Philip Lombardo (pronounced "loam-BAR-doh") (October 6, 1908 in New York City – April 1987) also known as "Benny Squint" and "Cockeyed Phil", was the boss of the Genovese crime family from the late 1960s until the beginning of the 1980s. Lombardo began his career as a soldier on Michael "Trigger Mike" Coppola's powerful 116th Street Crew in the East Harlem section of New York. During the 1940s, Lombardo served a brief prison stretch for narcotics trafficking, his only imprisonment. Due to his thick eyeglasses Lombardo earned the nickname, "Benny Squint."wikipedia

ROME - After 13 years on the run, the woman with 'the eyes of ice' who reputedly directed a crime syndicate for her imprisoned brother gave herself up to police who came knocking at dawn yesterday at a fortified villa outside Naples, police said.
The arrest of Rosetta Cutolo, 57, in the mob stronghold of Ottaviano was the second important strike by authorities at organised crime in less than a month.
Authorities believe Rosetta Cutolo had been running the syndicate for her brother, Raffaele Cutolo, who is serving a life sentence in a Sardinian prison for crimes in the name of his Nuova Camorra Organizzata, a powerful branch of the Camorra, as Neapolitan crime gangs are known.
Rosetta Cutolo is nicknamed 'ice eyes' for the hardened look from her blue eyes. She never married, apparently to devote her life to her brother. She had been sought since 9 September, 1981, when she was believed to have escaped during a police raid on a house in search of crime bosses. Independent news.

Pietro Aglieri (born June 6, 1959 in Palermo) is a Sicilian mafioso from the Guadagna neighbourhood in Palermo. He is known as U Signurinu ("The Little Gentleman") for his relatively sophisticated education and refined manners. He had a classical education and studied Greek, Latin, philosophy, history and literature to a level that guaranteed him entry to university. Instead he chose for a career in Cosa Nostra.In spite of his youth and misleadingnickname (the Little Gentleman), Aglieri was everybit as violent as the rest of the Corleone bosses
before him. wikipedia.

BARNES, Leroy (a.k.a. Mr. Untouchable; the King of Harlem)
Leroy “Mr. Untouchable” Barnes was a legendary drug dealer and crime boss in Harlem who was the John Gotti of his day,according to famed crime writer Jerry Capeci. Barnes was a well-known drug
dealer, and yet he survived numerous trials. The name “Mr. Untouchable” was given to him by the New York Times who featured him on the cover of their Sunday magazine. All the while he was dealing drugs, Barnes was also a deacon of a popular Harlem
church that was famed for giving out turkeys to needy families on Thanksgiving and toys to less-fortunate children on Christmas. Carlo Devito

CARLISI, Samuel (a.k.a. Sam Wings)
Sammy was the driver of Joey Aiuppa, former
Chicago Outfit boss. Sammy received his nickname
in the 1970s because he flew around the country as a
mob courier. He often represented Joseph Ferriola,
another high-ranking outfit capo, who suffered from
cancer.
Sammy was well known for racketeering, loan
sharking, and arson as well as several illegal gambling
businesses in the Chicago area and the west suburbs.
He was sentenced to prison where he died in 1997
Carlo Devito

Frank “The Prime Minister” Costello:
Also known as the “Chairman of the Board.” He was such a powerful mob boss that when he testified in front of the televised Kefauver Hearings looking into organized crime in 1951, he refused to let the cameras show his face. They showed only his hands and viewers heard only his voice. Marlon Brando studied those hand gestures and mastered that voice for his role as Don Vito Corleone in The Godfather. BY LORENZO CARCATERRA

John DiFronzo (born December 13, 1928), known as John "No Nose" DiFronzo is an American mobster and the reputed current boss of the Chicago Outfit.
DiFronzo, a former enforcer and caporegime, first appeared in the criminal record in 1949. He got the nickname "No Nose" because he sliced off part of his nose while jumping through a window during a 1949 clothing store burglary. Reportedly, the police gave him back the missing part which was almost perfectly restored.[2] In 1950, DiFronzo served two years in prison for burglary.
Wikipedia

