29: Deep Dive on the Westside29: Deep Dive on the Westside
a Place for everyone
Beth Roalstad and Christy Milligan talk candidly about homelessness, shrinking safety nets, and dignity-first responses in Colorado Springs. The conversation highlights complex barriers, real-life stories of change, and practical ways community members can get involved.
30:24•2 Jul 2026
Housing, Humanity and Hard Truths on Colorado Springs’ Westside
Episode Overview
- Homelessness in Colorado Springs is complex and highly individual, so a wide range of different interventions is needed rather than one single solution.
- Westside CARES focuses on both prevention (rent, utilities, medical help) and remediation through housing navigation and on-site services in one location.
- Policy changes such as reduced Medicaid reimbursements and stricter camping and vehicle ordinances increase hardship for people already living on the margins.
- Permanent supportive housing can stabilise highly visible, high‑needs residents, but only if real support services are funded and sustained.
- Humanising people in poverty, recognising shared humanity, and engaging earnestly with local charities, books, and conversations are key ways residents can contribute.
“If we cared as much about people sleeping on our streets as we do about the price of gas, we could solve homelessness.”
How do people find strength in their journey to sobriety, housing stability, and dignity? This conversation in *A Place for Everyone* brings together two seasoned leaders who’ve spent decades walking alongside neighbours in crisis. Host Beth Roalstad chats with Christy Milligan, CEO of Westside CARES, about what homelessness and housing insecurity actually look like in Colorado Springs right now.
You’ll hear how Westside CARES grew from nine churches into a 25‑faith, 375‑volunteer operation serving around 10,000 people a year, with 85% of guests technically housed but one setback away from losing it all. Christy breaks down the mix of prevention help, like rental and utility support, and on‑the‑ground housing navigation for people who are newly or chronically homeless.
She explains why having many different interventions matters, because, as she puts it, homelessness is “comprised of human beings…with unique stories, unique histories that began long before the day they became homeless.” The two tackle tough policy shifts too: shrinking Medicaid reimbursements, stricter public benefits, and local ordinances that punish people living in vehicles.
Christy’s blunt line, “If we cared as much about people sleeping on our streets as we do about the price of gas, we could solve homelessness,” sums up the tone: honest, a bit wry, and deeply human. You’ll also hear about moral injury in healthcare, the strain on small providers, and why permanent supportive housing needs real support services attached.
Beth and Christy share moving stories of people whose health, mood, and relationships changed once they had a safe door to lock. For anyone curious about what’s really happening with homelessness, why some people fall through every crack, and how ordinary residents can help, this episode offers straight-talking clarity and a reminder that, as Christy says, “we are all in this together.” It might just leave you asking: what small step could you take to stand with your unhoused neighbours?
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