5 Cigar Smoking Crime Bosses – Part 1

Back in the early days of cinema, heroes often smoked cigars. Think about Clint Eastwood and John Wayne in their western movies. But it slowly changed to gangsters smoking cigars, especially mafia bosses in all the Martin Scorsese directed movies and later in series such as The Sopranos. Cigar Inspector is working on a list of ‘cigars in cinema’, keep an eye out for that extensive list.

But in some cases, the crime bosses were based on real characters, on real mafia members that smoked cigars in real life. In this article, we will name five. But we can tell you, the list is bigger, so big that we split it into several ‘top 5’ lists. If you know any cigar loving criminals, create a free account and let us know in the comments. We would love to hear your input.

If you wonder where Inspector X got the inspiration for this series, read our article about the cigar lounges of Bangkok. Two of the lounges Inspector X recently visited in Bangkok are 1920’s themed, with Abandoned Mansion taking the 1920’s crime scene to the next level with cocktails named after famous gangsters.

Al Capone

One of America’s most infamous criminals, Al Capone underwent a transformative journey from a ruthless thug to a shrewd “businessman.” His tight grip on bootlegging, gambling, and prostitution solidified his status as a prominent public figure. Emerging victorious in the tumultuous gang wars of the 1920s, this flamboyant mobster asserted complete dominance over Chicago. However, his reign came to an abrupt end when he was ultimately brought down by charges of tax evasion. To truly understand the complexity of Capone’s rise and fall, delving into the historical context of his era provides a deeper insight into the intricate tapestry of his criminal empire. Capone was a passionate cigar smoker; his most famous picture shows him with a cigar as well. That there are machine-made, flavoured cigarillos for sale bearing his name now would be an insult to this lover of the fine leaf.

Dutch Schultz

A mercurial yet enterprising figure in the underworld, Dutch Schultz left an indelible mark on the criminal landscape. During the 1920s, he seized control of the Bronx beer trade and dominated the penny-ante numbers game in Harlem. Evading conviction for income tax evasion added to his mystique, but the tide turned when he openly threatened to kill special prosecutor Thomas E. Dewey, who was actively investigating vice and racketeering. This audacious move marked Schultz’s downfall, leading to the necessity of his removal from the criminal equation. Examining the historical backdrop of Schultz’s era unveils the intricate dynamics that fuelled his rise and precipitated his dramatic demise. Dutch was often seen with a cigar in his mouth.

Sam “Momo” Giancana

Sam Giancana, an unrelenting mob boss with a dark legacy marked by numerous fatalities, faced the law with over 70 arrests during his criminal career. His ascent to power within the Chicago Outfit was solidified through strategic orchestration, particularly in the takeover of the numbers racket. However, Giancana’s erratic involvement in peculiar ventures, such as purportedly supporting CIA initiatives to eliminate Fidel Castro and allegedly orchestrating the death of Desi Arnaz, eventually led to his ousting from power and, ultimately, his demise. Delving into the historical details of Giancana’s life provides a more nuanced understanding of the complex web of criminal enterprises and high-stakes intrigues that defined his tumultuous reign. Giancana smoked so many cigars that his nickname was Sam the Cigar.

Bugsy Siegel

In his adolescence, Bugsy Siegel co-founded the Bug and Meyer Mob alongside Meyer Lansky, specializing in managing contracts for bootleg gangs and often personally executing the associated murders. Transitioning to the 1930s, Siegel assumed control over the syndicate’s West Coast rackets, establishing connections with Hollywood luminaries while indulging in a notable cigar hobby. His trajectory reached a dramatic climax in 1947 when he met his demise, accused of embezzling funds from the Flamingo in Las Vegas. Examining Siegel’s multifaceted life, including his ventures in organized crime and his penchant for cigars, adds a layer of richness to the historical tapestry of this enigmatic figure.

Meyer Lansky

Meyer Lansky, the mastermind behind the national crime syndicate, played a pivotal role in its financial operations, entrusted with concealing and investing vast sums of money. Revered as the brains of the organization, Lansky’s influence was paramount, and major decisions were rarely finalized without consulting the “Little Man.” Lansky’s imprint extended to a virtual gambling monopoly in pre-Castro Cuba, where his strategic prowess contributed to substantial wealth accumulation. Additionally, his inclination for skimming millions from Las Vegas casinos further solidified his financial success. Beyond his criminal enterprises, Lansky was also known for his love of cigars, adding a distinctive touch to the multifaceted persona of this influential figure in organized crime history.

Header photo by Rock Staar on Unsplash