Cigars have always had a quiet presence in American life. From colonial fields to corner offices, they’ve passed through the hands of farmers, presidents, entertainers, and everyday workers. This post offers a wide-angle view of the cigar’s journey through American history. We’ll trace its path from colonial farms and frontier saloons to presidential portraits and today’s curated rituals. Along the way, we’ll explore how cigars have influenced and been influenced by shifting ideas of work, leisure, class, and culture. Whether you’re a longtime enthusiast or simply curious about the historical appeal, this is a story worth exploring, one puff at a time.
Indigenous Roots
Long before the birth of the United States, tobacco held deep meaning for Native American tribes across the continent. For the Iroquois, Lakota, Cherokee, and many others, it was far more than a plant, it was a sacred medium for ceremony, healing, and connection. Smoked in peace pipes to mark agreements, offered in prayer, and used in rituals of renewal, tobacco was woven into the spiritual and social fabric of tribal life.
When European settlers arrived in the 17th century, they encountered this reverence with fascination. Tobacco, unfamiliar yet compelling, quickly captured their attention, not just for its aroma and effects, but for its role in Native customs. What began as cultural exchange soon evolved into cultivation, as settlers recognized tobacco’s potential as a valuable crop. Within a few decades, it became one of colonial America’s first economic engines, linking indigenous tradition with emerging global trade. This early chapter marks the beginning of tobacco’s complex journey through American history.
Early American History
In the early 1600s, settlers in Virginia began cultivating tobacco for export. John Rolfe, best known for having married Pocahontas in 1614 and for being the first to cultivate marketable tobacco in Virginia, successfully hybridized Caribbean Nicotiana tabacum with native strains producing a sweeter, milder leaf that quickly captivated English markets. By 1619, tobacco had become so valuable it was used as currency in the colonies, a commodity that could pay taxes, buy land, and settle debts.
In the Connecticut River Valley tobacco farming took root as early as the 1630s. Settlers in Windsor, Connecticut, allied with local tribes and began growing Nicotiana rustica, a potent native variety later replaced by milder strains imported from Virginia and Barbados. By the mid-1600s, the Connecticut General Court enacted protectionist laws requiring residents to smoke only locally grown tobacco unless licensed otherwise, marking a striking early example of regional pride and economic self-defense.
By the 1700s, the colonies were exporting tens of millions of pounds annually. While cigarettes and cigars were still rare, pipe smoking and snuff were common among elites, and tobacco was deeply woven into the social fabric of early America. By the early 1800s, Connecticut tobacco was being exported to England and the region had become a major supplier of cigar wrapper leaf. Broadleaf tobacco, stalk-cut and sun-cured, was prized for its durability and flavor. Family farms and small workshops began hand-rolling cigars, laying the groundwork for a cottage industry that would later industrialize.
By the mid-19th century, cigars had become a fixture in the lives of urban professionals, politicians, and cultural elites. To meet growing demand, cigar factories flourished in New York, Pennsylvania, and Florida, employing thousands of skilled immigrants, many of them Cuban, Spanish, and German, who brought craftsmanship and tradition to the industry. At the same time, Connecticut’s tobacco farms evolved into a key supplier of premium wrapper leaves, with the introduction of shade-grown techniques. These innovations produced thinner, silkier wrappers prized for their elegance, helping define the aesthetic and quality standards of American cigars.
A Brief Chapter in the Civil War Era
By the time the Civil War erupted, cigars had become a fixture of American leisure and leadership. In both the North and South, tobacco was not only an economic pillar, but a cultural emblem. Generals like Ulysses S. Grant famously smoked cigars throughout the war, with Grant receiving thousands by mail after his habit was publicized, turning the cigar into a symbol of Union resolve and personal grit.
One of the war’s most dramatic episodes involved cigars directly: in September 1862, Union soldiers discovered three cigars wrapped around Confederate General Robert E. Lee’s lost marching orders, Special Orders No. 191, in Frederick, Maryland. This intelligence gave Union General George McClellan a rare strategic advantage at the Battle of Antietam, leading to the bloodiest single-day battle in American history and paving the way for Lincoln’s Emancipation Proclamation. Certainly making these cigars the three most important in American History.
For everyday soldiers, tobacco, especially cigars and plug tobacco was a constant companion. It was included in rations, traded between camps, and shared in moments of rest. Smoking offered comfort, camaraderie, and a brief escape from the brutality of war. Whether rolled by hand or gifted from home, cigars became part of the soldier’s identity, being smoked in the trenches, and passed around campfires.
