Born in New York in 1928, Vincent Gigante was quite a character. He dropped out of high school in the ninth grade and started boxing, winning 21 of 25 light-heavyweight bouts. By the time he was 17, he had turned to crime to support himself, which resulted in seven arrests before he was 25.
Gigante’s first significant act as a gangster and member of the Genovese family was an attempt to kill the powerful Frank Costello, but Gigante’s bullet missed the target. Nevertheless, he continued to climb the ranks within New York’s Genovese organization, eventually becoming a capo and consigliere in the early ’80s.
Then, when Mob boss Tony Salerno was convicted, Gigante became the main man. What makes Gigante so memorable is his 30-year ploy of acting insane. After he successfully averted prison in the late ’60s by employing psychiatrists to testify to his insanity, he took it upon himself to continue the act; throughout his career, he was often seen walking around the streets of New York wearing a bathrobe. For this reason, he was nicknamed the “Oddfather” and the “Pajama King.” Imprisoned for racketeering, he finally admitted in 2003 that he was not crazy.
Gigante died in prison on December 19, 2005 due to heart complications. The Gigante family and his lawyer, Flora Edwards, filed a federal lawsuit regarding the lack of health care that Vincent received while in prison. Vincent was scheduled for release in 2010.
Featured in: Gigante was a character in the made-for-TV film Bonanno: A Godfather’s Story (1999) and served as inspiration for an episode of Law & Order.
Born in Tropea, Italy in 1903, Albert Anastasia was still a teenager when he came to America. Involved in the docks operations in Brooklyn, Anastasia was sent to Sing Sing Prison for 18 months for the murder of a longshoreman; the mysterious deaths of witnesses led to his early release. Albert Anastasia (aka “Lord High Executioner” and “Mad Hatter”) was known as a killer, a reputation that led Joe Masseria’s gang to recruit him. Anastasia was also extremely loyal to Charles “Lucky” Luciano, who had plans to rule America’s crime world. Anastasia had no problem betraying Masseria — by being one of four people sent to kill him in 1931 — when approached by Lucky Luciano.
At this time, Anastasia started taking on hits for the Murder, Incorporated outfit in New York, and in 1944, he became the leader of the murder squad. Although Anastasia was never prosecuted for any killings, Murder, Inc. was responsible for between 400 and 700 murders. In the ’50s, he became the leader of the Luciano family, but Carlo Gambino wanted the job. Though the murder is officially unsolved, many believe that Gambino had Anastasia killed in a barbershop in 1957.
Featured in: Albert Anastasia was a prominent character in Murder, Inc. (1960), a gangster film starring Peter Falk and Howard Smith (as Anastasia), as well as in The Valachi Papers (1972) and Lepke (1975).
From Joey Bananas to John Gotti, check out the other gangsters who were a hit…
Born in 1905, Joe Bonanno grew up in his native Sicily and became an orphan at the age of 15. He left Italy due to the fascist power of the Mussolini regime and made a brief stopover in Cuba before moving to the United States when he was 19. Joe joined the Mafia as a way to prevent Mussolini from taking over Sicily. Nicknamed “Joey Bananas,” he joined forces with Salvatore Maranzano. Before Luciano killed him, Maranzano created The Commission, the ruling body over Mafia families in the entire country.
Bonanno stepped up and took over one of these families. He became powerful in New York with cheese factories, clothing businesses and funeral homes, which were a terrific way to dispose of bodies. But plans to eliminate all the rival families turned against him and Bonanno was kidnapped for 19 days until he agreed to retire. In 1965, he initiated the Banana War to settle scores, but he retired for good soon thereafter due to bad health. Never in his life was he convicted of a serious offense.
Featured in: Two cable movies have been made about the crime legend: Love, Honor & Obey: The Last Mafia Marriage (1993) with Ben Gazzara and Bonanno: A Godfather’s Story (1999) with Martin Landau.
Arthur Flegenheimer, later known as Dutch Schultz, was born in the Bronx in 1902. As a teenager, he held up crap games to impress his boss and mentor, Marcel Poffo. At the age of 17, he did some time at Blackwell’s Island (now known as Roosevelt Island) for theft. With prohibition in full swing in the 1920s, he realized that money was in bootlegging. A ruthless man, he would kill whenever his temper flared, which helped keep his competition in line.
He had a part in the founding of the Syndicate, but soon Luciano and Capone became his enemies. In 1933, the law wanted to shut down Schultz, so he went into hiding in New Jersey, which left his New York territory free for a takeover; Luciano seized the opportunity. Schultz made a comeback in 1935, but members of Albert Anastasia’s crew killed him in a restaurant men’s room before he could do any damage.
Featured in: Dustin Hoffman was memorable as Dutch Schultz in Billy Bathgate (1991), but Tim Roth was even better in Hoodlum (1997). Other movies featuring Schultz include Gangster Wars (1981), The Cotton Club (1984) and The Natural (1984).
In the wake of the great gangsters who ruled New York, John Gotti had his work cut out for him. Born in Brooklyn in 1940, he was always quick with his fists and it was his life’s dream to become a wiseguy. By the age of 16, he had joined a local street gang known as the Fulton-Rockaway Boys. He quickly became their leader, stealing cars and fencing stolen goods. In the ’60s, he began associating with Mafia hoods and hijacking trucks. In the early ’70s, he became a capo for the Bergin crew, a part of the Gambino family. Extremely ambitious, Gotti started to deal drugs, which was forbidden by family rules.
As a result, Paul Castellano, the Boss, wished to expel Gotti from the organization. In 1985, Gotti and his guys killed Castellano outside a steakhouse and Gotti took over the Gambino family. No matter how many times the authorities tried to indict him for being the most powerful criminal in New York, the charges were always dropped. Because of this — and the fact that he dressed well and loved media attention — he was nicknamed “The Dapper Don” and “The Teflon Don.” He was finally convicted for murder in 1992 and died of cancer in prison in 2002.
