Sherwin returns to the conversation on sundown towns—uncovering more of America’s hidden racial history. In this follow-up episode, he dives deeper into the policies, people, and systems that allowed these all-white communities to exist and, in many ways, still influence the present.

Sherwin sits down with Wisconsin State Senator Dora Drake for an in-depth conversation about the Wisconsin Black Legislative Caucus Tour

Sherwin dives into the controversial topic of language expectations for Uber drivers in the United States. Should drivers be required to speak American English fluently to ensure rider safety, communication, and service quality? Or does such a requirement cross the line into cultural bias and discrimination? Sherwin shares personal stories, highlights real rider experiences, and explores the balance between inclusivity and practicality in the gig economy.

Sherwin takes listeners into the heart of Washington, D.C. to break down the presence and purpose of security checkpoints throughout the city. From political protests to presidential motorcades, what are these checkpoints really for—and how do they impact the everyday lives of residents, commuters, and visitors?

Sherwin confronts escalating concerns that former President Trump may be undermining U.S. elections—not just for the 2026 midterms, but also to pave the way for future gains.

Sherwin breaks down how Donald Trump's political influence and GOP strategies are impacting Black representation in Texas. From redistricting to voter suppression tactics, Sherwin exposes the calculated moves that threaten to dilute Black political power in one of the nation’s most pivotal states.

Sherwin dives into the world of pre-wedding parties, unpacking the cultural, social, and even emotional differences between bachelor and bachelorette parties. From wild Vegas nights to wellness retreats and everything in between, Sherwin explores how gender roles, expectations, and personal style shape these iconic celebrations.

Sherwin pulls back the curtain on the troubling legacy of early U.S. presidents—many of whom were slave owners—who laid the foundation for executive power while upholding systems of human bondage. He draws a direct line from that era to today's political landscape, arguing that while slavery has been abolished, the mindset of control, inequality, and unchecked executive authority still persists—just in more subtle, systemic forms.

Sherwin dives into the growing trend of back-to-school drives—from backpacks and pencils to sneakers and laptops. Why are there so many of them? Who really benefits? And what does it say about our education system when schools rely on public donations just to get started each year?

Sherwin breaks down the 10 worst-performing school districts in the United States—looking at what went wrong, how students are affected, and the systemic failures that keep these districts trapped in cycles of underperformance.