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…

Few American presidents are as closely associated with cigars as John F. Kennedy. Known for his charm, sophistication, and cool demeanor, JFK was an avid cigar smoker, with a particular preference for Cuban cigars. Yet, ironically, it was Kennedy who signed the Cuban trade embargo in 1962, cutting off America’s access to the very cigars he enjoyed.

Let’s explore the facts, myths, and lasting impact of JFK’s relationship with cigars.

For centuries, tobacco shaped American trade, culture, and politics—from Virginia’s plantations to early political halls. Yet, in the 18th century, while the Founding Fathers cultivated and traded tobacco, cigars were not yet widely smoked.

Instead, early Americans preferred pipes, snuff, and chewing tobacco, and it wasn’t until the early 19th century that cigars gained real popularity. The War of 1812 played a pivotal role in this shift—marking the true beginning of America’s long history with cigars.

The Battle of Antietam, fought on September 17, 1862, was one of the most consequential engagements of the American Civil War. It marked the bloodiest single day in American military history, with over 22,000 casualties. Amid this pivotal moment, a misplaced envelope containing three cigars and Confederate General Robert E. Lee’s Special Order 191 altered the war’s trajectory in a way that continues to intrigue historians.