Governor Tony Evers has confirmed he won’t seek another term—and the political ripple effects are just beginning. In this episode, Sherwin breaks down what Evers' decision means for Wisconsin's future and why he’s urging Democrats to "get ahead of the ball" before a major legislative showdown, referred to as the “Big Beautiful Bill,” reshapes the state’s political landscape. What’s at stake? Who’s stepping up? And how will this moment define the direction of the Democratic Party in Wisconsin? Sherwin digs deep, asks bold questions, and lays out the path forward.

In this urgent episode, Sherwin breaks down the Milwaukee Common Council's decision to call an emergency meeting in response to the recent surge in violence gripping the downtown area. With rising concerns from residents, business owners, and city leaders alike, Sherwin examines the causes, the tension, and the proposed solutions on the table. What actions are being considered, and will they be enough to restore safety and confidence in the heart of the city? Tune in for a timely conversation on public safety, city policy, and the path forward for Milwaukee.

Sherwin’s got jokes—and a whole lot going on. In this off-the-rails episode, he laughs through the madness of a week that already feels like it’s been a month. From wild headlines to random tangents and a little organized chaos, nothing is off limits today. It’s only Tuesday...

In this thought-provoking episode, Sherwin jumps between headlines, hot takes, and a bit of humor—because why not? Along the way, he tackles a recurring debate: does music really influence people to do bad things? Sherwin firmly says no—music reflects life, it doesn’t cause it. From social issues to media narratives, he’s connecting the dots and calling out the myths. It's a little bit of everything, and a whole lot of real talk.

In this powerful and urgent episode, Sherwin dives into the chaos that unfolded this past weekend on Water Street in downtown Milwaukee. With disturbing scenes of violence, destruction, and community unrest, the city is left asking—how did it come to this? Sherwin and his producer break down the timeline of events, playing audio and video clips from the scene to bring listeners closer to the reality faced by residents, business owners, and local authorities. They also explore community reactions, law enforcement responses, and what this means for Milwaukee’s future.

In this deeply personal and urgent episode, Sherwin addresses the troubling rise in violence within Milwaukee’s Black community. With honesty and clarity, he explores the root causes—from generational poverty and systemic neglect to strained relationships with law enforcement and limited access to opportunity. Through compelling commentary and real voices from the streets, Sherwin challenges listeners to look beyond headlines and statistics. What’s really driving this violence? And more importantly, what can be done to change the trajectory?

In this eye-opening and emotionally charged episode, Sherwin shines a light on the staggering statistics surrounding children in Milwaukee’s foster care system—many of them Black, many of them labeled "troubled," and far too many of them aging out without ever finding a permanent home. With support from producer Rick, who cues up some heartbreaking data and firsthand accounts, the episode turns real when Rick asks Sherwin directly: “Would you ever adopt one of these kids?”

Sherwin’s unfiltered response—“Hell no!”—opens up a raw and honest conversation about fear, bias, responsibility, and the hard truth behind why so many kids remain unadopted.

Sherwin dives deep into the political landscape of Wisconsin as the race for governor heats up. With the current administration nearing the end of its term, speculation swirls around potential candidates from both major parties—and a few independents who might shake things up. Sherwin analyzes the rising stars, the returning veterans, and the policy issues that could define the next election. Will Wisconsin stay the course or shift direction? Tune in for informed insights, sharp commentary, and a glimpse at the state’s political future.

Sherwin is back with part two of his deep dive into Wisconsin’s political future. This time, he’s zeroing in on one name in particular: Milwaukee County Executive David Crowley. Could he be the fresh, unifying force Wisconsin needs? Sherwin lays out the case for Crowley as a potential gubernatorial contender—his leadership style, policy wins, and the energy he brings to the table. Plus, Sherwin unpacks the broader field of possible candidates and how Crowley might stand out in a crowded race. It's a passionate, thoughtful take you won’t want to miss.

In this unexpected detour from politics, Sherwin shares that he’s been summoned for jury duty—and he's not sure how he feels about it. Is it a civic duty, a pointless chore, or maybe a secret opportunity to see justice in action? Sherwin talks through the pros, the cons, and the excuses (real and imagined) running through his head. Tune in for a funny, honest reflection on responsibility, the justice system, and the universal feeling of getting that dreaded envelope in the mail.