In Chicago's politics, the old adage still fits — 'We don't want nobody, that nobody sent!' Who Sent Ya? is a podcast from The Urban Center bringing you the political insider perspective straight from the people shaping Chicago. Understand the why and the how we got here. Subscribe and tune in to weekly episodes. Who Sent Ya? Chicago, politics and more.
Prior to one of the most important and historic elections, the Urban Center's Juan Rangel and Bobby Sylvester discuss what is at stake as Chicago elects its first fully independent school board. The questions are: Will the school board become independent of City Hall? Will they be beholden to the Chicago Teachers Union? Or will the people's voice be heard? This November 3rd, it is up to you!
22 Oct 2026
Who Sent Ya? w/Special Guest Maze Jackson
On this podcast episode, we talk with the incomparable political commentator, Maze Jackson. Join us in a candid conversation about Black empowerment in Chicago, the shifting power dynamics with Brandon Johnson, the elusive Black/Brown coalition, and What’s in it for the Black people? Tune in.
15 Oct 2026
Victor Reyes: Who Really Runs Chicago Now?
Chicago political veteran Victor Reyes joins Bobby Sylvester and Juan Rangel to kick off Season Two of Who Sent Ya?From the Daley and Rahm years to today’s political landscape, they explore who still matters, the rise of progressive organizations, the changing influence of Latino leaders, and what it takes to turn political power into effective government. A conversation about how Chicago works, and where it goes next.
1 Sept 2026
How Illinois Politics Works Now: Frank Calabrese on Power, Money, and Organization
Political strategist Frank Calabrese explains the forces reshaping Illinois politics: the strength of political organizations, the limits of big-money spending, the changing progressive movement, and why disciplined campaigns still matter in Chicago and beyond.
25 Aug 2026
From the Last of the Blue Dogs: A Warning for the Democratic Party
One of the last of a dying breed, “blue-dog” Democrat, former IL Congressman Daniel Lipinski joins our Who Sent Ya? podcast to issue a warning as the Democratic Party steers hard left toward Socialist territory. Tune in.
18 Aug 2026
21 Seats. One Election. The Fight for Chicago’s Schools
For the first time, Chicago voters will elect all 21 members of the Chicago Board of Education. But the fight over who controls the city’s schools has been decades in the making.Juan Rangel and Bobby Sylvester trace the path from local school councils and mayoral control to the rise of the Chicago Teachers Union as a political force. They break down why the elected school board was created, how CTU’s influence changed the balance of power, and why the November 2026 election could determine the direction of Chicago Public Schools for years to come.
11 Aug 2026
Silvana Tabares: More Police. Smarter Spending. Better Government
Ald. Silvana Tabares joins Who Sent Ya? for a candid conversation about the political battle lines taking shape across Chicago: more police or fewer, bigger government or smarter spending, ideology or basic services. From growing pushback against Mayor Brandon Johnson to fights over public safety, CPU, city spending and taxes, the conversation gets at a bigger question facing Chicago: what kind of city government do voters want next?
4 Aug 2026
Chicago’s Elected School Board: A springboard to power
For the first time in Chicago history, voters will elect an entire school board to guide and direct the future of its students. In the next podcast episode of “Who sent ya? Chicago, Politics and more, learn how the obscure elected school board position has become the springboard to power in Chicago.
28 Jul 2026
The Rise of the Extremists Pt 2
Chicago is a sports town that plays hard to win. That includes its politics, known as a “blood sport,” where interests jostle for power. Tune in to our next podcast episode of “Who Sent ya? Chicago, Politics and more”, The Rise of the Extremists, Part 2, as we breakdown the power of Chicago’s new political machine led by the Chicago Teachers Union.
29 Jun 2026
The Rise of the Extremists: Part 1
With the demise of Chicago’s historic Democratic political machine, how did we end up with its powerful successor, a Socialist syndicate led by, of all interest groups, the Chicago Teachers Union. Tune in to our next podcast episode of “Who Sent ya? Chicago, Politics and more”, The Rise of the Extremists, Part 1.
17 Apr 2026
Who Sent Ya? - INTRO EPISODE
In Chicago's politics, the old adage still fits — 'We don't want nobody, that nobody sent!' Who Sent Ya? is a podcast from The Urban Center bringing you the political insider perspective straight from the people shaping Chicago. Understand the why and the how we got here. Subscribe and tune in to weekly episodes. Who Sent Ya? Chicago, politics and more.
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