Representations of Black masculinity in popular culture remain a focal point of social science and cultural studies research. Yet, research shows that Black men are negatively portrayed in news stories. Therefore, when a series on Black men, conceived and carried out primarily by a Black journalistic team, was published in a national agenda-setting newspaper, The Washington Post, it was important to question if Black masculinity was represented in this same light or represented in other, more positive ways. The purpose of this research was to investigate whether the series succeeded in reshaping the image of Black men and to what extent it exhibited Jackson and Dangerfield’s five factors of Black masculine positionality. The study found that slightly more than 50 percent of the stories presented a counter-stereotype, showing complexity in Black men’s lives. However, some stories left Black men ‘voiceless on the sidelines’. The study illustrates the difficulties even a well-planned series can face when trying to break out of conventional reporting tendencies.