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This paper examines the strategies of challengers and the choices of voters to answer a vitally important question about elections to the states ’ highest courts: does the quality of challengers have a significant impact on the electoral successes of incumbents. In other words, do challengers with experience on the bench, and thus the ability to represent qualified alternatives to incumbents, reduce incumbents ’ vote shares, other things being equal. From a different perspective, we evaluate whether the electorate seemingly has the ability to make candidate-based evaluations by distinguishing qualified from unqualified challengers. To address these questions, we examine all 208 elections to the states ’ highest courts from 1990 through 2000 in the twenty-one states using partisan or nonpartisan elections to staff their benches. Using a Heckman two-stage estimation procedure that takes into account factors influencing challengers’ decisions to run as well as factors affecting the electorate’s choices among candidates, we find that quality does matter. Experienced challengers significantly lessen the electoral security of incumbents, and the electorate appears to have the ability to evaluate challengers ’ qualifications. These findings suggest a broader need to rethink traditional notions that the electorate i