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How do judges decide issues of equality? While prior scholarship demonstrates that judicial attributes such as partisan identification, gender, race, age, and career backgrounds help elucidate judicial decision-making, considerably less attention has been devoted to how judicial empathy may influence or condition judicial decision-making. Such scholarly attention is especially lacking in the study of courts outside of the United States. To bridge this critical gap, we examine how judicial empathy affects decision-making behavior by analyzing data from the Supreme Court of Canada from 1982 to 2015. We find compelling evidence that trailblazer women’s unique personal experiences exert a strong influence on judicial behavior within the Canadian Supreme Court. In fact, our findings demonstrate that the effects of judicial empathy extend across a broader array of discrimination cases in Canada compared to previous findings on the American courts. We find that trailblazer women have a greater propensity to vote in favor of discrimination claimants compared to their male peers. Normatively, these effects manifest as judicial empathy in discrimination cases where trailblazers themselves likely faced upward mobility challenges.