Background: Massive retirements, increased expectations, and mounting political pressures have resulted in a diminished talent pool for school superintendents. For school boards of the 124 school districts on Long Island, New York, the selection of a superintendent has been further complicated by sky-rocketing taxes and scandals leading to an erosion of trust. To address an increasing number of superintendent vacancies in this region, the majority of local boards hire search consultants. Purpose: This study examines, compares, and assesses the search consultants' process in securing superintendent candidates on Long Island within the social, political, and economic context existing in 1995 and 2005 to determine similarities and differences within the decade. Research Design: For this qualitative case study, search consultants serving Long Island were identified, and in-depth interviews were conducted, tape-recorded, transcribed, and analyzed with coding formulated based on emerging themes. Findings: Long Island boards select predominately retired local superintendents as search consultants and prefer experienced neighboring superintendents to fill vacancies. Consultants rely on outreach for recruitment of candidates, recommend "silent searches," facilitate school community stakeholders' participation in construction of a candidate's profile, endorse criminal and credit checks, and serve to neutralize negativity toward and/or between board members. Through succession planning, more women are assuming superintendencies; there is no gain for people of color. Conclusions: Mandatory board training targeting effective group decision making and values clarification, use of data, mentoring and advocacy of underrepresentative aspirants, and succession planning appear advisable to attract a broader talent pool and increase diversity in the superintendency.