This Essay examines the ways in which the Supreme Court’s October 2021 Term challenges core theoretical commitments of progressive constitutional theory. Progressive constitutional theory originated in the progressive political theory of the late nineteenth and early twentieth centuries. Accordingly, progressive constitutional theory shares progressive political theory’s commitments to two propositions: rationalism and individualism. These commitments lead to an understanding of history as moving in a particular direction—one that is generally in line with progressive ideology. The originalist and traditionalist approaches of the Court’s October 2021 decisions call into question the progressive confidence in the direction of history while simultaneously rejecting the rationalistic and individualistic premises of progressivism. This helps explain why many progressive constitutional theorists have found the Court’s decisions so disorienting and confounding. The October 2021 Term challenged—even though it did not definitively refute—the progressive narrative of constitutional redemption through history. The implications of the Court’s decisions will reverberate through American constitutional theory for decades to come.