In 1830s Havana, a Dutch-born cigarmaker named Gustave Bock solved a problem every modern brand still faces: how do you prove, at a glance, that what you're holding is the real thing? His answer became the oldest piece of brand identity in the modern cigar industry — and collectors have never stopped reading it.

JFK pairing his cigar with a cocktail.

The Bourbon & Cigar Pairing Wheel: bourbon flavor families on the left, cigar flavor families on the right.

When discussing the history of cigars in America, much of the focus is often placed on Cuban influences or European craftsmanship. However, African Americans played a significant yet often overlooked role in shaping the U.S. cigar industry—through labor, culture, and activism.

1.     JFK and the Cuban Cigar Embargo (1962)

4.     Bill Clinton and the Monica Lewinsky Scandal (1990s)

10. The Mafia and Cigar Lounges (1920s-1960s)

After John F. Kennedy and the Cuban Embargo (1962), there have been a few key figures and moments that significantly shaped cigar culture and the cigar market in the United States. While no single individual had quite the same impact as JFK, certain figures and events played pivotal roles in the evolution of cigar smoking post-embargo.

Three watershed moments…