Despite promotion by well-known economists and supporting economic theory, econometric analyses of voucher systems often find that they have been unsuccessful in improving traditional measures of educational success. This paper examines a possible explanation of this phenomenon by comparing the drivers of educational achievement and of school popularity by examining private school choice. The findings of this paper indicate that there is a disconnect between school success and school popularity, which adversely effects both the demand and supply-side benefits of voucher systems. Additionally, this paper reviews matching mechanisms that seek to efficiently match students with schools based on both student and school preferences.