Louis Tom Dragna (July 18, 1920 - November 16, 2012) was a mobster and nephew of Jack Dragna and son of Tom Dragna.He was active in the Los Angeles crime family from the 1940s until the early 1980s. Louis Tom Dragna was born on July 18, 1920 in Los Angeles, California to father Tom Dragna. He has a younger brother, Frank Paul Dragna (nicknamed "Two Eyes" to distinguish him from his cousin who had the same name and had a glass eye).wikipedia

Thomas Cacciopoli (born September 5, 1949), also known as Tommy Sneakers and Cacci, is a high-ranking member of the Gambino crime family, holding the rank of caporegime in the Queens, New Jersey, and Westchester faction of the family.
After John Gotti became boss in December 1985, Cacciopoli became a made member in the crew led by Gotti's son, John "Junior" Gotti and brother Peter Gotti. When John Gotti went to prison in 1992 and Junior Gotti became acting boss, Cacciopoli became Junior's top protegee and bodyguard. Cacciopoli allegedly received his moniker "Tommy Twitch" because he suffered from case facial neuralgia, an uncontrollable muscle spasm condition
wikipedia

Michael DiLeonardo (born June 18, 1955) is a former Italian-American mobster turned government informant. He was a capo belonging to the Gambino family. In the early 2000s, DiLeonardo decided to cooperate with the FBI and managed to convict over 80 mobsters. He was temporarily in a witness protection program. Born in New York City, DiLeonardo grew up in Bensonhurst, Brooklyn. He lived there until 1998, when he moved to Eltingville, Staten Island. At age 10, DiLeonardo was scarred on the face by a dog attack, resulting in the nickname "Mikey Scars". His parents were second-generation immigrants, his father's parents immigrants from Bisacquino, Sicily. His mother was a seamstress and his father was a professional gambler. wikipedia

http://www.sj-r.com/x517526805/What-s-in-a-Mafia-nickname

What’s in a Mafia nickname?

https://nypost.com/2008/02/10/how-mobster-nicknames-get-made/

HOW MOBSTER NICKNAMES GET ‘MADE’

In Chicago, the big story was a funeral. The city was saying good-bye to the Dingbat. The "Dingbat" was John Oberta, his nickname derived from a comic strip. He was 29 at the time of his death. Like Taft he was a Republican politician, the 13th Ward Committeeman. Unlike Taft, he was a gangster. Oberta was a protégé of Big Tim Murphy, bootlegger and labor racketeer in the Back-of-the-Yards neighborhood. One morning Big Tim opened his front door and had his head blown off by a shotgun blast. A few months later, Dingbat married Big Tim’s widow. Now Dingbat was gone, too. He had been found shot dead in his car, along with his chauffeur, on a deserted road near Willow Springs. By 1930 the gangster funeral had become a familiar Chicago custom. Dingbat’s friends would not scrimp. “I’m giving him the same I gave Tim,” Mrs. Murphy Oberta told reporters. Dingbat was waked in his home on South Richmond Avenue. He lay in a $15,000 mahogany coffin with silver handles, under a blanket of orchids.
Chicago Tribune

Julian "Potatoes" Kaufman was a personal O'Banion friend who provided him with advice and direction in the North Side Gang's gambling operations. Kaufman whose nickname originated from a sideline in speculating on potatos futures,was the son of a millionaire commission broker.His disdain for the law struck him at the age of 13 when his mother got shot and killed by a gang of boy bandits in a robbery gone wrong.
By Rose Keefe

Jake Guzik. His nickname "Greasy thumb", was the result of him proverbially greasing the wheels (throwing money bribes) at many an official who tried to put a halt to Capone's organization.

Aglieri is special, very religious guy. At one time he was seen as the new boss of bosses.

