The Chicago Public School system recently enacted a merit pay program that awards bonuses to principals of up to $20,000 if their schools achieve certain goals related mostly to growth in student achievement (i.e., value added). A merit pay system can affect principal effort, the desirability of working in particular schools due to perceived differences in the probability of winning an award, and over the longer-term the skill distribution of the principal applicant pool. In this paper I explore the first two shorter-term dimensions using administrative data on students and school personnel in the Chicago Public Schools in combination with personnel information from other Illinois public school districts. I begin by describing the characteristics of award winners and their schools and compare them to non-winners. Next, I look at the effects of various measures of school performance and award receipt on subsequent job transitions using regression discontinuity design specifications. The regression discontinuity estimates will provide causal effects of award receipt on the probability of specific transitions, while the coefficients on the continuous measures of school performance illustrate the correlations between specific outcomes and principal transitions. The final component of the analysis examines the effect of the merit pay program on the distribution of principal quality using interrupted time-series approaches. Specifically, it will identify changes in the character of principal transitions following the enactment of the merit pay program as deviations from prior trends.