EPISODE 7

What Makes a Cigar Gentlemanly? A Deeper Look with Davidoff’s Alex Weghorn (Part II)

In this second half of Brian’s in-depth conversation with Alex Weghorn of Davidoff Cigars, we journey further into the thoughtful world of cigar craftsmanship and the deeper meaning behind a gentleman’s rituals.

Alex demystifies the aging process of cigars, explains how environmental factors shape tobacco character, and draws compelling parallels between wine, tailoring, and cigar rolling. But this episode isn’t just about cigars—it’s about intention, gratitude, and how the art of slowing down reveals what matters most.

Together, Brian and Alex explore how refinement isn’t defined by price, but by appreciation. Whether it’s food, clothing, or tobacco—the true gentleman knows how to elevate a moment by being fully present in it.

0:00 Intro

1:05 How tobacco aging works

4:58 Post-fermentation grades and blending variables

6:55 Why upper leaves carry more flavor

9:33 Tobacco vs. wine: how climate and care shape both

14:46 Crop to shop: Davidoff’s selective retail model

20:31 Make the cigar the occasion

22:54 What makes a cigar “gentlemanly”?

25:22 How the gentlemanly lifestyle shows up in Alex’s life

27:43 Why flavor pairing is a creative, cultural pursuit

30:07 Preparedness, opportunity, and the real meaning of “luck”

33:00 The role of gratitude in a gentleman’s life

37:44 Final thoughts and preview of a possible round three