The purpose of this interpretive, multiple case qualitative study was to explore factors associated with presidential derailments in community colleges. The case studies involved interviews, document analysis, and observation. The population consisted of four community colleges in the United States. These distinctly different institutions produced the data for the investigation. The findings revealed five derailment themes among the four cases. These were: problems with interpersonal relationships, failure of the president to adapt to the institutional culture, difficulty working with key constituencies, failure to communicate, and a flawed search process. Two of the five themes from community colleges related directly to Leslie and Van Velsor’s (1996) derailment themes from the corporate sector. These were: problems with interpersonal relationships, and the inability to change or adapt to the culture of an organization during a transition (failure to adapt to the institutional culture). Finally, implications for preventing presidential derailments and for improvement in the presidential selection process are also presented.