Five cigar smoking crime bosses (part 2)
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.
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. You can read part one of the series by clicking this link
In this list, we look at one of the five families. The Five Families refer to five Italian American Mafia crime families that operate in New York City. In 1931, the five families were organized by Salvatore Maranzano following his victory in the Castellammarese War.
Maranzano reorganized the Italian American gangs in New York City into the Maranzano, Profaci, Mangano, Luciano, and Gagliano families, which are now known as the Bonanno, Colombo, Gambino, Genovese, and Lucchese families. Each family had a demarcated territory and an organizationally structured hierarchy and reported to the same overarching governing entity. Initially, Maranzano intended each family’s boss to report to him as the capo dei capi (“boss of all the bosses”).
The Gambino Family was very influential and was brought down, together with the other families, by a team led by United States Associate Attorney General Rudy Guiliani, who will also appear on our list of five cigar smoking politicians, which we will publish in a later stage. Ironically, at the time of writing of this article, Guiliani is in legal problems because of his connection to Donald Trump and the false accusations about voter fraud. Guiliani might end up behind the same bars where he locked up members of the five families. In 2023, a relative of the Gambino family, Giovanni Gambino, started Gambino Cigars.
Carlo Gambino
Of course the list has to start with the patriarch of the family, Carlo Gambino. The crime outfit was named after him so he deserves to be number one on our list.
Carlo Gambino, the inspiration for Mario Puzo’s iconic “Godfather” character, was renowned for his strategic acumen and preference for maintaining a discreet profile within the Mafia. Notably, Gambino distinguished himself as one of the rare Mafia bosses to evade imprisonment, contributing to his reputation as a shrewd and elusive figure.
However, beyond his criminal enterprises, Carlo Gambino had a notable passion for cigars, adding a distinctive layer to his persona. In addition to his adept leadership skills within the Gambino crime family, Gambino was known to appreciate the finer things in life, and cigars were among his indulgences.
While navigating the intricate world of organized crime, Gambino found solace and pleasure in the ritual of enjoying a well-crafted cigar. The love for cigars became a part of his identity, offering a glimpse into the more personal aspects of his character. This passion for cigars, coupled with his astute leadership, further solidified Carlo Gambino’s complex legacy.
In the annals of Mafia history, Carlo Gambino’s story stands out not only for his criminal prowess but also for the nuanced details that reveal the man behind the crime boss image. The intertwining of his strategic mind with the appreciation for the simple pleasures of life, such as a finely rolled cigar, paints a more comprehensive picture of this enigmatic figure in American organized crime.
Albert Anastasia
An individual known for his extreme propensity for violence, Anastasia held the position of chief executioner within Murder Inc., the enforcement arm of the 1930s national crime syndicate that carried out over 400 murders. His quest to encroach upon Meyer Lansky’s Havana casino operations ultimately led to his demise when he was ruthlessly gunned down in a Manhattan barbershop in 1957.
John Gotti
The late Gotti, renowned as the Dapper Don for his sartorial elegance and the Teflon Don for his remarkable ability to sidestep convictions, ascended to power after the assassination of Paul Castellano. Recognized as a ruthless leader, Gotti’s criminal reign came to an end in 1992 when he was convicted on charges of murder and racketeering, resulting in a life sentence behind bars.
In a notable interview with Cigar Aficionado, Gotti disclosed that his preferred cigar was the Gurkha Grand Reserve Churchill. The choice of the Gurkha Grand Reserve Churchill as his favorite cigar offered a glimpse into Gotti’s personal tastes, blending a penchant for luxury with the gritty reality of his involvement in organized crime.
Picture from cigarspiritsmagazine, photo by Matt Furman
Paul Castellano
Appointed as the boss by his brother-in-law Carlo Gambino, Big Paul Castellano broadened the family’s reach into the garment, trucking, and construction rackets. However, despite his expansion efforts, Castellano failed to earn the respect of his subordinates. When he began discussing Mafia affairs indiscreetly, he met a tragic end, being gunned down in front of Sparks Steak House in Manhattan in 1985. Notably, Castellano had a fondness for cigars.
Joseph Francolino
Joseph “Joey Cigars” Francolino, a soldier in the Gambino family, assumed control of the family’s waste management operations following Jimmy Failla’s imprisonment in the 1990s. Known for his flamboyant style, Joey was recognized for his penchant for hand-tailored suits, extravagant jewellery, a luxurious residence in Staten Island, yachts, and high-end cars. His ostentatious lifestyle reflected his success in the organized crime world. Sadly, Joey Cigars passed away in 2021 at the age of 83.
Header photo by Rock Staar on Unsplash
