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Samuel "Red" Levine (December 27, 1902 – April 7, 1972) was an American mobster, described as head of Lucky Luciano's hit squad of Jewish gangsters. He was an observant Jew and refrained from killing on the Sabbath if possible. Levine was a member of Murder Inc, and is credited with being the trigger man in the 1931 murder of Joe "The Boss" Masseria, the old-school mobster who helped found America's Cosa Nostra. |  |
 | He was one of the hitmen along with Joe Adonis, Albert "Mad Hatter" Anastasia and Benjamin "Bugsy" Siegel sent by Meyer Lansky to assassinate the Sicilian Mafia boss Salvatore Maranzano. They managed to enter by posing as government agents. Once inside Maranzano's office on the 9th floor of The Helmsley Building, they disarmed the guards and shot and stabbed Maranzano to death. Murder Inc. was believed to be responsible for between 400 and 1,000 contract killings, until the group was exposed in the early 1940s by former group member Abe "Kid Twist" Reles. In the trials that followed, many members were convicted and executed, and Abe Reles himself died after suspiciously falling from a window while under police protection. |  |
 | Levine had a longstanding rivalry with fellow Murder Inc. hitman, Charles "The Bug" Workman. He was irritated that Workman took most of the murder contracts that would have otherwise gone to him. Levine once complained that "any time I've got a contract Charlie is around to do the killing." There is no mention of him when most of Murder Inc. and their surrounding factions were rounded up and successfully prosecuted. He simply faded away into the background and was not heard from again. |  |
 | Frank "The Irishman" Sheeran (October 25, 1920 – December 14, 2003) was a labor union official with links to the Bufalino crime family. As a high official in the International Brotherhood of Teamsters, Sheeran was a leading figure in the corruption of unions by organized crime. He was a trucker but made extra money on the side by committing crimes, including murder for hire. Sheeran is believed to have been behind 25 gangland slayings. Sheeran became a close associate of Mafia bosses Russell Bufalino and Angelo Bruno. It was Bufalino, the head of the Bufalino crime family, who acted as Sheeran's mentor throughout his life. |  |
 Hoffa at the Teamsters convention in 1957 | Bufalino set Sheeran up with the International President Jimmy Hoffa. Hoffa, who became a close friend, used Sheeran for muscle. Sheeran claimed to have been part of the provisioning of the anti-Fidel Castro forces involved in the Bay of Pigs invasion. The operation was a failed military invasion of Cuba undertaken by the CIA-sponsored paramilitary group Brigade 2506 on 17 April 1961. |  |
 | Sheeran also claimed to have intimate knowledge about the assassination of President John F. Kennedy. According to Sheeran, Jimmy Hoffa wanted Kennedy dead because Kennedy's brother Bobby Kennedy was harassing him. Shortly before his death, Sheeran claimed to have killed Jimmy Hoffa. Frank 'The Irishman' Sheeran |  |
 | Sheeran died of cancer on December 14, 2003, aged 83. |  |
 | John Herbert Dillinger, Jr. (June 22, 1903 – July 22, 1934) was an American bank robber. He was charged with, but never convicted of, the murder of an East Chicago, Indiana police officer during a shoot-out. This was his only alleged homicide. His gang robbed two dozen banks and four police stations. Dillinger escaped from jail twice and became a driving reason for the creation of the FBI. In the heyday of the Depression-era outlaw, Dillinger was the most notorious of them all. Dillinger is known to have participated with The Dillinger Gang in twelve separate bank robberies between June 1933 and June 1934. |  |
 | Dillinger was imprisoned at the Crown Point jail after committing a robbery at a bank in East Chicago on January 15, 1934. Police boasted to area newspapers that the Crown Point jail was escape-proof and posted extra guards to make sure. Dillinger escaped on March 3 using a fake gun carved with a razor made from some shelving in his cell. |   John Dillinger's Wooden Gun. Sold at Heritage Auction Galleries for $19,120.00 |
 | Three days after Dillinger's escape from Crown Point, he robbed a bank in Sioux Falls, South Dakota. By July 1934, Dillinger had dropped out of sight, and federal agents had no solid leads. He had drifted into Chicago where he went under the alias of Jimmy Lawrence, a petty criminal who bore a close resemblance to him. Division of Investigations chief J. Edgar Hoover created a special task force headquartered in Chicago to locate Dillinger. On July 21 a madam from a brothel in Gary, Indiana, Ana Cumpănaş, also known as Anna Sage, contacted the police. She was a Romanian immigrant threatened with deportation and offered the federal agency information on Dillinger in exchange for their help in preventing her deportation. |  |
