This Article analyzes whether President Bush's charitable choice executive orders, which permit religious organizations to apply for federal funds to deliver social services, are a permissible exercise of presidential power. Although Congress has enacted charitable choice provisions in some major statutes, including a 1996 welfare reform act, it debated but did not extend charitable choice throughout the entire federal human services bureaucracy, as the President's executive orders do. The core question this Article examines is whether President Bush's charitable choice executive orders constitute permissible gap-filling of ambiguous statutes under the Chevron doctrine or impermissible exercises of executive lawmaking under Youngstown Sheet & Tube Co. v. Sawyer. This Article analyzes possible statutory delegations to the executive branch, including human services statutes and federal procurement laws and concludes that they do not contain gaps that give policy-making discretion to the President. With regard to constitutional authority for the orders, recent Supreme Court case law makes clear that charitable choice programs are not constitutionally compelled. Article II of the Constitution, which gives the President the authority to take care that the laws are faithfully executed, is another possible source of authority, but its bounds are ill defined. Fans of a strong executive argue that presidential policy-making best serves constitutional values of accountability and efficiency. This Article tests these assumptions and finds that the charitable choice executive orders not only fail to further these values, but actually may undermine them. Accordingly, the Article concludes that the charitable choice executive orders constitute an unlawful aggrandizement of executive power.