Catholic schooling in the United States is suffering from a persistent enrollment crisis that has triggered the need for system-wide organizational reforms. However, most of the changes that the sector has experienced has taken place in individual schools making decisions about how to operationally sustain their individual school community. In this article, we present findings from a qualitative analysis of 26 superintendents of (arch)diocesan Catholic school systems in order to better understand why there has been an absence of system-level change in the Catholic sector in the U.S. at a time when systems thinking has started to spread throughout other sectors domestically and internationally. We show through the findings presented in this paper that many Catholic school systems in the United States do not sustain system-level change because they rely on a decentralized "system of schools" organizational form that superintendents believe limits the possibility for sector-wide organizational reform. We highlight in this paper the ways superintendents are forced to navigate these organizational and political limitations and suggest what the implications of this limited possibility for system-level change are for the Catholic sector and other similarly organized sectors.