How do presidents decide to delegate? Research on unilateral powers has (often informally) assumed that executive orders start and end with the president, but as in all principal-agent relationships, executives rely on subordinates to carry out their directives. Political scientists have explored when and why Congress delegates to the president, but such action often necessitates a response from the White House; namely, the president delegates to the bureaucracy the authority delegated to him by Congress. Bureaucrats may in turn have a wide degree of latitude when implementing the president’s orders. I argue that presidents must make strategic decisions in choosing to whom to delegate, much in the same way that Congress makes certain calculations in deciding whether to delegate to the executive branch.