Judges and judicial systems have become more specialized in response to increasing legal complexity. While the theoretical literature has discussed judicial specialization extensively, deliberating its pros and cons and its implications—arguably an appealing background for empirical investigation—few empirical studies have attempted to quantify the relationship between judicial specialization and case outcomes. This Article fills that lacuna. It analyzes a hand-coded dataset of tax cases in which rulings were made by both specialized tax judges and generalist judges in Israeli District Courts. Its main finding is that specialized tax judges are more inclined than generalist judges toward the Tax Authority. It also finds that women judges and judges who worked in the private sector before their nomination are more inclined toward the Tax Authority than men judges and judges who were part of the public sector before taking the bench.