Top 10 Gangsters Who Ratted On Their Own Organizations

#10: Max Mermelstein

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Medellín Cartel (1985) Florida-based engineer and smuggler Max Mermelstein was a key player in the Medellín Cartel's American operations. After his arrest in 1985, he provided one of the U.S. government’s first major blows against the organization. Mermelstein’s testimony brought indictments against Pablo Escobar, Fabio Ochoa Vásquez, and others. At the time, he was the most valuable informant in American history. Escobar put out a $3 million bounty for Mermelstein, who was protected by the Witness Protection Program. Mermelstein was still under protection when he died of cancer 15 years after the cartel's dissolution. Betraying the world’s most notorious drug syndicate cost him his family and his very identity. This sacrifice surely wasn't the worst decision of his life.

Bonnano Crime Family (2004) Joseph Massino turned the Bonanno Family into the most powerful mafia of the new millennium. He was so scrupulous that he ordered colleagues to refer to him by tugging their ears, in case the FBI was bugging their meetings. But with made men naming him in a RICO case in 2004, “The Ear” was facing the death penalty. He thus became the first boss in the history of New York’s Five Families to turn state’s evidence. Of course, Massino didn’t testify until 2011, when he aided in the conviction of his successor Vincent Basciano. Following another testimony, his life sentence was reduced to time served in 2013. The so-called “Last Don” lived the last decade of his life as a free man.

Genovese Crime Family (1963) Though the Italian-American Mafia hid in plain sight, the code of omertà forbade members from so much as acknowledging its existence. Joseph Valachi set the record straight in 1963. When the Genovese grunt was suspected of ratting in prison, he killed an inmate erroneously believed to be a hitman. This ironically put Valachi at the mercy of federal authorities. It’s uncertain if he turned informant strictly out of self-preservation or genuine disillusionment. Either way, the televised “Valachi Hearings” revealed the inner workings of the Cosa Nostra. Valachi did not directly implicate any colleagues, but provided law enforcement with unprecedented intel in their war on organized crime. He lived the rest of his life and wrote his memoirs in the security of a Texas prison.

Gambino Crime Family (2002) During the Gambino Family’s restructuring after John Gotti’s conviction, Michael DiLeonardo was made a captain. He became a top earner in the Gottis’ inner circle, until both the feds and the family charged him with being a crook. DiLeonardo decided to take some men down with him. He testified in court 15 times, more than any made man in Mafia history. This led to some 80 convictions, including several of the Gottis and their closest associates. He even directly implicated the heads of the Colombo Family. DiLeonardo is further distinguished by his personal honesty. In interviews, he recognizes his courageous testimony as an act of betrayal and weakness. At least DiLeonardo walks free, albeit in Witness Protection.

#6: Abe "Kid Twist" Reles

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Murder, Inc. (1940) The contract syndicate Murder, Inc., was a favorite among American gangs in need of a hitman. Abe Reles himself could use an ice pick to simulate a cerebral hemorrhage. When the law finally caught up with him in 1940, he adopted a different method of execution. Reles testified against many of his fellow hitmen and their clients, some of whom received the death penalty. After being scheduled to testify against the Gambino Family, Reles fell to his death from a hotel window while under police protection. A grand jury’s conclusion that he was attempting to escape is still in question.

#5: Henry Hill

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Lucchese Crime Family (1980) Despite being barred from official membership because of his Irish heritage, Henry Hill was a close associate of the Lucchese Crime Family. This made him a great asset after his arrest for drug trafficking in 1980. Already concerned that he was marked for death, Hill provided the FBI with extensive evidence and testimony. He ensured 50 convictions, then spent the next seven years moving around the U.S. in Witness Protection. But the whole world would remember this low-level mobster’s name. Hill’s story was the focus of the bestselling book “Wiseguy” and Martin Scorsese’s “Goodfellas,” one of the most popular gangster films ever made. Hill finally became big time, though was not respected for it.

#4: James "Whitey" Bulger

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Walter Hill Gang (1975) The brutal leader of the Winter Hill Gang openly terrorized Boston for years. How did he get away with it for so long? In 1975, James “Whitey” Bulger agreed to become an FBI informant without facing criminal charges. This allowed him to cripple rival gangs, while protecting his own from the authorities. But in 1994, public exposure of this corrupt deal forced Whitey to go on the run. He was captured in 2011, and ultimately convicted on 31 counts. One of the FBI’s highest assets ended up being one of their most notorious fugitives ever. The cold-blooded Bulger never ratted on himself, though. In 2018, the 89-year-old was beaten to death in prison.

#3: Frank Lucas

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Independent (1976) With the Mafia controlling New York's narcotics market, Frank Lucas was an industry unto himself. The kingpin was known for personally smuggling his product from the Golden Triangle. Still, for all his power and elusiveness, Lucas was sentenced to 70 years for trafficking in 1976. He soon turned on his colleagues. By the time his sentence was reduced to time served in ‘81, Lucas was responsible for more than 100 convictions. He was himself convicted of dealing again three years later. Lucas’s story as criminal underdog and rat is truly one-of-a-kind. Denzel Washington immortalized him in pop culture in the acclaimed film “American Gangster,” but Lucas’s significance on both sides of the war on drugs goes beyond cinematic.

Sicilian Mafia (1984) Dubbed “The Boss of Two Worlds,” Tommaso Buscetta was indispensable in the Sicilian Mafia’s U.S. and Brazilian operations. He remained loyal throughout a ten-year sentence. But with a gang war that claimed several loved ones, he became disillusioned. In 1984, Buscetta began informing Italian and American authorities of the Cosa Nostra's inner workings. He testified during the historic Maxi Trial, and was spurred by an assassination attempt to expose political ties. This led to nearly 400 convictions that devastated an international criminal empire. A story this cinematic naturally inspired a hit biopic in 2019’s “The Traitor.” Though Buscetta spent most of his life in hiding, perhaps that sacrifice atoned for some of his earlier crimes.

Gambino Crime Family (1991) John Gotti led the Gambino Family as one of the most powerful and ruthless figures in modern organized crime. He couldn’t have done it without Sammy Gravano’s often brutal support. But after the Gambino leader’s arrest in a raid, the FBI revealed wiretap recordings of Gotti questioning his underboss’s integrity. This convinced “The Bull” to become the first high-ranking New York mafioso to turn state’s evidence. His testimony sealed the Teflon Don’s conviction on 13 counts in 1992. Galvano later was busted as part of a drug ring. By the time he left prison again in 2017, interviews and a biography had made him a celebrity. He is now a legit public figure, showing that there is life after bringing down the toughest gangsters. What are your favorite stories of gangland treachery? Tell all in the comments.