The Kentucky Education Excellence Scholarship (KEES) is a merit-based scholarship program intended to increase college access, long-term academic commitment, and retention of top students within the state. KEES uses a heavily graduated award structure and both high school grade point average and standardized test scores to establish award amounts. Using school-level data, this study applied means tests, correlation, and multivariate analysis to examine the relationship between the demographic composition of high schools and the amount and number of KEES awards received. KEES was found to be regressive, and that regressivity is compounded by its graduated structure. Students from higher socioeconomic status schools, from schools with more Caucasian students, or from schools with more females received a higher proportion of KEES awards, in larger amounts, than those from other schools. The source of KEES funding was also found to be regressive: the more successful the program, the greater the strain on its static lottery revenue funding. Because awards are not indexed to inflation, their impact on college affordability diminishes as education costs rise. Recommended steps for addressing regressivity in the KEES program, including clearly defining the program's primary goal and introducing a need-based component, are discussed. (Contains 4 footnotes, 5 tables, and 1 figure.)