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.

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.

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.

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.

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.

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.