In 2015, Dr. Jen Welter became the first woman to coach in the National Football League (NFL). Other female coaches followed. Yet, sports-studies scholars know little about the media’s response to these football pioneers. This paper presents critical themes on how popular media discussed female coaches by analyzing the hiring announcements of four women who coach or have coached in the NFL. Utilizing a critical feminist lens, this paper demonstrates that media outlets reproduced conventional media tropes by reassuring readers that women have the requisite knowledge, trivializing women’s achievements, underscoring the need for male player support, emphasizing appearance, and permitting sexist comments. However, it is evident that online publishers are simultaneously making progress. In most cases, the articles represented the coaches in ways that differ from how female athletes have been historically depicted. This research reveals nonlinear and incremental progress toward gender equality in football.