In this episode of Caviar & Criminals, Dana takes Anthony back to the glittering chaos of the 1893 Chicago World’s Fair — a moment in American history that promised innovation, progress, and possibility. But just a few blocks away from the White City’s shining lights, something far darker was unfolding.

This is the story of charm weaponized.

Of a man who could sell you a dream, a job, a marriage proposal… and then make you disappear.

Dana walks Anthony through the twisted life of H.H. Holmes — the man often called America’s first serial killer — from his early days of scams and insurance fraud to the construction of his infamous “Murder Castle.” Hidden rooms. Sealed vaults. Gas lines. A hotel built not just for guests, but for control.

And then there’s the question that still lingers: how much of the legend is true… and how much was manufactured by a press hungry for horror?

Anthony reacts in real time as Dana unpacks the psychology, the manipulation, the financial grifts, and the cultural panic that turned Holmes into a monster of mythic proportions. Along the way, they explore the blurred line between con man and killer, spectacle and truth — and why America has always been fascinated by men who build empires on deception.

Buckle up.

Because this isn’t just a murder story.

It’s a story about ambition without conscience.

Hosted on Acast. See acast.com/privacy for more information.

Welcome to Season 3 of Caviar & Criminals.

Before Prohibition kings, before the mobsters you already know, there was Stephanie St. Clair.

In our Season 3 premiere, Anthony takes Dana deep into the life of the Harlem numbers queen who refused to be erased, intimidated, or pushed aside. From her rise in New York’s underground economy to her very public war with corrupt police and powerful gangsters, Stephanie St. Clair was strategic, outspoken, and always several moves ahead.

Known for her sharp intelligence, fearless letters to the press, and absolute refusal to play small, Stephanie didn’t just survive a system built to crush her — she outsmarted it. And yes… along the way, she was very much bumping right along.

This is the story of power, defiance, and a woman who demanded respect in a world that never intended to give it to her.

Be pretty. Be petty. Be ready. 🎙️

Hosted on Acast. See acast.com/privacy for more information.

🎄 Holiday Surprise Drop! 🎄

This Christmas Day, we’re pulling something straight from the Caviar & Criminals vault — an episode we truly never thought would see the light of day.

Red, White, and Sleigh is our festive gift to you: a wildly unhinged, surprisingly informative, and very merry deep dive where Dana tells Anthony the story of American Girl dolls. Yes. Those dolls. The historical icons. The catalogs. The lore. The emotional damage.

What starts as a nostalgic trip through colonial kitchens and pioneer hardships quickly turns into a full-blown investigation of American Girl mythology, cultural impact, and why these dolls had an entire generation in a chokehold. Anthony comes in mostly unprepared. Dana comes in with facts. Chaos ensues.

This episode is silly, cozy, and a little unhinged — the perfect palate cleanser for the holidays and a reminder that sometimes the real crime is how deeply we all cared about fictional children in the 1700s.

Pour some eggnog, hide from your relatives, and enjoy this very special Christmas surprise drop from us to you.

🎁🎄 Happy Holidays from Caviar & Criminals.

Hosted on Acast. See acast.com/privacy for more information.