Abstract: By outlining the history of administrative law from the Progressive era to present, this essay suggests a genealogical connection between Dewey’s pragmatism and democratic experimentalism. Democratic experimentalism is rooted in the Progressive paradigm of an administrative state guided by expert judgment but responds to the ossification of the U.S. administrative state. Connecting democratic experimentalism to Progressivism provides the background for some speculations about the politics that might be needed for democratic experimentalism to have successes equivalent to those of Progressive administrative law.