Life After Politics with Former Alderman Roberto Maldonado

Life After Politics

Life After Politics with Roberto Maldonado offers an exclusive, behind-the-scenes look at local government. Hosted by former Alderman Roberto Maldonado, each episode features candid conversations with former colleagues and political insiders, revealing the untold stories and hidden truths of city council. From legislative battles to the real impact of policy decisions, Life After Politics pulls back the curtain on how government really works—straight from those who’ve lived it.

  1. Jan 9

    EP 13 - Joe Moore

    In this episode, Former Alderman Roberto Maldonado sits down with former 49th Ward Alderman Joe Moore to reflect on his time serving one of Chicago's most diverse wards. Joe shares insights on how he balanced market-rate and affordable housing to maintain a diverse community, and the strategies he used to tackle public safety challenges during his tenure. The conversation also dives into the current political climate, offering a candid look at the shifts in Chicago politics over the years.

  2. Jan 9

    EP 12 - Sophia King

    In this episode, Former Alderman Roberto Maldonado sits down with former 4th Ward Alderman Sophia King to discuss her journey into politics and her time in office. Sophia opens up about the challenges she faced while serving one of Chicago's most dynamic wards, including her efforts to bring affordable housing to the community. She s9i. hares the obstacles she encountered while advocating for change, as well as the pivotal moments during her mayoral run that led her to step down from her aldermanic position. Sophia also reflects on her ongoing commitment to public service, working with Harriet's Daughters and continuing to make a positive impact in Chicago. Tune in for a conversation on leadership, resilience, and the drive to create lasting change in the city.

  3. Jan 9

    EP 11 - Luis Gutiérrez

    In this episode of Life After Politics, we sit down with former 26th Ward Alderman and U.S. Congressman Luis Gutiérrez to explore the pivotal moments that shaped his path into public service. Before politics, Luis lived a quiet life until a knock at his front door changed everything. He shares how that moment sparked his journey into local government, eventually leading him to Congress. Luis reflects on his time as an alderman, what motivated hime to step down and run for Congress, and how he continues to stand with people even after leaving office. Tune in for an inspiring conversation about purpose, community, and the power of staying true to your roots.

  4. Jan 9

    EP 10 - Jesse Granato

    In this episode of Life After Politics, we talk with Jess Granato, former alderman of Chicago's 1st Ward, as he shares his story, from his early life and upbringing to what first drew him into the world of politics. Jesse walks us through how volunteering led him to run for office, gives us a glimpse into his political views, and reflects on his experience during his time as alderman. He also opens up about life after politics and what he focused on today in his personal and professional journey.

  5. Jan 9

    EP 9 - Raymond A. Figueroa

    In this episode, former Alderman Raymond A. Figueroa joins us to share why he chose not to seek re-election after his first term, offering an honest look at his experience in office and his perspective on today's political landscape. He reflects on the challenges of staying true to his values in public service and talks about the meaningful work he continues to do outside of politics, standing with the people and pushing for real change in his community.

  6. Jan 9

    EP 8 - Milly Santiago

    In this episode of Life After Politics, former Alderman Roberto Maldonado sits down with former 31st Ward Alderwoman Milly Santiago for a powerful and personal conversation. Milly opens up about her journey into politics, the challenges she faced as a woman and Latina candidate, and the resilience it took to serve her community. From the struggles that led her to run, to the hurdles during her time in office and her second campaign-this episode is a raw and inspiring look into the realities of public service.

  7. Jan 9

    EP 7 - Leslie Hairston

    In this episode, former Alderman Roberto Maldonado welcomes former 5th Ward Alderman Leslie Hairston for a powerful conversation on leadership, resilience and public service. Hairston reflects on her journey into politics and the challenges she face throughout her time in office. Together, Maldonado and Hairston share the unique obstacles they encountered while serving different wards and the distinct approaches they used to lead and support their communities. This episode offers an honest, behind-the-scenes look at the complexities of local leadership and the dedication it takes to serve.

  8. 02/07/2025

    EP 6 - James Cappleman

    In Episode 6 ofLife After Politics, Roberto Maldonado sits down with James Cappleman, former Alderman of Chicago’s 46th Ward, for an in-depth conversation about his unlikely path into politics. James reflects on his early hesitations about a political career and how his diverse background in teaching, social work, and ministry shaped his perspective. He shares the pivotal moments that led him to view government as a vital platform to create meaningful change in his community. With personal stories and valuable insights, this episode offers a unique look at the intersection of service, faith, and public leadership.

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About

Life After Politics with Roberto Maldonado offers an exclusive, behind-the-scenes look at local government. Hosted by former Alderman Roberto Maldonado, each episode features candid conversations with former colleagues and political insiders, revealing the untold stories and hidden truths of city council. From legislative battles to the real impact of policy decisions, Life After Politics pulls back the curtain on how government really works—straight from those who’ve lived it.

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