In this deeply personal and unapologetically raw episode, Sherwin opens up about the exact moment he hit his tipping point with Donald Trump. From years of political chaos to rising legal controversies, the final straw came when Sherwin realized — Trump’s not just bending the law, he’s taking it into his own hands.

Sherwin breaks the explosive story shaking Milwaukee’s legal scene: a sitting court judge arrested by the FBI for allegedly helping an illegal immigrant avoid ICE. With obstruction charges on the table and the justice system under the microscope, Sherwin dives into the details, the drama, and the deeper implications.

In this no-holds-barred episode, Sherwin dives deep into Michelle Obama’s recent podcast appearance where she boldly opens up about life behind the scenes — from marital struggles to White House drama.

Sherwin takes the gloves off to dissect the dynamics behind these iconic couples, questioning the cost of loyalty, image, and emotional labor in relationships where the wives seem to be rewriting the rules. Is it strength or sabotage? Support or spotlight-stealing? Sherwin breaks it all down with raw honesty and sharp insight. Tune in for truth bombs, real talk, and a whole lot of perspective.

Tired of masks, mind games, and mixed signals? Sherwin gets real about the ways some women manipulate men—using attention, affection, and emotional bait to control the narrative. But this podcast isn’t just about calling out the chaos—it’s about breaking free from it. No More Games is a space for men who are done chasing validation and ready to surround themselves with people who actually value their presence. Each episode is part wake-up call, part healing session. Because life’s too short to beg for what should be freely given: respect, time, and real connection.

Sherwin pulls no punches in this raw, reflective podcast exploring the reality behind unhappy marriages—and why staying single might just be the smartest love story of all. From societal pressure to personal freedom, each episode unpacks stories of people who feel trapped, tied down, or just plain tired of the marital myth. Whether you’re single by choice or circumstance, Better Alone is your weekly reminder that peace of mind beats a broken heart every time.

It’s the last hour of the show, and Sherwin’s letting it breathe. No script, no filter — just a straight talk session covering whatever’s on his mind. From politics and pop culture to local headlines, internet foolishness, and whatever’s happening in the group chat, this is Sherwin in full form. Smart, sharp, and sometimes spicy, it’s the kind of hour that keeps you nodding, laughing, and maybe even yelling back at your speakers.

Sherwin calls out the language that too many adults use to describe boys — especially Black boys — as “young men” or “young adults” when they’re still just kids. He unpacks how this seemingly small shift in language feeds into dangerous narratives, strips children of their innocence, and contributes to harsher treatment in schools, the media, and the justice system.

In this episode of Case Files: Milwaukee, Sherwin reads and analyzes a newly filed criminal complaint involving a local Milwaukee school teacher accused of sexual misconduct. With careful attention to detail and sensitivity, Sherwin walks listeners through the allegations, legal language, and broader implications of the case. This is a factual, unflinching look at a troubling situation in our community.

Content warning: This episode discusses allegations of sexual misconduct and may not be suitable for all listeners.

Sherwin talks about white supremacy, Kanye West's relationship with his cousin, what the world was per all this technology and material possessions.