 | Dillinger attended the film Manhattan Melodrama at the Biograph Theater in Chicago's Lincoln Park neighborhood. Dillinger was with Ana Cumpănaş. (Who was wearing a red dress to identify herself to agents.) When the movie let out, Special Agent Melvin Purvis stood by the front door and signaled Dillinger's exit by lighting a cigar. |  |
 | Both he and the other agents reported that Dillinger turned his head and looked directly at the agent as he walked by, glanced across the street, then moved ahead of his female companions, reached into his pocket and ran toward a nearby alley. Dillinger ignored a command to surrender, then headed for the alley. Agents already had the alley closed off. Agents Cowley, Charles Winstead, and Herman "Ed" Hollis opened fire, firing five shots. Dillinger was hit from behind and he fell face first to the ground. |  Dillinger was struck three times, with two bullets entering the chest, one nicking his heart, and the fatal shot, which entered the back of his neck and exited just under his right eye. |
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 | Pablo Emilio Escobar Gaviria (December 1, 1949 – December 2, 1993) was a Colombian drug lord and Medellín cartel leader. One of the wealthiest men in the world at the height of his power, the Medellín drug cartel was smuggling 15 tons of cocaine a day, worth more than half a billion dollars, into the United States. |  |
 | In the early 1970s Escobar was a thief and bodyguard. He made a quick $100,000 from the kidnapping and ransoming a Medellín executive before entering the drug trade with Alvaro Prieto. In 1975, Escobar started developing his own cocaine operation. He even flew a plane himself, mainly between Colombia and Panama, to smuggle a load into the United States. When he later bought 15 new and bigger airplanes (including a Learjet) and 6 helicopters, he decommissioned the plane and hung it above the gate to his ranch. |  |
 |  Pablo Escobar's party palace on a remote island off the coast of Cartagena on La Isla |  Vacation house in Guatape |
 | Corruption and intimidation characterized Escobar's operations. His policy in dealing with law enforcement and the government was referred to as "plata o plomo," (literally silver or lead, colloquially [accept] money or [face] bullets). This resulted in the deaths of thousands, including civilians, policemen and state officials. The Colombian cartels' continuing struggles to maintain control resulted in Colombia quickly becoming the world’s murder capital. In 1989, Forbes magazine estimated Escobar to be the seventh-richest man in the world with a personal wealth of close to US$25 billion while his Medellín cartel controlled 80% of the global cocaine market |
  | In 1992 United States Operators from Delta Force, Navy SEALs and Centra Spike joined an all-out manhunt for Escobar. They trained and advised a special Colombian police task force, known as the Search Bloc, which had been created to locate Escobar. The war against Escobar ended on December 2, 1993. Using radio triangulation technology provided by the United States, a Colombian electronic surveillance team found him hiding in a middle-class barrio in Medellín. A firefight with Escobar and his bodyguard ensued. The two fugitives attempted to escape by running across the roofs of adjoining houses to reach a back street, but both were shot and killed. |   |
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 | Last year Pablo Escobar’s once-opulent Colombian vacation home was demolished, 22 years after the drug lord’s death. The 20-room mansion, complete with a private runway for Escobar’s planes, was one of the main tourist draws at a theme park that now covers much of the drug dealer’s former estate of Hacienda Napoles. Theme park managers demolished the semi-ruined mansion before it collapsed. |  |
 | A herd of 50 hippos, the offspring of four animals bought in the 1980s for Escobar’s personal zoo, still roam the area. There’s also a former bullring. |  |
