Allan May

Charlie "The Bug" Workman

The story of Charlie "The Bug" Workman, who was rumored to have killed 20 men. One of those 20 men was Dutch Schultz.

by Allan May

When I read the biographies of criminals in Jay Nash’s World Encyclopedia of Organized Crime and Carl Sifakis’s Mafia Encyclopedia, I was amazed at the number of murders attributed to certain mobsters. I sometimes think that if all these murders were really committed there wouldn’t be anyone left on the planet (a slight exaggeration).

One of the more prolific murderers was Charlie Workman, variously known as "The Bug," "The Powerhouse," and "Handsome Charlie." He was rumored to have dispatched 20 individuals.

"Mad Sam" DeStefano

The story of a man many consider to be the most vicious in Chicago gangster history.

by Allan May

When FBI agents and members of the Chicago Police Department’s Organized Crime Unit showed up to monitor the mourners at "Mad Sam" DeStefano’s funeral, they were disappointed, but not surprised. The "puny" turnout, which included a 10-car caravan to the cemetery, only amplified what law enforcement had known for years: "Mad Sam" was despised by everyone who knew him.

DeStefano was born in 1909. In what would prove to be a fitting start to his vicious criminal career, DeStefano, at age 18, was convicted of raping a teenage girl and sent to prison for three years.

In 1932, as a member of Chicago’s infamous "42 Gang," he was shot during an attempted burglary of a grocery store. By 1933 he was back in prison, this time for robbing a bank in New Lisbon, Wis. DeStefano was captured while climbing a tree to escape after the getaway car broke down and the robbers took off into the woods. He served 11 years before his release in 1944.

"Mad Sam" DeStefano

The story of a man many consider to be the most vicious in Chicago gangster history.

by Allan May

Charles "Chuckie" Crimaldi worked as a "juice collector" for Sam DeStefano during the 1950s and 1960s. He claims that Sam pioneered "organized" loansharking in Chicago, and, because of his success, he had the permission of Anthony Accardo and Sam Giancana to stay independent. Crimaldi claimed DeStefano "could make loans anyplace in the city irrespective of the jurisdiction allocated to the sharks who came later after Sam had greased the skids."

DeStefano’s independent status was confirmed by Roemer who wrote that Sam once told him that he was never a made guy because he could never submit to the discipline of the outfit. Crimaldi reported that one of Sam’s pastimes was to drive along lonely country roads and look for burial grounds for his future victims. "We could bury a dozen guys there and nobody would ever find a smell of ‘em." He would also go to pig farms and stare at the pigs for as long as an hour contemplating how he would feed his victims to the pigs so he could destroy the "evidence."

When DeStefano was upset his face pinched up and his eyes narrowed. His voice became gravelly and he spoke his words very slowly and punctuated his conversation with the filthiest profanity. In addition, DeStefano’s eyes bulged, his lips drew back to reveal an evil smile, and he would begin to drool. He was a cautious man, almost to the point of being eccentric. He once sent a gold watch, engraved with, "To Bob from Sam" as a gift to a politician who owed him several hundred thousand. He explained his reason for sending the watch this way: "That way, if we have to whack him, everybody’ll think we were friends; and I won’t draw no heat from the dead son-of-a-bitch."

Tommy Eboli
Tommy Eboli ran the Genovese crime family for nine years, and some thought he nearly ran it into the ground.  But it was a drug deal gone sour that ended his reign as one of the most powerful gangsters in the nation.

by Allan May

When Vito Genovese went to prison in 1960 for narcotics violations, he had every intention of returning to run his crime family.

In Genovese’s absence, the triumverate of Thomas Eboli, Gerardo Catena, and Mike Miranda were selected to hold down the fort. Thomas "Tommy Ryan" Eboli was the youngest of the trio and was looked upon as the first among equals of the group. When Genovese died in prison in 1969, Eboli was elevated to the position of boss.

Eboli was born in Italy in 1911. Little is known about his early years. His arrest record, dating back to 1933, included a half-dozen arrests for gambling and disorderly conduct. Despite his long involvement with organized crime his only prison time was a 60-day sentence for assaulting a boxing referee. Eboli had been involved in the fight game during the 1940s and managed several boxers. In 1952, while managing boxer Rocky Castellani, Eboli became enraged over referee Ray Miller’s decision in a bout against Ernie Durando in Madison Square Garden. Eboli jumped into the ring and attacked Miller. Afterward he was banned from further participation in boxing.

Jack Zuta

The murder of Jake Lingle, a reporter for the Chicago Tribune, caused a firestorm of publicity and fatal problems for Zuta, so unlovely a hoodlum that his fellow Chicago gangsters despised him.

by Allan May

"We only kill each other," Bugsy Siegel said to a contractor who was worried about getting on Bugsy’s bad side in Las Vegas.

Siegel’s statement held true most of the time. When it didn’t, it created sensational newspaper headlines and outraged citizens. One sensational digression from this rule was the killing of Alfred "Jake" Lingle, a Chicago Tribune reporter, on the afternoon of June 9, 1930, in a crowded pedestrian underpass.

The Lingle case involved North Side mobster Jack Zuta, a hoodlum so sleazy that even his fellow gangsters could barely stomach him.

James Eppolito

Few writers get to tell about mob hits made on members of their own family. One writer who had the opportunity was Detective Louie Eppolito of the New York City Police Department. On the evening of October 1, 1979, the day Pope John Paul II visited the Big Apple, James Eppolito and his son were killed in Coney Island by members of the Gambino Crime Family.

by Allan May

Organized crime murders are often treated like sports statistics. Mark McGwire hit two home runs last night. Karl Malone dropped in 30 points. Terrell Davis scored three touchdowns. Two Gambino Crime Family members shot dead. Sometimes that’s all the information you get. Maybe it’s all you want.

Few writers get to tell about mob hits made on members of their own family. One writer who had the opportunity was Detective Louie Eppolito of the New York City Police Department. On the evening of October 1, 1979, the day Pope John Paul II visited the Big Apple, James Eppolito and his son were killed in Coney Island by members of the Gambino Crime Family.

Vincent "The Schemer" Drucci

Vincent "The Schemer" Drucci had the shortest tenure of any of Chicago’s North Side gang leaders. An Italian, he headed a gang that was dominated by Irish, German and Polish criminals. A mob rarity, he was given a 21-gun salute at his funeral. But most notably, he may have been the only mob boss ever to be killed by a law enforcement officer.

by Allan May

Vincent "The Schemer" Drucci had the shortest tenure of any of Chicago’s North Side gang leaders. An Italian, he headed a gang that was dominated by Irish, German and Polish criminals. A mob rarity, he was given a 21-gun salute at his funeral. But most notably, he may have been the only mob boss ever to be killed by a law enforcement officer.

The leaders of the North Side Gang during the 1920s were Dion O’Bannion, Earl "Hymie" Weiss, Drucci, and George "Bugs" Moran. Of the four, Drucci was said to be the least known and least influential. The "Schemer" got his nickname from his ability to come up with hare-brained, "hits, heists and kidnappings." Early in his criminal career he gained a reputation for breaking into public pay phones. Laurence Bergreen, in his book, Capone: The Man and the Era, describes Drucci: "He had a streak of recklessness and daring, and he looked the part of a gangster – tough, dark, and menacing, his expression frozen in a tragic mask topped by wild unkempt hair (and) a face to haunt the dreams of his enemies."