In recent decades, visible unsheltered homelessness, and the street disorder that comes with it, have become both the background noise of life in urban America and perhaps the most frustratingly persistent and seemingly intractable problem facing blue cities. But how did we get to this point? For answers, journalist Emma Pettit joins us on BCB to talk about her fascinating, insightful, and sound-rich Reflector podcast documentary, Street Fight: How America Chose Homelessness, which offers a history of homelessness in America. (Reflector is the podcasting arm of Longview, a recently formed journalistic entity that focuses on providing explanatory history and context for hot-button public debates.) Over those episodes, Pettit dives deep into the question of how American cities arrived at today’s homelessness crisis – and whether the commitment of homelessness advocates in blue cities like New York and Los Angeles to protecting the autonomy of the homeless has sometimes undermined both care for vulnerable people and the public’s ability to freely access shared public spaces. Our conversation begins with Emma describing the origins of the homelessness problem in America, as rootless men in the late 19th and early 20th centuries -- “tramps” and “hobos” – rode the rails and traveled the country in pursuit of seasonal jobs. As time passed, this cohort would eventually settle in skid row neighborhoods of American cities, circumscribed islands of poverty, vice and relative permissiveness where they could find beds in flophouses and other cheap lodging. We discuss how writers, musicians, and adventurers helped romanticize vagrants’ mobility as a form of freedom, creating an image of homelessness very different from its modern incarnation. Emma then tells us how overlapping changes in the 1970s and 1980s, such as urban redevelopment and stricter housing standards, along with deinstitutionalization from psychiatric institutions and rising usage of hard drugs, remade the old, romanticized image of homelessness into something grimmer and more sinister. The population living outside became more diverse, and severe mental illness became more visible in public spaces. Pettit emphasizes to us the unintended consequences of well-intentioned reforms: eliminating degrading housing or abusive institutions did not produce better places for their former residents to live. Meanwhile, a new generation of homeless advocates began to emphasize the autonomy of homeless people in the face of urban authorities’ efforts to curtail their antisocial behaviors. We dissect the emblematic tale of Joyce Brown, a mentally ill woman living on a Manhattan sidewalk whose involuntary hospitalization sparked a major civil liberties battle in 1987. Pettit explains that the national debate then over what to do with Brown, which pitted NYC Mayor Ed Koch and Brown's own family against the ACLU and other advocates for her freedom, set the stage for present-day battles over how much autonomy to give to those living in crisis on urban streets. The discussion then turns to the rise of Housing First, predicated on offering permanent housing without requiring sobriety or treatment beforehand, alongside supportive services. These new ideas took root in the ’90s with bipartisan support and high hopes of ending chronic homelessness. Why those hopes went unfulfilled remains an ongoing topic of sharp disagreement, with conservative critics now questioning whether voluntary treatment sufficiently addresses severe addiction and mental illness, while supporters point to rising housing costs, inadequate funding, and programs that delivered “housing only” without the promised support. We close by looking at blind spots across the political spectrum. The left tends to minimize personal behavior and neighborhood harms or use language that obscures profound suffering, Pettit argues, while the right overestimates what punishment and involuntary commitment can accomplish while underplaying housing costs and shortages of treatment capacity. “People on the left, I think, tend to downplay the personal, mental illness or addiction or choice… On the right, I think that now there is this idea that only punishment and only involuntary commitment… that only bringing down the hammer will solve this problem,” Pettit says. But that binary obscures as much as it reveals: “I don’t even like saying both sides. I like saying all sides because… people’s thoughts about the stuff [are] always more complicated and more kaleidoscopic than we think that it is.” OUTSIDE SOURCES: Emma Pettit, "Street Fight Part I: Hobos, Bums, and the Homeless," Reflector, Sept. 9, 2026. Emma Pettit, "Street Fight Part II: Cruel & Unusual," Reflector, Sept. 17, 2026. Emma Pettit, "Street Fight Part III: Can We End It?," Reflector, Sept. 24, 2026.
