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Immigrants, advocates, and policymakers believe—and a growing body of empirical research generally confirms—that legal representation is associated with favorable legal outcomes in immigration courts. But do lawyers matter more for certain immigration judges than others? If so, which judge characteristics moderate the effect of legal representation on case outcomes? Likewise, do lawyers matter more in certain decisional environments than others? We address these timely questions of both theoretical and policy importance by analyzing 1,831,639 removal proceedings that were decided by 608 immigration judges between 1998 and 2019. We find that the effect of legal representation in reducing the probability of removal is larger for female judges than male judges. In addition, the effect of legal representation increases as the number of years on the bench increases. We also find that legal representation has a larger effect for removal proceedings that were (a) completed during Democratic presidential administrations, (b) adjudicated in immigration courts in the Ninth Circuit Court of Appeals, and (c) when caseloads for judges are increasing.