The language used by US courtroom actors in criminal trials has long been studied for biases. However, systematic studies for bias in high-stakes court trials have been difficult, due to the nuanced nature of bias and the legal expertise required. New large language models offer the possibility to automate annotation, saving time and cost. But validating these approaches requires both high quantitative performance as well as an understanding of how automated methods fit in existing workflows, and what they really offer. In this paper we present a case study of adding an automated system to a complex and high-stakes problem: identifying gender-biased language in US capital trials for women defendants. Our team of experienced death-penalty lawyers and NLP technologists pursued a three-phase study: first annotating manually, then training and evaluating computational models, and finally comparing human annotations to model predictions. Unlike many typical NLP tasks, annotating for gender bias in months-long capital trials was a complicated task that involves with many individual judgment calls. In contrast to standard arguments for automation that are based on efficiency and scalability, legal experts found the computational models most useful in challenging their personal bias in annotation and providing opportunities to refine and build consensus on rules for annotation. This suggests that seeking to replace experts with computational models is both unrealistic and undesirable. Rather, computational models offer valuable opportunities to assist the legal experts in annotation-based studies.