Life After Politics w/ Roberto Maldonado

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 c...

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...

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 refle...

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...

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...

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 tim...

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 dist...

In Episode 6 of Life 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...

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...

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...

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...

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 gent...

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...