Through a comparative analysis of the media coverage and legal treatment of a national sample of criminal cases involving sexual contact between teachers and their adolescent students, this research examines how gender and racial inequalities are reproduced and resisted in the news media and criminal justice system. Using regression analysis of sentencing outcomes, I find support for the selective chivalry hypothesis, which suggests that female defendants who adhere to dominant gender expectations experience leniency in the criminal justice system while female defendants who are viewed as gender deviants are treated especially punitively. I also employ qualitative discourse analysis of the new media coverage and court room construction of a subsample of 66 cases to consider how inequality is reproduced and resisted. I draw on a conceptualization of hegemonic ideology as a set of symbolic resources that individuals have differential access to depending on their location in the matrix of privilege and oppression. Using this conceptualization, I elaborate how defense attorneys strategically draw on patriarchal views of women's passivity to reduce the culpability of their female clients, how prosecuting attorneys resist these hegemonic ideals and demand that the sexual perpetrating of both male and female defendants be taken seriously, and how judges discursively perform neutrality even while making sentencing decisions that are shaped by gender ideology. I also analyze the media framing of these cases, including how the explosion of discourse around cases involving white female perpetrators relates to the regulation of female sexuality and how the politics of Black respectability are used to frame cases involving Black male defendants. Finally, I analyze the constructed and contested nature of sexual victimhood, and how the differential access to claims of "worthy victimhood" identity relates to the race and gender of the adolescent victim.