In "Chevron, U.S.A. v. Natural Resources Defense Council, Inc.", the Supreme Court famously held that judicial deference to agency interpretations of ambiguous statutes is appropriate largely because the executive branch is politically accountable for those policy choices. In recent cases, the Court has not displayed unwavering commitment to this decision or its principle of political accountability. This Article explores "Gonzales v. Oregon" as well as an earlier case, "FDA v. Brown & Williamson Tobacco Corp.", in which the administrations possessed strong claims of accountability yet the Court did not defer to the agency determinations. In both, the Court justified its refusal of deference by contending that the questions were too extraordinary for Congress implicitly to have delegated. This Article argues that these cases might be better understood to reflect a judgment not about whether Congress had delegated interpretive authority, but about how each administration had exercised its authority. Both administrations, while accountable in a general sense, acted undemocratically when viewed in the particular context. They used broad delegations in ways insensitive to likely congressional or popular interests on controversial issues, and inconsistent with the obligations of the executive branch within government. The Court determined that the conditions for judicial deference were not met. Thus, these cases reflect an approach that, while inconsistent with conventional notions of political accountability, is nevertheless principled and defensible. The Article shows that this approach is reflected in other cases, although not many. The infrequency does not diminish the importance of the message that the cases send to the executive branch. But it does illuminate important limits: Ordinarily, administrations do not raise alarms, and political accountability is sufficient for judicial deference. An examination of the cases demonstrates that the Court is aware of the danger that it might invalidate agency interpretations based simply on the Justices' own ideology or politics, and that it has taken steps to curb such judicial overreaching.