Now a free man, Herbert returns to the scene of his crime, reflecting on accountability and his unresolved desire to apologize. The episode confronts the uncertain possible futures of those impacted by the habitual offender statute. Finally, Herbert invites a special guest into the radio studio, highlighting the intergenerational impacts of the criminal-legal system right alongside a hope for the future.
This episode features Victims Services Facilitator Cynthia Randall; Colorado State Senator Cleave Simpson; Daniel Loehr, CUNY School of Law; Adriana Vance, Habitually Screwed, Inc; Colorado State Representative Javier Mabrey; Colorado State Senator Julie Gonzales; Dan Meyer, Spero Justice Center; and Karter Alexander, Herbert’s son.
HABITUAL is a production of Colorado Radio for Justice.
Executive Producers: Herbert Alexander and Ryan Conarro
Hosts and Producers: Herbert Alexander, Ryan Conarro, and Seth Ready
Lead Writer: Ryan Conarro
Editors: Ringo Joon, Lucy Richardson, Herbert Alexander, & Ryan Conarro
Music composition: Xavier Gauthier
Mastering Engineer: Tongjai Lee
Graphic design: Mayela Cardenas
Vocal Coach: Mare Trevathan
Production of HABITUAL was supported in part by Colorado Media Project, a funding collective fiscally sponsored by Rose Community Foundation. HABITUAL was also supported in part by a grant from the University of Denver Prison Arts Initiative. Special thanks to Spero Justice Center and to Chuck Murphy, Investigative Editor at Colorado Public Radio.
HABITUAL is an original documentary podcast. This series includes limited excerpts of third-party media, such as news reporting and archival materials, used solely for purposes of journalism, commentary, and public interest analysis. These excerpts are selected carefully, used sparingly, and presented with additional reporting, context, and critique.
Any such material is incorporated in a transformative manner and only to the extent necessary to support factual storytelling, including the examination of legal systems, media narratives, and the lived experience of those directly affected.
HABITUAL relies on fair use as defined under 17 U.S.C. § 107 of U.S. copyright law. All rights to third-party materials, including news and media content, remain with their respective owners.
This episode includes the following sources:
© 2026 Colorado Radio for Justice - HABITUAL
All Rights Reserved
What is HABITUAL?
HABITUAL is a podcast from Colorado Radio for Justice - told by someone who survived it. Herbert Alexander served 14 years in Colorado prisons, labeled a "habitual offender" under the state's three-strikes law, which can increase sentences exponentially even for nonviolent crimes. Against all odds, Herbert got himself free. Now, he's telling his story, and he's investigating habitual statutes across the United States that fuel mass incarceration and alter the lives of thousands of people.
HABITUAL traces the history, power, and consequences of habitual statutes through Herbert’s deeply personal story. Alongside co-hosts Seth Ready and Ryan Conarro, Herbert interviews his mother, his wife, and his son. He returns to the scene of his final crime. And he sits down with lawmakers, historians, victims and their advocates, and families who live with the lasting impacts of the law. Along the way, he stumbles upon the shocking, dark origin story of the law across 49 states. It all adds up to a deep interrogation of how habitual laws expand prosecutorial power, pressure plea bargains, and transform prison terms into life-defining punishments, without consideration of rehabilitation, accountability, or repair.
HABITUAL is the story of one man’s past, present, and future. And it’s a sweeping tale of power, punishment, and people across the country fighting for the possibility of change against all odds.