 | Vincent Louis Gigante (March 29, 1928 – December 19, 2005), also known as "Chin", was a New York Italian-American mobster in the American Mafia who was boss of the Genovese crime family from 1981 to 2005. Gigante started out as a professional boxer who fought 25 bouts between 1944 and 1947. Gigante won 21 of his 25 fights. He then started working as a Mafia enforcer for what was then the Luciano crime family. Gigante was one of five brothers: Mario, Pasquale and Ralph all became mobsters in the Genovese family. Only one brother, Louis, stayed out of the crime family, instead becoming a priest. |  |
 | Gigante was the shooter in the failed assassination of Frank Costello in 1957. After sharing a prison cell with Boss Vito Genovese following his conviction for heroin trafficking, Gigante became a caporegime, overseeing his own crew of Genovese soldiers and associates that operated out of Greenwich Village. Gigante was one of Genovese's most loyal supporters, siding with him throughout the struggle for power with Costello/Luciano/Anastasia. |  Boss Vito Genovese |
  | Gigante quickly rose to power during the 1960s and 1970s. By 1981 he became the family's boss, while Anthony "Fat Tony" Salerno served as front boss during the first half of the 1980s. He also ordered the failed murder attempt of Gambino crime family boss John Gotti in 1986. With the arrest and conviction of Gotti and various Gambino family members in 1992, Gigante was officially recognized as the most powerful crime boss in the United States. |  |
 | Dubbed "The Enigma in the Bathrobe" or "The Oddfather", Gigante often wandered the streets of Greenwich Village in his bathrobe and slippers, mumbling incoherently to himself. After he successfully averted prison in the late '60s by employing psychiatrists to testify to his insanity, he continued the act. |  |
 | In 1990, Gigante was arrested and charged with racketeering and murder; however, it wasn't until 1997 that he was brought to trial. During that time period, Gigante's lawyers produced witness after witness who testified that Gigante was mentally ill and unfit to stand trial. The delay allowed Gigante's legal team to use the "windows racket" case as a preview of the government's case against Gigante. However, this gambit backfired when four high-ranking members of other families began to cooperate with the government in the early 1990s. |  |
  | In 1997, Gigante was convicted on racketeering and conspiracy charges and sentenced to 12 years in a federal prison. Gigante retained control of the crime family and relayed orders through his son, Andrew, who would visit him in prison. |  |
 | In 2005, Gigante's health started to decline. He suffered labored breathing, oxygen deprivation, swelling in the lower body, and bouts of unconsciousness. On December 19, 2005 he died. |  Philip Gigante, the mayor of Airmont, NY, is the grandson of the late Genovese crime-family godfather Vincent “The Chin” Gigante |
Al Capone
 | Alphonse Gabriel "Al" Capone (January 17, 1899 – January 25, 1947) was an Italian-American gangster who led a Prohibition-era crime syndicate in Chicago from the early 1920s to 1931. Bootlegging, smuggling and prostitution made Capone millions. |  |
Capone was widely seen as the man responsible for ordering the Saint Valentine's Day Massacre, when seven rival gang members were executed in the Lincoln Park neighborhood on Chicago's North Side in 1929.  |  |  The victims were executed in a garage at 2122 North Clark Street. (then SMC Cartage Co.) |
 |  Capone's mug shot in 1933  Weapons used in Saint Valentine's Day Massacre |  |
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 | Capone was convicted on federal charges of tax evasion, and sentenced to federal prison. His term included time at the then-new Alcatraz federal prison. In the final years of Capone's life, he suffered mental and physical deterioration due to late-stage neurosyphilis, which he had contracted in his youth. On January 25, 1947, he died from cardiac arrest after suffering a stroke. |  |
 Al Capone en route to prison in 1931 |  Prisoner #85: Al Capone's booking mugshot at Alcatraz Federal Penitentiary |  |
 | Dutch Schultz (born Arthur Flegenheimer; August 6, 1902 – October 24, 1935) was a New York City-area Jewish American gangster who made his fortune in organized crime-related activities such as bootlegging, loan sharking and the numbers racket. Along with other rackets, Schultz began extorting New York restaurant owners and workers. Those gangsters who skimmed the take did not last long. |  |