Featured in: He was played by Anthony John Denison in the made-for-TV movie Getting Gotti (1994) and by Armand Assante in the HBO event Gotti (1996). Other TV movies featuring him include Witness to the Mob (1998) with Tom Sizemore and The Big Heist (2001).
Moving up the gangster ranks…
Born Maier Suchowljansky in Russia to Jewish parents in 1902, Lansky moved to New York when he was 9. He met Charles Luciano when they were just schoolboys. Luciano demanded protection money from Lansky, and when he refused to pay, the two boys fought. Impressed by Lansky’s toughness, Luciano befriended the younger boy and the two remained lifelong friends. Lansky also met Bugsy Siegel when he was a teenager, and the three formed a powerful partnership. Lansky and Siegel formed the Bug and Meyer Mob, which became Murder, Inc.
Lansky’s primary order of business was money and gambling, and he had operations in Florida, Cuba and New Orleans. He was an investor in Siegel’s Las Vegas casino, and he even bought an offshore bank in Switzerland that was used for money laundering. A financial genius, he codeveloped the National Crime Syndicate and the Commission. But business is never personal, and he approved the murder of his best friend Bugsy Siegel when Siegel was unable to produce profits for the Syndicate. Even with a gambling racket in operation across the planet, Lansky never spent a day in jail.
Featured in: Not only did Richard Dreyfuss give a powerful performance in HBO’s Lansky (1999), but the character of Hyman Roth in The Godfather Part II (1974) was loosely based on him as well. The role was also played by Mark Rydell in Havana (1990), Patrick Dempsey in Mobsters (1991) and Ben Kingsley in Bugsy (1991).
Francesco Castiglia was born in 1891 in Italy and moved to the United States with his family when he was 4. He changed his name to Frank Costello when he joined a street gang at age 13. After numerous petty crimes landed him in prison, he became best friends with Charlie Luciano; together, they dealt in bootlegging and gambling. Costello’s strength was his position as a link between the Mob and politicians, especially the Democratic Party’s Tammany Hall in New York, which enabled him and his associates to pay off certain officials.
Following Luciano’s arrest, Costello became the man in charge, and he solidified and expanded the operation during this time. A power struggle between him and Vito Genovese (who served as Underboss) erupted in the ’50s, and Vincent Gigante tried to kill Costello. Eventually, Costello grew tired of the gangster life and retired, but not before framing Genovese and Gigante for a drug bust. He died peacefully in 1973.
Featured in: The man was best portrayed by James Andronica in the 1981 miniseries The Gangster Chronicles, by Costas Mandylor in Mobsters (1991), by Carmine Caridi in Bugsy (1991), and by Jack Nicholson in The Departed (2006).
Carlo Gambino came from a family that had been part of the Mafia for centuries in Italy. He started carrying out murders when he was a teenager and became a made guy in 1921 at the age of 19. With Mussolini gaining power, he immigrated to America, where his cousin Paul Castellano lived. He became a thug for different New York families until he joined Lucky Luciano’s crew.
After Luciano was extradited in the ’40s, Albert Anastasia took over. But Gambino thought it was his time to shine and had Anastasia killed in 1957. He appointed himself Boss of the family and reigned with an iron fist over New York until his natural death in 1976.
Featured in: Al Ruscio played him beautifully in the TNT movie Boss of Bosses (2001). Other “Gambino” appearances include the made-for-TV movies Between Love & Honor (1995), Gotti (1996) and Bonanno: A Godfather’s Story (1999).
Check out the top two gangsters of all time and an honorable mention…
Salvatore Lucania was born in Sicily in 1897, but his family moved to New York nine years later. At a young age, he became a member of the Five Points gang, in which Al Capone also received his education. Five years after establishing an empire based mostly on prostitution, Luciano controlled the racket all over Manhattan. After a failed but brutal attack on his life in 1929, Luciano started planning the National Crime Syndicate, an extension of Salvatore Maranzano’s Commission, with Meyer Lansky.
They eliminated the competition, and by 1935, Lucky Luciano was known as the Boss of Bosses — not just of New York City, but of the whole country. He was arrested and sentenced to 30 to 50 years in 1936, but was let out on parole in 1946 on the condition that he be deported to Italy. He had so much power that U.S. Navy intelligence sought his help when the Allies were set to invade Italy during World War II. He died of a heart attack in 1962.
Featured in: Christian Slater played him in Mobsters (1991), as did Bill Graham in Bugsy (1991) and Anthony LaPaglia in the TV film Lansky (1999).
If there ever was a gangster who earned the No. 1 spot, it is Al Capone. Alphonse Capone was born in 1899 to Italian immigrants in Brooklyn, New York, where he got his start in street gangs. He then joined the Five Points gang and became a bouncer. It was during these days that a series of facial wounds earned him the “Scarface” nickname. Capone moved to Chicago in 1919 and quickly moved up the Mafia hierarchy while working for Johnny Torrio (Capone became Torrio’s protege).
It was the time of the Prohibition, and Capone ran prostitution, gambling and bootlegging rings. In 1925, at the age of 26, Capone took over after Torrio was wounded in a gang war. Known for his intelligence, flamboyance and love of public attention, Capone was also known to be very violent; his role in the orchestration of the St. Valentine’s Day Massacre in 1929, in which key rival gangsters were murdered, proves this. In 1931, Federal Treasury agent Eliot Ness arrested him for tax evasion.
Featured in: Many movies have been made about Capone, but the most famous are probably The St. Valentine’s Day Massacre (1967) with Jason Robards, Capone (1975) with Ben Gazzara and The Untouchables (1987) with Robert De Niro.