Matthew Joseph "Matty the Horse" Ianniello (June 18, 1920 – August 15, 2012) was a New York mobster with the Genovese crime family who was once the acting boss of the Genovese Crime Family. During the 1960s and 1970s, Ianniello controlled the lucrative adult entertainment business that was then centered in the Times Square section of Manhattan. Ianniello allegedly got his nickname "Matty The Horse" in a youth baseball game. Ianniello was a gifted player with a hard swing. During one game, the opposing pitcher threw a hard pitch into the face of the batter. A fight erupted in which Ianniello knocked down the pitcher, who was older and taller than him. After this episode, someone remarked about Ianniello: "That boy is as strong as a horse. wikipedia

Tino "T" Fiumara (August 11, 1941 – September 16, 2010), also known as "The Greek", was a major figure in the Genovese crime family. Since the 1980s, he had been the leader of the Genovese New Jersey faction in northern New Jersey. After his final release from prison Fiumara lived on Long Island. Tino Fiumara was born in Livingston, New Jersey to parents from Ali Superiore, Italy. His associates usually called him "T" or "the good-looking guy." Fiumara later earned the nickname "The Greek" from operating a crew in a Greek neighborhood of Bergen County, New Jersey.wikipedia

Stephen Armone (November 17, 1899 Palermo, Sicily – 1960), also known as "14th Street Steve", was a New York gangster with the Gambino crime family who ran gambling operations in Lower Manhattan. He was the older brother of Gambino capo Joseph Armone. Armone moved to the United States with his family to Queens. A small-statured man with black-gray hair, he limped due to a previous hip fracture. His arrest record included assault and battery with intent to kill, burglary, and narcotics laws violations. Armone was a leader of Gambino operations in the Lower East Side of Manhattan. He engaged in large-scale narcotics smuggling and distribution.wikipedia

Jack "Jack the Whack" Rizzocascio
This self-explanatory handle must be the ultimate clichéd gangster nickname.However, according to the FBI this mob moniker belongs to an associate of New York's Colombo crime family who was arrested.

Carmine Persico had a few "Junior", "The Snake", and "Immortal". I love the latter.

Ellsworth Raymond Johnson (October 31, 1905 – July 7, 1968) — known as "Bumpy" Johnson — was an African American mob boss and bookmaker in New York City's Harlem neighborhood. The main Harlem associate of the Luciano crime family, Johnson's criminal career has inspired films and television. Johnson was born in Charleston, South Carolina on October 31, 1905. Johnson derived his nickname "Bumpy" from a bump on the back of his head. After being released from prison in 1932, Johnson learned that notorious gangster Dutch Schultz, who was known as the Beer Baron of the Bronx, had moved in on the numbers racket in Harlem. Any numbers banker who refused to turn over his numbers operation to Schultz was targeted for violence. Schultz was murdered in 1935, which was arranged by Lucky Luciano and the National Crime Syndicate.
Luciano took over most of Schultz's number operations in Harlem but made a deal with Johnson which allowed the numbers bankers who had fought for their independence to remain independent as long as their operations participated in the Mafia's central gambling pool and Black operators tributes were paid. That deal made Johnson an instant hero in the eyes of many Harlemites, who were impressed that a black man could actually cut deals with the Italian Mafia.
Johnson was soon the toast of Harlem,and became friends with many Harlem luminaries such as Bill "Bojangles" Robinson, Ethel Waters, Cab Calloway, Lena Horne, Billie Holiday, and Sugar Ray Robinson. He also became the de facto crime boss of Harlem: no one could conduct criminal activities in his section of New York without first going through him. wikipedia

Frank Lucas (born September 9, 1930)is an American former drug trafficker, who operated in Harlem during the late 1960s and early 1970s. He was particularly known for cutting out middlemen in the drug trade and buying heroin directly from his source in the Golden Triangle. Lucas boasted that he smuggled heroin using the coffins of dead American servicemen,but this claim is denied by his South East Asian associate, Leslie "Ike" Atkinson. Rather than hide the drugs in the coffins, they were hidden in the pallets underneath as depicted in the 2007 feature film American Gangster in which he was played by Denzel Washington. Wiki pedia
Gave himself the nickname Superfly possibly inspired by the 1972 film Superfly, follows a character named Priest who is super slick,clever and crafty up and coming drug dealer.

