Native to the Americas, the tobacco plant has been used by indigenous Mesoamericans and South Americans for millennia, long before the practice of chewing, smoking, and snuffing its leaves became a global phenomenon. “When Columbus stumbled upon the Americas in 1492, he also discovered tobacco; the New World's natives smoked cylindrical bundles of twisted tobacco leaves wrapped in dried palm or corn husks.”
Referred to as sicars, or sikars, by the Mayans, these once-large bundles soon evolved into their much smaller contemporaries, the cigars. Because quality hand-rolled cigars were and continue to be primarily sourced from in and around Central America, they can be quite expensive. As a result, cigars naturally became a symbol of status, power, and authority by the 19th century – a notion reinforced by their idiosyncratic appearances in popular culture, often in relation to all-around “bad guys” of the criminal underworld.
But where, does this stereotype come from? “Cigars have traditionally been viewed as expensive, imported, hand-crafted items that corporate and political leaders consume,” writes digital media executive Jeremy Frommer. “Smoking an exclusive brand of cigar is symbolic of membership, social position and level of corporate success.” For example, throughout history, a number of prominent casino owners and their high-roller patrons were cigar aficionados with ties to the criminal world.
Furthermore, the association between crime and cigar culture has been a long-standing one in Hollywood, and the film industry in general. Though smoking was once a perfectly acceptable habit for the heroes of cinema, with ever-greater knowledge of its detrimental effects and the general dangerous nature of the industry in general, the cigarette smoking good guy, like Humphrey Bogart (1899 – 1957) for example, has by and large disappeared.
But for a lack of smoking protagonists, villains have gone on to “take up the slack,” argues Aljean Harmetz. “Like most of today's villains, Robert De Niro's tattooed sociopath in Cape Fear  wouldn't have been complete without a smoke, that necessary proof of evil—and of sadism,” he writes. “So if heroes can't smoke, villains are almost obligated to strike a match and reach for a butt.”
We see this characteristic trope repeated throughout various forms of fiction. A few good examples include The Sopranos’ (1999 – 2007) titular anti-hero Tony Soprano played by the late James Gandolfini (1961 – 2013), or the famous bootlegger Forrest Bondurant played by Tom Hardy in the fictionalized 2012 film Lawless. Comic books also have their share of cigar-chomping villains. Consider Ethan Roark, Sin City’s (1991 – 2000) corrupt and stogie-smoking senator, or the rotund and white-clad Marvel super villain Kingpin.
But, as previously mentioned, the relationship between crime and cigars smokers has a firm basis in reality. Numerous gangsters in the Italian-American and Sicilian Cosa Nostra are or were well-known cigar aficionados. Mobsters like Michael “Mikey Cigars” Coppola, Robert “Bobby the Cigar” DeLuca, Salvatore “Sam the Cigar” Giancana (1908 – 1975), and Carmine “Cigar” Galante (1910 – 1979) are or were presumably nicknamed for enjoying cigars.
The trope of the cigar-smoking gangster has snuck its way into capitalism. Bicycle Playing Cards, one of the world’s most iconic brands of playing cards, may soon introduce a line of 1920s mafia-themed cards called “MADE.” Different editions of the deck will feature intimidating mobsters smoking cigars, looking generally suave yet seedy, in place of various kings, queens, and the like. Similarly, the Polish board game “Mafia” (2007) features a cigar-sucking mobster on its box set’s front. So too does “Mafia: Vendetta” (2012).
Expectedly, tobacco companies – and/or their subordinate cigar brands – are also cashing in on the allure of the mostly bygone days of the cigar smoke haze. A popular line of cigarillos (small cigars) simply called Al Capone is naturally named after the infamous Chicago crime lord. Similarly, a less popular brand of larger full-sized smokes, the Miami Mafia cigars blended with Dominican and Nicaraguan tobaccos, unashamedly takes its brand name from the mob.
And, in 2005, one of the most recognizable cigar brands called CAO, released its “Sopranos” line of cigars named after the HBO series and its main character, Tony Soprano, which makes sense since Soprano himself smoked a number of CAO cigars in the series. Interestingly, differently sized cigars, or vitolas, within the line are named after various roles within the mafia hierarchy, as well: “Associate,” “Boss,” and “Soldier” make up three sizes in the “Sopranos” line.
Cigar smoking is also part of mythology. Back in the historical neighborhood of Tampa’s historic Ybor City neighborhood - a former cigar manufacturing powerhouse as well as occasional criminal hideout – seems to have a resident ghost. El Fumador, or “The Smoker,” is the wandering spirit of a former president of the famous Cuban Club, also called El Circulo Cubano de Tampa. It was century-old community center erected as a gathering place for the many Cuban migrants who used roll cigars en masse at his factories.
Though smoking rates in many parts of the developed world have gone down considerably over time, and cigar smoking now seems to be something of a rarity, the popular image of the cigar-smoking gangster and the stogie-chewing mobster, refuses to die. The image of the Don or plain old “made man” lighting one up will probably stick around as a popular conception for a long time, as does the Cuban Club’s Smoker, resolutely refusing to leave this world.