Late 1990’s Industrialization and Expansion
The late 19th century saw a boom in cigar production. Mechanization allowed for mass manufacturing, and cities like Tampa, Key West, and New York became cigar hubs. Tampa’s Ybor City, founded by Cuban immigrant Vicente Martinez-Ybor, became known as the “Cigar Capital of the World.” Immigrant labor fueled production while Connecticut’s shade-grown tobacco gained prestige among premium manufacturers. Cigar rollers were respected for their skill, and cigar factories became hubs of both craftsmanship and community.
At the turn of the century, cigars had become part of the American rhythm. No longer reserved for the wealthy, they were now within reach of the working class, filling with tobacco scent the barbershops, saloons, and office lounges of the time. Presidents like Theodore Roosevelt and William Howard Taft were frequently photographed with cigars in hand, reinforcing the image of pride, masculinity, and aspiration between aficionados.
The Roaring and Smokiest 20’s
Was a decade of defiance and indulgence. With Prohibition in full swing, Americans went underground. Speakeasies came alive with jazz, bootleg whiskey, and the unmistakable scent of cigars, each puff a quiet rebellion against the big man. Cigars became symbols of freedom and flair, embraced by everyone from jazz musicians to mob bosses. Figures like Al Capone, who famously favored Hav-A-Tampa cigars, turned cigar smoking into part of their larger-than-life persona, while George Burns, with his ever-present El Producto Queen cigar, brought a touch of humor and charm to the trade and legendary musician Louis Armstrong even had a cigar named after him.
Cigar smoking captured the spirit of the age, bold, stylish, and unapologetically alive, tapping into the American desire for escape and expression. An indulgence that celebrated the free American spirit with every smoky exhale.
The Great Depression: Grit and the Working Man’s Smoke
During the Great Depression cigars remained a quiet companion to resilience. Though luxury consumption declined, tobacco endured as an affordable comfort. Factory workers, laborers, and street vendors often turned to cigarillos and plug tobacco, being cheaper alternatives that still offered a moment of escape. In breadlines and union halls, cigars were passed between hands as a symbols of solidarity and cigar brands adapted by offering budget lines that kept the tradition alive.
Golden Age of Hollywood: Prestige, Persona, and Pop Culture
From the late 1930s to the 1950s, cigars burned brightly in the spotlight of Hollywood’s golden age. They weren’t just props, they were emblems of charisma, control, and cinematic allure. Leading men like Clark Gable and Edward G. Robinson made cigars part of their signature style, blending rugged masculinity with refined confidence. Behind the camera, studio moguls such as Darryl F. Zanuck and Louis B. Mayer wielded cigars like scepters of influence. Their smoke-filled offices became the nerve centers of American entertainment where deals were struck, and stars were made.
This allure soon moved beyond the silver screen, settling into boardrooms and corner offices across America. Cigars became synonymous with success, mirroring the confident swagger of Madison Avenue executives and post-war businessmen. Like tailored suits and highball glasses, a cigar wasn’t just an indulgence, but a declaration of ambition and authority.
The 1950s And the Cigarette Boom
By the 1950s, the tobacco landscape began to shift. Filtered cigarettes, aggressively marketed as “safer” and modern, surged in popularity, especially among younger consumers and women. Their sleek packaging and convenience fit the fast-paced optimism of post-war America. Meanwhile, cigars began to lose ground. Though still respected in executive circles, they were increasingly seen as old-fashioned, and the cigar industry faced pressure to adapt. Some brands diversified into smaller formats, while others leaned into heritage and craftsmanship to preserve their identity amid the cigarette boom.
1960s Stability Amid Cultural Revolution
In a decade marked by protest, upheaval, and generational divides, cigars held firm as symbols of tradition and quiet authority. They remained the smoke of boardrooms, political backchannels, and institutional power, gracing the hands of figures like John F. Kennedy, who famously secured a cache of Cuban cigars before signing the Cuban embargo, and J. Edgar Hoover, whose image was steeped in control and continuity.
Brands like King Edward, White Owl, and Dutch Masters, all rooted in American production remained household staples, offering accessibility and familiarity. Meanwhile, premium names like Partagás, Punch, and H. Upmann gained cult status as Cuban imports became contraband under the embargo, transforming them into coveted symbols of exclusivity and nostalgia. Though the cultural spotlight shifted, cigars quietly preserved their role as markers of respectability and craftsmanship.
1970s Craft Over Consumption
In this decade the cigar enthusiast emerged as a quiet countercultural figure resisting the era’s growing consumerism and relentless pace. Cigar lounges and specialty shops offered refined alternatives like Macanudo, Punch, and Dominican-made Partagas, while early non-Cuban brands such as Joya de Nicaragua and Camacho introduced bold, earthy profiles. Smoking a cigar became a deliberate act of reflection and control, less about luxury and more about savoring time, honoring craftsmanship, and expressing personal style.