James "Mad Bomber" Belcastro (1895 – August 23, 1945) was a Black Hand gang member, extortionist, and later chief bomber for the Chicago Outfit during Prohibition.
Known as "King of the Bombers", Belcastro was highly skilled at constructing improvised explosive devices. He used these skills to extort money from business owners in Chicago's Little Italy district during the 1910s. In the early 1920s, Johnny Torrio and Al Capone formed the Chicago Outfit and put the Black Hand gangs out of business. However, Capone invited Belcastro to join the Outfit and he soon became a prominent member. During the mid to late 1920s, Belcastro was suspected of causing over 100 deaths while bombing saloons that refused to buy alcohol from Capone. Wikipedia

Salvatore Joseph "Teets" Battaglia (November 5, 1908 – September 7, 1973) was a Chicago mobster and high-level member of the Chicago Outfit criminal organization.Battaglia was born in Chicago, Illinois. At age 16, Battaglia joined bosses Johnny Torrio and Al Capone in the Chicago Outfit at the start of the gang war against the mostly Irish North Side Gang, which was under boss Dean O'Banion. By the late 1930s, Battaglia had become a high-ranking member of the Outfit and a formidable loan shark.] Debtors behind in their payments would be brought to Battaglia in the back room of the Casa Madrid restaurant, in Chicago, where they would be severely beaten or killed. Supposedly Battaglia's nickname "Teets" came from one such encounter. Another mobster was questioning Battaglia's handling of a debtor and Battaglia yelled back at him, "Shaddup, or I'll bust ya in da teets! wikipedia

Benjamin Ruggiero, also known as "Lefty", "Lefty Guns", and "Lefty Two Guns", was a soldier in the Bonanno crime family. He is well known for his friendship and mentorship of FBI undercover agent Joseph "Donnie Brasco" Pistone.Wikipedia
He was given the nickname,Lefty, because when he shot dice, he always roll them with his left hand. The nickname, Two Guns, came from the observation that whenever he shot someone, he always did it with one gun in each hand. Keisha Joseph

Salvatore "Sally Dogs" Lombardi, uncle of Big Ang of Mob Wives, was low-key capo of the Genovese Crime Family. Even though he held the capo position within the highest profile criminal family in New York, Salvatore Lombardi is not very well known, publicly. He lived in Brooklyn and he and his crew members operated out of the Gravesend section. Big Ang says her uncle was like a bulldog that is why he was given the name”Sally Dogs”. Keisha Joseph & wikipedia

Tommaso "The Ox" Petto (1879–1905) was a New York mobster and leading hitman in the Morello crime family during the early 1900s.
Born around 1879, Petto lived in the Williamsburg section of Brooklyn. His nickname "The Ox" came from his massive head and frame. Petto's nominal profession was that of a suit presser, but his real job was working for the Morello family. The Morello family was a Sicilian clan in Manhattan that became infamous for killing their rivals, stuffing them in barrels, and leaving them on street corners.wikipedia

Carmine "Charley Wagons" Fatico (January 19, 1910 East New York, Brooklyn-August 1, 1991) was a Caporegime in the New York Gambino crime family. Fatico is best known as an early mentor to Gambino boss John Gotti. Fatico was a short, slim man known more for his intelligence than his physical power. However, Fatico did not shrink from brutal violence when he deemed it necessary. Fatico quickly became a leading capo in the Gambino family due to his unfailing loyalty and obedience, and his tireless and innovative ability to earn money. Fatico's nickname "Charley Wagons" alluded to his penchant for hijacking transport trucks. Carmine Fatico had a brother, Daniel Fatico, who was his partner in all his rackets.wikipedia

Alphonse "Allie Shades" Malangone (born December 2, 1936) is a New York City mobster and caporegime in the Genovese crime family, headed by Vincent Gigante. Malangone controlled the Genovese interests in the Fulton Fish Market, as well as being involved in pump and dump stock scams on Wall Street, and controlling Brooklyn's garbage hauling industry. He was a central figure in the book "Takedown: The Fall of the Last Mafia Empire" an autobiography by NYPD officer Rick Cowan who went undercover for several years in the commercial garbage industry, posing as a family member of Brooklyn garbage company and eventually gaining access to the garbage cartel's organization, he Kings County Trade Waste Association. ISBN 0-425-19299-7 Cowen describes Malangone as the cagiest and most relatable of mobsters he dealt with.
He got his nickname for always wearing aviator style tinted sunglasses, even at night.wikipedia