Mobsters and mouthpieces, snitches and stool pigeons…history is a graveyard of colorful and controversial gangland prosecutions, and these are my candidates for the all-time Top Ten:

10. Waxey Gordon (1933). After a painstaking investigation that included over 200,000 deposit slips, 100,000 telephone records, and a thousand witness interviews, New York’s “boy prosecutor,” Thomas E. Dewey, 31, overcame bribed and vanished witnesses to convict bootlegger Irving “Waxey Gordon” Wexler, 45, of having paid less than $100 in taxes on income of more than $4.5 million from his vast empire of breweries and speakeasies

9. Whitey Bulger (2013). The leader of South Boston’s murderous Winter Hill Gang and a long-time FBI informant, James “Whitey” Bulger, Jr., spent 16 years on the lam from a RICO indictment before his 2011 arrest in California. Bulger, 84, was eventually found guilty on thirty-one racketeering counts that included complicity in eleven murders.

8. Dutch Schultz (1935). Bootlegger and numbers racketeer Arthur “Dutch Schultz” Flegenheimer twice stood trial for income tax fraud. After the first trial resulted in a hung jury, his second trial, held in Malone, New York, in July of 1935, ended in a sensational acquittal when jurors accepted the Dutchman’s defense that he’d received bad legal advice. Returning triumphant to his native Bronx, Flegenheimer, 36, began planning the murder of prosecutor Thomas Dewey but, before he could act, was himself gunned down on October 23, 1935, inside the Palace Chop House in Newark, New Jersey.

7. John Gotti (1992). Boss of New York’s Gambino crime family, the ever-dapper John J. Gotti, 52, the so-called Teflon Don, was convicted on fifteen counts of murder, racketeering, and obstruction of justice thanks to the testimony of underboss-turned-FBI informant Salvatore “Sammy the Bull” Gravano.

6. The Pizza Connection (1985-87). The culmination of a multi-year international drug-smuggling investigation, the so-called Pizza Connection trial of Sicilian mob boss Gaetano Badalamenti, 64, and 21 codefendants lasted 18 months and featured the testimony of FBI Special Agent Joseph (“Donnie Brasco”) Pistone. Lead investigator Louis J. Freeh would later become Director of the FBI.

5. The Chicago Outfit (1943-44). With Johnny Torrio retired and Al Capone medically incapacitated, mob boss Frank Nitti, 57, expanded the Chicago Outfit’s union influence all the way to Hollywood before informants Willie Bioff and George Browne blew the whistle on the Mafia’s widespread extortion of the American film industry. While Nitti committed suicide before the trial began, seven of his top lieutenants, including Paul Ricca and Johnny Rosselli, were convicted and sentenced to 10-year terms.

4. The Maxi Trial (1986-87). An adjunct to the more famous Pizza Connection drug-smuggling trial in New York, the so-called Maxiprocesso trial in Palermo, Sicily, was the largest and most expensive prosecution in world history. It resulted in the conviction of 338 defendants (including Sicilian Mafia boss Michele “the Pope” Greco), the imposition of a collective 2665 years in jail sentences, and fines totaling almost $10 million.

3. The Mafia Commission (1986). In a massive investigation targeting the heads of New York’s Five Families, FBI agents working under U.S. Attorney Rudolph Giuliani, 42, employed extensive wiretaps to indict eleven of the biggest names in organized crime. Eight defendants, including Anthony “Fat Tony” Salerno, Carmine “Junior” Persico, and Anthony “Tony Ducks” Corallo, were eventually found guilty on 151 RICO counts and received sentences of up to 100 years each. The case launched the political careers of both Giuliani, who became mayor of New York City, and lead prosecutor Michael Chertoff, who later headed the U.S. Department of Homeland Security.

2. Lucky Luciano (1936). Dubbed “The Man Who Organized Crime in America,” Salvatore “Lucky Luciano” Lucania, 38, was indicted on ninety counts of compulsory prostitution after special prosecutor Thomas Dewey arrested over eighty New York madams and prostitutes and held them as material witnesses for up to four months before trial. Thanks to the testimony of star witness “Cokey Flo” Brown, Lucania and eight codefendants were each found guilty on sixty-two counts, burnishing the crime-busting credentials that would carry Dewey, 34, to the New York governor’s mansion and almost to the White House.

  1. Al Capone (1931). The tax-evasion prosecution of Chicago bootlegger and mob boss Alphonse “Scarface” Capone, 33, by U.S. Attorney George E. Q. Johnson was the culmination of years of exhaustive investigations conducted by U.S. Prohibition Agent Eliot Ness and U.S. Treasury Agent Frank Wilson. Convicted on five of the indictment’s twenty-three counts, Capone would serve fewer than 8 years of his 11-year sentence, but his trial would serve as a blueprint for virtually every mob prosecution that followed.

Joseph Greaves is the award-winning author of five novels, most recently Tom & Lucky and George & Cokey Flo (Bloomsbury), a novelization of the Luciano vice trial. You can visit him at