1980s Bold Flame
In the high-octane culture of the 1980s and early ’90s, cigars became emblems of power, wealth, and unapologetic success. Hollywood amplified this image, Scarface’s Tony Montana, Wall Street’s Gordon Gekko, and The Untouchables’ Al Capone all wielded the leaf. Off-screen, icons like Arnold Schwarzenegger and Jack Nicholson turned cigar smoking into a signature trait, reinforcing its association with masculine charisma. A few iconic women carved out space in the smoke-filled spotlight. Raquel Welch and Demi Moore appeared in interviews and photo shoots with premium smokes in hand, breaking stereotypes, opening new markets and inspiring a generation of female smokers who embraced the ritual with elegance and authority.
Executive lounges, country clubs, and magazine covers embraced cigar culture in a more cohesive way than previously done, cementing the cigar like a true iconic consumer product in the American culture. This resurgence fueled demand for both legacy and emerging brands. Romeo y Julieta, Padron, Oliva and La Flor Dominicana gained traction among aficionados and captivated a new generation of smokers.
1990s: The Cigar Renaissance
The 1990s marked a full-blown cigar renaissance in the United States. Cigars surged back into mainstream culture, not just as symbols of power, but as lifestyle statements. Fueled by economic optimism and a wave of nostalgia, cigar smoking became fashionable again among professionals, celebrities, and even younger audiences. Cigar Aficionado magazine, launched in 1992, played a pivotal role in glamorizing the ritual, pairing cigars with luxury, travel, and fine dining. Cigar lounges opened in major cities, and smoking became a curated experience.
2000s: Refinement, Regulation, and Cultural Persistence
The first decade of the 21st century brought a more nuanced chapter for cigars. While public smoking bans and health awareness challenged consumption, cigars retained their cultural appeal. They became less about mass consumption and more about personal enjoyment and moments of celebrations. Boutique brands gained traction among connoisseurs, while legacy names like Fuente and Padron continued to dominate. American cities like Miami and New York upheld cigar culture through exclusive lounges and events, even as Tampa Bay’s historic role faded further into memory. Foreign cigars from Nicaragua, Honduras, and the Dominican Republic became staples of American humidors, reflecting a global palate. In a fast-paced digital age, cigars offered something timeless: a pause, a conversation, and a connection to craft.
2010s and the Digital Era
The 2010s marked a pivotal shift in how cigars were enjoyed, shared, and celebrated across America. The rise of online retailers transformed access, empowering aficionados to explore blends, read reviews, and curate personal humidors from the comfort of home. At the same time, social media gave voice to a new generation of cigar influencers, reviewers, and lifestyle curators who fused tradition with contemporary flair.
In this decade, cigars evolved from symbols of status to expressions of connection. Whether paired with bourbon, coffee, or jazz, they became part of a broader movement toward intentional, high-quality consumption. Boutique brands flourished, attracting loyal followings with distinctive blends and stories while legacy houses like Arturo Fuente, Padrón, and Ashton remained cultural cornerstones.
2020s: Community, Craft, and the New American Ritual
The 2020s have ushered in a more expansive, inclusive, and digitally connected cigar culture, one that bridges the modern world with the vintage soul of the craft. Online purchasing has become standard, with sampler packs, curated subscription boxes, and brand storytelling through content creation redefining how cigars are marketed and experienced. Digital platforms now connect smokers across the country who share a deep appreciation for the leaf.
Cigar lounges have evolved into cultural hubs, welcoming veterans, entrepreneurs, artists, and newcomers alike. These spaces are no longer just for smoking; they’ve become places to network, exchange ideas, and build community. The American palate increasingly favors Nicaraguan blends, which now rival and often surpass Cuban cigars in quality. Dominican cigars lead in export volume, while Cuban cigars remain a romanticized ideal. Meanwhile, American-grown Connecticut wrappers and boutique blends from Florida and Pennsylvania are fueling a renewed appreciation for domestic tradition.
Today, cigars have become woven into the cultural heritage of the United States. For aficionados, they offer a moment of clarity, a shared passion, and a quiet rebellion against the rush of modern life. More than ever, cigars continue to illuminate the chapters of American culture one draw at a time.
About the Author
Rafa is a graphic designer and photographer with a keen eye for bold visuals and authentic storytelling. Born with a love for Nicaraguan tobacco, he infuses his creative work with the same rich, vibrant spirit of his heritage. When not crafting stunning designs or capturing life’s moments, Rafa’s enjoying the perfect cigar. Follow his artistic journey on Instagram @studio_rafael.