 | "Dutch Schultz was ugly; he had been drinking and suddenly he had his gun out. Schultz wore his pistol under his vest, tucked inside his pants, right against his belly. One jerk at his vest and he had it in his hand. All in the same quick motion he swung it up, stuck it in Jules Martin's mouth and pulled the trigger. It was as simple and undramatic as that—just one quick motion of the hand. Dutch Schultz did that murder just as casually as if he were picking his teeth.” | 
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 | As Martin contorted on the floor, Schultz apologized to Davis for killing someone in front of him. When Davis later read a newspaper story about Martin's murder, he was shocked to find out that the body was found on a snow bank with a dozen stab wounds to the chest. When Davis asked Schultz about this, the boss dead-panned, "I cut his heart out." At the time of the Martin killing, Schultz was fighting a federal tax evasion case: U.S. Attorney Thomas Dewey had set his sights on convicting Schultz. Schultz was convicted of the charges, but they were soon overturned. |  |
 Dutch Schultz at the N.Y. Courthouse in 1935. | Schultz went before the Mafia Commission and asked permission to kill Dewey. All were against it because the full weight of the law would come down on them. Schultz was furious at the outcome of the vote; he accused the Commission of trying to steal his rackets and "feed him to the law." After Schultz left in a rage, the Commission decided to kill him. Albert Anastasia sent Jewish mobster Louis Buchalter. |  Bonanno family boss Joseph Bonanno thought the idea was "insane." |
  | At 10:15 p.m. on October 23, 1935, Schultz was shot multiple times at the Palace Chophouse at 12 East Park Street in Newark, New Jersey. Doctors performed surgery but were unaware of the extent of damage done to his abdominal organs by a ricocheting bullet. They were also unaware that the gunmen had intentionally used rust-coated bullets in an attempt to give Schultz a fatal bloodstream infection (septicemia) should he survive the gunshot. Schultz lingered for 22 hours before dying of peritonitis. Two bodyguards and Schultz's accountant were also killed.  |   |
 | Though estimated to be worth over $7 million (128m in 2017 dollars) when he died, no trace of his wealth has ever been found. It is thought Schultz hid his treasure in a safe somewhere in the Catskill Mountain range. The story says he stashed away millions somewhere in the heavily forested area of Phoenicia, New York. When Schultz was gunned down in 1935, the location of his vast fortune died with him. |  |
 | Benjamin "Bugsy" Siegel (born Benjamin Siegelbaum February 28, 1906 – June 20, 1947) was an American gangster who was an associate of the Genovese crime family. Siegel was a driving force behind development of Las Vegas as a gambling mecca.  |  |
  | Bugsy Siegel was a textbook sociopath and murderer many times over. Ruthless and cold blooded, remorse was alien to him. In gangster circles, the nickname "Bugsy" is often a term of endearment or honor. It is given out to those racketeers who show no fear. Siegel was quoted as saying "My friends call me Ben, strangers call me Mr. Siegel, and guys I don't like call me Bugsy, but not to my face."  |   |
 | In 1937, the East Coast mob sent Siegel to California to develop syndicate gambling rackets with Los Angeles crime family boss, Jack Dragna. Using investments from the mob, he took over the plans to build the first casino resort in Vegas. The project ran far over budget as no expense was spared. The mob was not happy, as they had already put a massive 5 million dollars into the project. By early November 1946 The syndicate had had enough. |  |
 | On the night of June 20, 1947, as Siegel sat with his associate Allen Smiley in Virginia Hill's Beverly Hills home reading the Los Angeles Times, an unknown assailant fired at him through the window with a .30-caliber military M1 carbine, hitting him many times, including twice in the head. No one was charged with the murder, and the crime remains officially unsolved. |  |
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 | Charles Arthur "Pretty Boy" Floyd (February 3, 1904 – October 22, 1934) was an American bank robber. When paroled after his first bank robbery Floyd vowed that he would never see the inside of another prison. He committed a series of bank robberies over the next several years; it was during this period that he acquired the nickname "Pretty Boy." According to one account, when the payroll master targeted in a robbery described the three perpetrators to the police, he referred to Floyd as "a mere boy — a pretty boy with apple cheeks." |  |
 | "Pretty Boy" Floyd and Adam Richetti became the primary suspects in a June 17, 1933, gunfight known as the "Kansas City massacre" that resulted in the deaths of four law enforcement officers. |  |
