Five cigar smoking crime bosses – part 3
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 and part 2 here.
The five families
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 Genovese crime family also sometimes referred to as the Westside, is an Italian-American Mafia crime family and one of the “Five Families” that dominate organized crime activities in New York City and New Jersey as part of the American Mafia. They have generally maintained a varying degree of influence over many of the smaller mob families outside New York, including ties with the Philadelphia, Patriarca, and Buffalo crime families.
The current “family” was founded by Charles “Lucky” Luciano and was known as the Luciano crime family from 1931 to 1957, when it was renamed after boss Vito Genovese. Originally in control of the waterfront on the West Side of Manhattan as well as the docks and the Fulton Fish Market on the East River waterfront, the family was run for years by “The Oddfather”, Vincent “The Chin” Gigante, who feigned insanity by shuffling unshaven through New York’s Greenwich Village wearing a tattered bath robe and muttering to himself incoherently to avoid prosecution.
Charles ‘Lucky’ Luciano
Luciano stands out as the most influential mobster of the twentieth century. In the early 1930s, he orchestrated the eradication of the traditional Sicilian-style Mafia, subsequently joining forces with Meyer Lansky to establish the national syndicate. This syndicate unified diverse ethnic crime groups, placing the commission at the helm of various illicit enterprises, including bootlegging, prostitution, narcotics, gambling, loan sharking, and labour rackets. Luciano’s strategic vision and collaborative efforts reshaped the organized crime landscape, solidifying his position as a key figure in the underworld’s evolution during that era.

Vito Genovese
Much like Albert Anastasia of the Gambino family (see our previous article (Lewis, please add link)), Vito Genovese possessed a penchant for violence, but he also exhibited cunning intellect. Known as “Don Vito,” Genovese, a prominent narcotics kingpin, sought to assert dominance over the Luciano family in the 1950s, orchestrating the elimination of several high-ranking mobsters. However, his adversaries devised a plot to implicate him in a drug-smuggling scheme, leading to Genovese’s incarceration. Despite his strategic prowess, the intricate web of underworld politics eventually caught up with the formidable mobster.
Frank Costello
Renowned for his adept dealings with politicians, law enforcement, and judges, Costello earned the epithet “Prime Minister of the Underworld.” A significant figure within the national crime syndicate, he played a crucial role in securing protection for various criminal organizations. Costello’s resilience was evident when he survived an assassination attempt in 1957, a testament to his shrewd navigation of the criminal underworld. Eventually, he chose to retire from the Mob, marking the conclusion of a storied and influential chapter in his criminal career.
Costello liked cigars, but was a chain smoker of cigarettes. He smoked up to three packs of English Oval cigarettes a day. That caused his voice to change to the raspy voice he is now remembered by.

Antony ‘Fat Tony” Salerno
Salerno, a native of East Harlem, New York, was raised in an environment steeped in underworld activities. During his formative years, he immersed himself in various illicit endeavours, including gambling, running numbers, loansharking, and providing protection for the Luciano family, later recognized as the Genovese family. Affiliated with the 116th Street Crew under the leadership of Michael “Trigger Mike” Coppola, Salerno quickly became a key player in the criminal operations.
His ascent within the family ranks was marked by his control over a potentially lucrative numbers racket in Harlem, generating an estimated million dollars annually, along with a significant loansharking enterprise. Following Coppola’s departure to Florida in 1948 to evade murder charges, Salerno assumed command of the crew.
Notably, Domenick Lombardozzi portrayed Fat Tony in Martin Scorsese’s cinematic masterpiece, “The Irishman,” sharing the screen with iconic figures such as Robert De Niro, Joe Pesci, and Harvey Keitel. Lombardozzi’s portrayal, with a cigar in almost every scene, added a layer of authenticity to the film, capturing the essence of characters deeply embedded in the intricate web of organized crime.
Michael “Mikey Cigars” Coppola
Michael J. Coppola, widely known as “Mikey Cigars,” is a prominent American mobster and captain affiliated with the Genovese crime family, particularly active within their New Jersey faction. Born on May 18, 1946, Coppola garnered national attention when he eluded authorities for an impressive 11 years to evade a potential murder conviction. It’s crucial to distinguish him from Michael “Trigger Mike” Coppola (1900–1966), another member of the Genovese family.
Coppola’s association with the Genovese family traces back to the 1960s, marking the beginning of a long and impactful tenure. He attained the status of a made man in the late 1970s, gaining recognition as a member of “The Fist,” a Genovese hit team tasked with executing orders from the family administration during the late 1970s and 1980s, as documented by government sources.
Beyond his involvement in organized crime’s violent undertakings, Coppola played a significant role in labour racketeering within the trucking industry and New Jersey docks. His criminal activities led to a prison sentence of nearly five years, spanning from 1979 to 1983, for charges related to conspiracy and extortion.
During Tino Fiumara’s incarceration in the 1980s and 1990s, Coppola assumed the role of an acting caporegime (captain), overseeing the day-to-day operations of the New Jersey faction. Operating with precision, he received and relayed orders, showcasing his influence and leadership within the Genovese crime family’s intricate hierarchy.
Header photo by Rock Staar on Unsplash






