The purpose of the study was to examine the failed bond attempt of the Community School District and investigate reasons for the failure. Specifically, the role of the superintendent, the opposition, the media, and the school board during the bond election process were examined to determine how their roles influenced the outcome of the election. This qualitative case study employed purposeful sampling. Data collection techniques included document analysis, audiovisual material analysis, and personal interviews. Participants included media representatives, community members who were opposed to the bond election, members of the bond election committee, members of the board of trustees at the time of the election, and the district superintendent. Findings of the study included a description of how the superintendent’s work prior to the election and his role as spokesperson during the election contributed to its failure. In addition, the efforts of organized opposition had a significantly negative impact on the outcome of the election. The bond opposition used the media to create controversy strong enough to overpower what proved to be positive media relations. Finally, school board support must be unanimous and strong enough that board members are willing to work publicly in support of the bond election. Recommendations include: (a) The superintendent must conduct a needs assessment that includes the opinions of the community, (b) committee membership must be representative of the community, (c) the superintendent must not be the primary spokesperson for the bond election, (d) the community must be involved in the formulation and support of the bond proposal, (e) key members of the community must be willing to publicly support the bond election, (f) committees created to support and promote the election must be publicly active, (g) exercise caution as controversy can be created in the media that will overpower positive support, (h) respond positively to negative media as failure to respond to negative publicity can leave voters in a cloud of doubt, (i) members of the school board must publicly support a bond election, and (j) efforts by bond election supporters must be stronger than those opposing it.