The purpose of this study was to determine if there was a correlation between the leadership style of the school principal and student academic achievement. This study was focused on high school administrators in New York State. In this case the assessment of student performance was based on the New York State Comprehensive English Regents Exam (CERE) which is administered at the end of the eleventh grade year. This study was set up with a descriptive research design using a descriptive survey technique with two survey tools (Campbell & Stanley, 1963; Mason & Bramble, 1989). The unit of study was a single high school in New York State with a configuration of grades nine to twelve and a principal who had been in place for three or more years as of the time of the administration of the 2005 CERE. Department chairs or teacher leaders from each school were asked to complete an online version of the Multifactor Leadership Questionnaire Rater Form (MLQ 5X) to assess the leadership behaviors of his/her principal. There were four research questions and ten ancillary questions considered during this study. Of the four research questions there were three that yielded results that may indicate a connection between the use of transformational leadership style and respondent satisfaction, their willingness to give extra effort, and their characterization of their principal’s effectiveness. In the case of the ancillary questions only question seven yielded a possible connection between the length of time in education of principals of high performing schools and those in low performing schools.