”—are at their peak. The result is that lawyers charged with exercising independent professional judgment to define and preserve the boundaries of permissible executive branch action often assist the President in moving, manipulating, or simply ignoring these boundaries and hence altering the very framework in which controversial executive action is assessed after the fact. In areas in which transparency ensures the supervision of Congress and the electorate, this “extralegal” approach to law reform is less controversial. But in areas such as national security, where transparency is weak at best, the danger of unchecked lawlessness is acute indeed. The Essay considers structural options to ensure that the Department of Justice provides genuinely independent legal advice.