Cigars have long been associated with power, luxury, and influence. In the world of organized crime, this association is amplified. The image of a mafia boss puffing on a cigar has become an iconic symbol, representing not just personal indulgence but also status and authority. This article delves into the preferred cigars of some infamous mafia bosses from the United States and Italy, exploring the history and cultural significance of cigars within organized crime.

The History of Cigars and Organized Crime

Prohibition Era: The Rise of the American Mafia

The relationship between cigars and organized crime dates back to the early 20th century, when Prohibition in the United States (1920-1933) led to the rise of powerful mafia families. These families controlled the illegal production and distribution of alcohol, amassing great wealth and influence. Cigars, often seen as a symbol of success and power, naturally became a part of the mafia culture. They were used to celebrate victories, seal deals, and establish a commanding presence.

During Prohibition, figures like Al Capone dominated the underground scene. The wealth generated from bootlegging allowed these crime lords to indulge in luxuries previously reserved for the upper echelons of society. Cigars, especially high-end ones from Cuba, became a status symbol. The act of smoking a cigar in public was a display of power and wealth, often used to intimidate rivals and impress allies.

Post-Prohibition and the Golden Age of the Mafia

After the repeal of Prohibition, the mafia diversified its operations into other illegal activities such as gambling, drug trafficking, and extortion. The wealth and influence of mafia families continued to grow, and so did their taste for luxury cigars. The mid-20th century is often considered the golden age of the American mafia, with figures like Charles “Lucky” Luciano and Vito Genovese shaping the structure and operations of organized crime.

During this period, the image of the cigar-smoking mob boss was cemented in popular culture. Hollywood films and media depictions played a significant role in romanticizing and dramatizing the lives of these criminals. The cigar became an essential prop in these portrayals, symbolizing the mix of sophistication and menace that characterized the mafia.

The Italian Connection: Cigars and the Cosa Nostra

In Italy, the connection between cigars and the mafia is equally significant. The mafia, or “Cosa Nostra,” has its roots in the late 19th century in Sicily. As the mafia grew in power and influence, so did their taste for luxury items, including fine cigars. Cigars became a symbol of their status and authority, much like in the United States.

The Sicilian mafia’s adoption of cigars mirrored the cultural values of respect, honor, and power that were central to their organization. High-ranking members would often use cigars to assert their dominance and command respect from their subordinates. The exchange of cigars in meetings was a ritualistic practice, symbolizing trust and mutual respect among members.

The Preferred Cigars of Infamous Mafia Bosses

Al Capone (1899-1947)

Al Capone, perhaps the most notorious gangster in American history, ruled Chicago with an iron fist during Prohibition. Known for his extravagant lifestyle, Capone had a particular fondness for Cuban cigars, specifically the H. Upmann brand. These cigars, known for their smooth and rich flavor, were a staple in Capone’s repertoire, symbolizing his wealth and power.

Capone’s choice of H. Upmann cigars reflected his desire to project an image of sophistication and control. The brand’s reputation for quality and luxury aligned with Capone’s persona as a powerful and influential figure. Smoking these cigars in public was a deliberate act, meant to reinforce his status and intimidate his rivals.

Charles “Lucky” Luciano (1897-1962)

Charles “Lucky” Luciano is credited with organizing the structure of the modern American mafia. He was instrumental in creating the National Crime Syndicate and establishing the “Commission” to mediate disputes between mafia families. Luciano’s cigar of choice was the Romeo y Julieta. These Cuban cigars, known for their balanced and aromatic blend, were a reflection of Luciano’s sophisticated and strategic mind.

Luciano’s preference for Romeo y Julieta cigars highlighted his taste for elegance and his strategic approach to leadership. The cigar’s complex flavor profile mirrored Luciano’s multifaceted personality, combining charm with ruthless efficiency. Smoking these cigars during meetings was a way for Luciano to assert his authority and command respect from his peers.

Vito Genovese (1897-1969)

Vito Genovese, a powerful figure in the New York mafia, was known for his ruthless tactics and ambitious nature. Genovese favored Partagas cigars, particularly the Partagas Serie D No. 4. These cigars are known for their full-bodied and robust flavor, mirroring Genovese’s strong and commanding presence in the mafia world.