 | On October 22, 1934, Floyd was killed in an apple orchard near East Liverpool, Ohio, while being pursued by local law officers and FBI agents led by Melvin Purvis. He hated his nick name so much that after being gunned down, with his dying breath he made one final declaration, “I’m Charles Arthur Floyd.” |  Broken Thompson that Floyd had abandoned. |
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 | John Joseph Gotti, Jr (October 27, 1940 – June 10, 2002) was an American mobster who became the Boss of the Gambino crime family in New York. Gotti quickly rose in prominence in the Gambino ranks, becoming one of the crime family's biggest earners. Gotti became a protege of Gambino family underboss Aniello Dellacroce.  |   |
 | Fearing he would be killed by Gambino crime family Boss Paul Castellano for selling drugs, Gotti organized the murder of Castellano in December 1985 and took over the family shortly thereafter. This left Gotti as the boss of the most powerful crime family in America, which made hundreds of millions of dollars a year from construction, hijacking, loan sharking, gambling, extortion and other criminal activities. |  |
 | Gotti survived numerous legal cases unscathed. Witnesses developed serious cases of what the press called "I forgotti", and with every acquittal it added to his reputation. The American media dubbed Gotti "The Teflon Don" due to the failure of any charges to "stick." On December 11, 1990, FBI agents and New York City detectives raided the Ravenite Social Club, arresting Gotti, Gravano and Frank Locascio. Gotti was charged, in this new racketeering case, with five murders (Castellano and Bilotti, Robert DiBernardo, Liborio Milito and Louis Dibono,) conspiracy to murder Gaetano "Corky" Vastola, loansharking, illegal gambling, obstruction of justice, bribery and tax evasion. Sammy Gravano opted to turn state's evidence, formally agreeing to testify on November 13, 1991. |  |
 | On April 2, 1992, the jury found Gotti guilty on all charges of the indictment. He was sentenced to life imprisonment without the possibility of parole and a $250,000 fine.  |  |
 | Antonino Joseph Accardo (April 28, 1906 – May 22, 1992), also known as "Joe Batters" or "Big Tuna", rose from small-time hoodlum to the position of boss of the Chicago Outfit in 1947. Ultimately he became the final Outfit authority by 1972. Accardo moved The Outfit into new operations and territories, greatly increasing its power and wealth during his tenure as boss. In 1929, Capone was convicted of tax evasion and sent to prison for an 11-year sentence, and Frank "The Enforcer" Nitti became the new Outfit boss, after serving his own 18-month sentence for tax evasion. |  |
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 | Accardo soon developed a wide range of profitable rackets, including gambling, loansharking, bookmaking, extortion, and the distribution of untaxed alcohol and cigarettes. As with all caporegimes, Accardo received 5% of the crew's earnings as a so-called, "street tax." Accardo in turn paid a tax to the family boss. If a crew member were to refuse to pay a street tax (or paid less than half of the amount owed), it often meant a death sentence. |  |
 | After Nitti committed suicide in 1943, Paul "The Waiter" Ricca, who had been the de facto boss since Capone's imprisonment, became the boss and named Accardo as underboss. Ricca and Accardo would run the Outfit either officially or as the powers behind the throne for the next 30 years, until Ricca's death in 1972. By keeping a low profile and letting flashier figures such as Sam Giancana attract attention, Accardo and Ricca were able to run the Outfit much longer than Capone. Ricca once said, "Accardo had more brains for breakfast than Capone had in a lifetime." |  |
 | In his later years, Accardo spent much of his time in Palm Springs, California, flying to Chicago to preside over Outfit "sit-downs" and mediate disputes. Accardo's personal holdings included legal investments in commercial office buildings, retail centers, lumber farms, paper factories, hotels, car dealerships, trucking companies, newspaper companies, restaurants and travel agencies. Accardo spent his last years in Barrington Hills, Illinois living with his daughter and son-in-law. On May 22, 1992, Anthony Accardo died of congestive heart failure at age 86. Despite an arrest record dating back to 1922, Accardo spent only one night of his life in jail. |  |
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