Background/Context: Since the early 1990s, the United States has been witnessing reforms in large, high-visibility cities, with mayors granted the power to appoint school boards, superintendents, or both. This shift away from elected school board governance has been characterized as marginalizing traditional educators and ushering in reforms that traditional educators oppose. On the other hand, Japan’s experience with mayoral control of schools is nationwide and longer-lived. In 1956, mayors were given authority to appoint members of the school board, and in 2015 they were given further authority to appoint school superintendents. Purpose/Objective/Research Question/Focus of Study: This study analyzes whether Japanese mayors appoint superintendents whose backgrounds make them likely to challenge the education establishment and introduce dramatic educational reforms. We provide some early evidence on how mayors have been using their new powers and how they interact with the superintendents they select. Research Design: We used data from nationwide surveys conducted by the Japanese government to map the broad pattern of superintendent characteristics over time as well as for a sampling framework to identify and select a smaller number of superintendents to be interviewed for obtaining in-depth information. Semistructured interviews of six superintendents were conducted to delve more deeply into the relationship between mayors and superintendents, and the communication between the superintendents and the school board members in Japan. To triangulate the interview data, transcripts of school board meetings, city council meetings, election bulletins (official campaign manifestos), demographic data, and national test scores of students were collected from 2015 to 2019. Conclusions/Recommendations: We identified important differences between the United States and Japan. Rather than aligning with the reform-oriented mayors against school boards and education bureaucracies, the Japanese mayor-appointed superintendents act as mediators between the mayors and the school boards. The difference may be that, in the United States, only mayors who sought mayoral control had the right to appoint school superintendents, whereas in Japan the national government gave all mayors the right to appoint superintendents, regardless of the political context.