Genovese’s choice of Partagas cigars reflected his aggressive and dominant personality. The bold flavor of these cigars complemented his reputation as a formidable and unyielding leader. Smoking these cigars was a statement of his power and his willingness to use force to achieve his goals.

Salvatore “Totò” Riina (1930-2017)

Salvatore Riina, also known as “The Beast,” was a Sicilian mafia boss notorious for his brutality. As the head of the Corleonesi faction, he orchestrated numerous assassinations and terrorized Sicily for decades. Riina’s preferred cigar was the Davidoff. These cigars, known for their exquisite craftsmanship and luxurious taste, were a stark contrast to Riina’s violent and ruthless nature, highlighting the duality of his character.

Riina’s preference for Davidoff cigars illustrated the complex nature of his personality. Despite his brutal methods, he had a taste for the finer things in life. The luxurious quality of Davidoff cigars contrasted sharply with his ruthless actions, adding a layer of sophistication to his otherwise fearsome image.

John Gotti (1940-2002)

John Gotti, the “Teflon Don,” was the head of the Gambino crime family in New York City. Gotti’s flamboyant personality and high-profile lifestyle made him a media sensation. He was often seen smoking Cohiba cigars, specifically the Cohiba Robusto. These cigars, known for their bold and complex flavor, suited Gotti’s larger-than-life persona and his desire to be seen as the ultimate mafia boss.

Gotti’s choice of Cohiba cigars was a reflection of his need for attention and his desire to be perceived as powerful and influential. The bold flavor of Cohiba Robustos complemented Gotti’s assertive and charismatic personality. Smoking these cigars in public was a way for Gotti to reinforce his image and command respect from those around him.

The Cultural Significance of Cigars in the Mafia

Cigars have always been more than just a luxury item in the world of organized crime. They serve as a symbol of power, control, and success. For mafia bosses, smoking a cigar was a way to project their authority and dominance. It was also a means of celebration, marking significant achievements and milestones.

In mafia meetings, the act of sharing a cigar could signify trust and camaraderie. It was a ritual that helped to build and strengthen relationships within the organization. The choice of cigar could also reveal a lot about a boss’s personality and taste, adding another layer to their carefully crafted image.

Parallels to Modern Day: What Your Cigar Says About You

In contemporary society, cigars continue to be a symbol of status and sophistication. The type of cigar one chooses can reveal indicators of personality and taste to others around them, much like it did for mafia bosses. Here are a few parallels:

• Luxury Brands (e.g., Cohiba, Davidoff): Choosing a high-end cigar can indicate a taste for luxury and a desire to be seen as sophisticated and influential. It reflects a sense of accomplishment and a preference for the finer things in life.
• Classic Brands (e.g., Romeo y Julieta, Montecristo): Opting for a classic brand suggests a respect for tradition and a refined palate. It can also signify a strategic and thoughtful approach to decision-making, much like Luciano’s preference for Romeo y Julieta.
• Bold and Robust Cigars (e.g., Partagas): Selecting a cigar with a strong flavor profile can indicate a bold and assertive personality. It suggests confidence and a willingness to take risks, akin to Vito Genovese’s choice of Partagas cigars.
• Smooth and Mellow Cigars (e.g., H. Upmann): Favoring a smoother, more balanced cigar can reflect a calm and controlled demeanor. It indicates a preference for quality and a sophisticated taste, similar to Al Capone’s fondness for H. Upmann cigars.

Wrap Up

The relationship between cigars and mafia bosses is a fascinating blend of culture, power, and symbolism. From the streets of Chicago to the hills of Sicily, cigars have played a significant role in the world of organized crime. They are not just a luxury, but a statement of authority and influence. The preferred cigars of infamous mafia bosses, such as Al Capone’s H. Upmanns and John Gotti’s Cohibas, reflect their personalities and their place in the criminal underworld.

For modern cigar enthusiasts, the choice of cigar can similarly reveal much about one’s personality and taste. Whether opting for a luxury brand, a classic favorite, or a bold and robust option, the cigar you choose is a reflection of who you are and how you wish to be perceived. Just as it did for the mafia bosses of yesteryear, the right cigar can make a powerful statement.