The Sunnyside Independent School District Board of Education selected Dr. Juan Martinez (pseudonym) as its new superintendent of schools by an unusually cohesive 7-0 vote in 2002. In describing the superintendent search, the local paper characterized the board as highly politicized and often divisive. So the board's unanimity in appointing Juan to their most important position was surprising. Board members said Juan's knowledge of both academic and budget issues impressed them. Perhaps most important, according to at least one trustee, was Juan's promise to stay out of politics. Just over 2 years later, the board rejected an extension of Juan's 3-year contract by a 3-2 vote. Although the expressed reason was disappointing test scores, the paper reported that a majority of the board members were unhappy with Juan's leadership. Subsequently, the newspaper gave the board one of its weekly "Idiot Awards" for denying Martinez a contract extension, noting that he had made significant progress in dealing with parents and students and in stabilizing the district's finances, but recognizing that he had also, perhaps, disturbed the status quo by aggressively bringing accountability to bond projects and the like. What happened in just a little over 2 years that such a promising partnership went awry? What turned fiscal accountability, as described by the media, into a negative? What connections did a political scandal involving bribery and voting fraud have to do with Juan's abbreviated Sunnyside superintendency? This chapter tries to answer those questions and others, arguing that the "fit" between superintendent and district is a critical consideration from the very beginning, and suggesting that Juan's mistake may have been his choice to accept the Sunnyside position in the first place. ["The Importance of a 'Good Fit'" was written with Juan Martinez (a pseudonym).]