Special Guest: Bobby Duncan (The Cigar District)

In this episode of The Third Pour, Izzy and The Doc are joined by a true connoisseur of the leaf, Bobby Duncan from The Cigar District. We’re stepping into the lounge to explore the intricate relationship between premium tobacco and high-end bourbon whiskey.

The centerpiece of today’s pour is the Penelope Cigar Blend, a whiskey specifically crafted to stand up to the bold flavors of a fine smoke. To put it to the ultimate test, we’re pairing it with the legendary Davidoff Winston Churchill The Late Hour—a cigar known for its rich, cask-aged complexity.

In this episode, we discuss:

• The Cigar District Experience: Bobby shares his journey and what makes his shop a destination for enthusiasts.

• The Science of Pairing: Why certain mash bills complement specific wrappers and regions.

• Tasting Notes: A real-time breakdown of how the Penelope finish evolves when introduced to the dark, robust notes of the Davidoff.

• The Culture: Why the bond between bourbon and cigars remains one of the most storied traditions in the spirits world.

Whether you're a seasoned aficionado or just starting to build your first humidor, grab a cutter and a glencairn for this one.