How statistics are wielded and presented in the real world cannot be separated from the fact that social issues operate within systems of marginalization, privilege, and power. Thus, statistical literacy necessitates the application of a true critical lens. Continued calls for critical statistical literacy from a consumer orientation within K-16 education, points to the need for research on how critical statistical literacy is enacted, particularly among the population of preservice mathematics teachers responsible for answering such calls. This study employed case study methodologies to gain deeper insight into how secondary preservice mathematics teachers enact Critical Statistical Literacy Habits of Mind (CSLHM) when making sense of data representations from the media. Critical Statistical Literacy Habits of Mind (CSLHM) are the thinking behaviors called upon to make sense of statistical messages with a specific focus on how the statistics and/or statistical message are used to uphold or dismantle structures of inequity. Findings reveal that preservice teachers emergently enact CSLHM. Some preservice teachers enact particular CSLHM robustly, although not habitually. Broader implications include the need to support preservice teachers’ development of CSLHM so that they can support their students to do the same.