Purpose: Pursuing a decentralized approach to system organization is increasingly popular. For example, several large districts in the U.S. have implemented portfolio-managed approaches to system organization designed to enhance school leaders’ authority by enhancing system leaders’ oversight responsibilities. But there is an open question about how organizational conditions in decentralized systems shape the ways system leadership roles do or do not support a system's organizational effectiveness. The purpose of our study was to investigate the perspectives of Catholic school system leaders in order to examine how organizational conditions in these large decentralized systems of schools shape the system leadership roles diocesan superintendents have adopted. Research Methods: We conducted a qualitative analysis of data from 26 interviews with Catholic school superintendents leading a geographically diverse range of Catholic diocesan systems. Findings: We found superintendents believed the decentralized nature of their systems of schools required them to support the local reform efforts of individual schools within their portfolios rather than take on more active accountability and oversight responsibilities. Implications: These findings indicate the tendency for these system leaders to defer to local decision-making often came at the expense of these leaders’ maintaining consistent quality expectations across their systems. Ultimately, the analyses in this paper suggest the long term success of intentionally decentralized systems may rely on system leaders finding ways to counteract the tendencies identified by our participants.