Detroiters Are Our Assignment Editors: Orlando Bailey on Truth, Power & Black Leadership

“Detroiters are our assignment editors.” That line from Orlando Bailey sets the tone for a conversation that is both legacy-rooted and forward-looking, as he sits back in the Detroit is Different studio and walks us through his evolution from a kid in Youth on the Edge of Greatness to Executive Director of Outlier Media—one of Detroit’s most trusted sources for civic truth. In this episode, Orlando reflects on growing up East Side under the watchful love of giants like Maggie DeSantis and Donna Givens Davidson, describing ECN as an organization that “walked right beside me my entire life.” He breaks down the weight of Black leadership today, especially in a media landscape where “the truth is incendiary to the chambers of power,” and shares how becoming an ED forced him to be “as open, as honest, and with as many eyes on my stuff as possible.” We talk collard green juice on the gym floor, judges who need robes, and why Detroit storytelling—done authentically—remains the strongest defense against erasure. With wisdom, humor, and Detroit cultural fluency, Orlando unpacks everything from the future of local journalism to the politics of public transit to the spiritual power of Black people telling the truth about themselves. This episode is Detroit past, Detroit present, and Detroit future talking to each other in real time.