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.
Former Alderman Joe Moore discusses balancing diverse housing and tackling public safety challenges with Roberto Maldonado, offering insights into Chicago's evolving political landscape in this interview.
9 Jan 2026
EP 12 - Sophia King
Former Alderman Roberto Maldonado interviews Sophia King about her political journey, the challenges of serving Chicago's 4th Ward, and her ongoing commitment to public service.
9 Jan 2026
EP 11 - Luis Gutiérrez
Host Roberto Maldonado interviews former Congressman Luis Gutiérrez, who recounts the life-altering moment that propelled him into public service and discusses his motivations for serving his community.
9 Jan 2026
EP 10 - Jesse Granato
Former alderman Jesse Granato recounts his journey into Chicago politics, reflecting on his experiences and revealing his focus in his personal and professional life after leaving office in an interview with Roberto Maldonado.
9 Jan 2026
EP 9 - Raymond A. Figueroa
Raymond A. Figueroa discusses his decision to leave politics after one term as alderman, reflecting on the difficulties of upholding his values while in office in an interview with Roberto Maldonado.
9 Jan 2026
EP 8 - Milly Santiago
Former Alderman Roberto Maldonado interviews former Alderwoman Milly Santiago, who shares her experiences as a Latina woman in politics and the challenges she overcame while serving her community.
9 Jan 2026
EP 7 - Leslie Hairston
Former Alderman Leslie Hairston discusses leadership and public service with Roberto Maldonado, highlighting challenges faced and approaches used to support communities in this interview.
7 Feb 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.
1 Feb 2025
EP 5 - Roderick 'Rod' Sawyer
In Episode 5 of Life After Politics, Roberto Maldonado sits down with his former colleague, Rod Sawyer, the former Alderman of Chicago’s 6th Ward, for a gripping conversation. They delve into their first eye-opening experiences with government, pull back the curtain on the messy world of city bureaucracy, and tackle the urgent issue of gentrification – a force rapidly reshaping Chicago in ways no one expected. This is a must-listen for anyone curious about the real challenges behind the city's changing landscape.
25 Jan 2025
EP 4 - Tom Tunney
In Episode 4 of Life After Politics, former Alderman Roberto Maldonado sits down with Tom Tunney, former Alderman of the 44th Ward to reflect on his remarkable journey from businessman to trailblazing public servant. As the first openly gay alderman in Chicago’s history, Tunney shares insights into the impact he made in City Council and the highlights of his career, offering a candid look at his legacy and the challenges he faced along the way. Tune in for this episode's riveting conversation on leadership, change, and progress.
30 Dec 2024
EP 3 - Billy Ocasio
In Episode 3 of Life After Politics, Roberto Maldonado sits down with his close friend, and predecessor, former Alderman of the 26th Ward, Billy Ocasio, as they relive some of the heated debates over the Don Pedro Statue, to navigating the political landscape under the Daley's administration. Offering a rare and personal glimpse into the power plays, challenges, and triumphs that had shaped both of their respective careers.
14 Dec 2024
EP 2 - Rey Colón
In Episode 2 of Life After Politics, Roberto Maldonado sits down with his former colleague, Alderman Rey Colón, for an in-depth conversation about the origins of their political careers and the pivotal moments that defined their time in office. They reflect on the challenges and victories that shaped their Aldermanic tenures, while also diving into the complex and often contentious issue of gentrification in their respective wards. With firsthand stories and candid insights, Maldonado and Colón explore how urban development reshaped their communities—and the hard choices they had to make along the way. Don’t miss this compelling discussion of politics, progress, and the changing face of Chicago.
6 Dec 2024
EP 1 - Proco "Joe" Moreno
In the first episode of Life After Politics, former Alderman Roberto Maldonado sits down with his former colleague, ex-Alderman Proco "Joe" Moreno, to reflect on their time in Chicago's City Council. They share candid insights into their early perceptions of the council and how those views shifted over time, revealing the challenges and complexities of local politics. The conversation also dives into their personal journeys after leaving office, offering an inside look at the evolving political landscape. The episode closes with a compelling discussion on the upcoming 2024 presidential election, where both guests offer their perspectives on the national political scene and its impact on local governance.
Who has been a guest on Life After Politics w/ Roberto Maldonado
Names identified in recent episode analyses. Showing up to five guests.
Joe Moore
Sophia King
Luis Gutiérrez
Jesse Granato
Raymond A Figueroa
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
2 ratings
Podcast Authority Score: 14 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
28
Social presence
0
YouTube
0
Engagement
0
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