Chicago Outfit boss Sam Giancana killed 50 years ago

Late in the evening of June 19, 1975,  Sam “Momo” Giancana was cooking in his basement apartment, presumably for a guest. Before the late-night meal could be served, Giancana was shot in the back of the head.

The murder of the former Chicago Outfit boss remains one of the most debated unsolved homicides in organized crime history. His tumultuous final years fuel several theories about his demise. Over the course of his long career filled with violence and political maneuvering, Giancana provided motives to rivals and allies alike.

From infamy to fame

Born Salvatore Giancana on June 15, 1908, in Chicago to Sicilian immigrants, Giancana was raised in the rough Italian neighborhood known as “The Patch.” Like many of his contemporaries, he was lured into the criminal world at a young age. His early connections with street gangs, such as the 42 Gang, laid the groundwork for a lifetime of criminal activity. Known for his fierce temper and sharp intellect, Giancana quickly built a reputation for brutality and loyalty, which helped him win the favor of established members of the Chicago Outfit — Chicago’s powerful and feared crime group.

Giancana’s true rise began under the guidance of then Outfit leader Tony Accardo. Throughout the 1940s and early ’50s, Giancana served as a ruthless and effective enforcer, managing gambling and loan-sharking operations for Accardo. His increasing influence and knack for generating revenue solidified his position in the Outfit’s upper echelons. When Paul “The Waiter” Ricca and Accardo chose to step back from daily operations in the mid-’50s, they chose Giancana to act as the front boss, effectively becoming the public face of the Chicago Mob. Behind the curtain, Accardo still held significant power, but Giancana had substantial control over the organization’s vast enterprises.

During his time as boss, Giancana broadened the Outfit’s influence into Las Vegas casinos, Latin America and Hollywood. He was especially known for building high-profile connections, most notably with the Kennedys, the CIA and celebrities. Giancana collaborated with U.S. intelligence agencies on schemes to assassinate Cuban leader Fidel Castro. His connections to Frank Sinatra and an affair with singer Phyllis McGuire further propelled him into the limelight.

Giancana had become a public figure — which never sits well with the Mob.

Giancana wound up facing government inquiries, including those of Mob-busting Attorney General Robert F. Kennedy. Giancana refused to talk and, in 1965, was jailed for contempt. Ricca and Accardo had oversight of the Outfit during Giancana’s reign, albeit from the shadows.  When Giancana was imprisoned, Accardo stepped back into the acting leadership role.

After Giancana’s release in 1966 he hastily fled to Mexico and established business endeavors south of Mexico City in Cuernavaca. He remained there until 1974 when, as declassified CIA and FBI documents show, Mexican officials detained Giancana on July 19, 1974, and moved to expel him. He returned to American soil two days later. Although still a powerful figure in the Chicago Mob, Giancana’s leadership days were over.

In 1974, journalist Seymour Hersh released a front-page story in the New York Times, alleging that the CIA had been monitoring anti-war activists for more than 10 years, breaching its charter. This revelation, along with the Watergate scandal and other wrongdoing by intelligence agencies, led lawmakers to demand an investigation.

On January 27, 1975, the Senate passed a resolution to form a committee to carry out a comprehensive investigation of the nation’s most secretive agencies and programs over the next year (later extended to 16 months). The Church Committee pinpointed programs for examination and started requesting documents from intelligence agencies. Giancana was one of the individuals summoned to appear before the committee.

That summer, Giancana went to Houston to visit friends but became ill. He checked into a hospital and underwent gall bladder surgery. According to Dominic “Butch” Blasi (who had been an FBI asset for some time), Giancana had a limited list of who could visit him while recuperating in the hospital, which included Blasi and Carolyn Morris, Giancana’s girlfriend at the time.

After recovering, Giancana returned to his home in Oak Park, a Chicago suburb, and threw a little party on the evening of June 19, 1975.

All the guests departed sometime around 11 p.m. Another person or persons arrived at Giancana’s home and entered through a back entrance leading to Giancana’s basement apartment. Giancana, likely familiar with and/or expecting the guest, casually began cooking up a small meal.

The longstanding version of Giancana’s last moments is a scenario of Giancana hovering over a pan cooking up sausage and peppers, presumably a dish intended for his guest. His back to the mystery guest, Giancana received a shot or two to the back of the head from a .22 pistol equipped with a silencer. The shooter then put more shots into the victim’s face and neck.

There is no shortage of theories floating around about who took out Giancana and why. One theory has fellow Chicago mobster Tony Spilotro killing him as a personal vendetta. Others claim it was Blasi, acting on behalf of the Outfit over money or power struggles. Other theories propose the CIA did it as a cover-up for either the Castro assassination plot or the Mob’s alleged role in the JFK assassination.

Blasi was the last person to see Giancana alive, a fact he never denied. Blasi was never charged despite being one of the most likely suspects. The theories of government involvement may technically be possible, but unlikely. In a piece for MafiaHistory.us, Edmond Valin gave a possible origin for this theory, writing that Blasi once told FBI agent Bill Roemer, “Giancana was killed by ‘forces outside of organized crime.’”

Valin continues, “This seems to be a suggestion that Giancana’s murder was tied up somehow in his role in the Central Intelligence Agency plot to kill Cuban leader Fidel Castro. A more likely reason was that Outfit leaders believed Giancana was going to talk about his criminal history in Senate committee hearings set to begin a few days later.”

Recent reports suggest the looming appearance before the Church Committee may have indeed been the final nail in the proverbial coffin.

NBC5 Chicago aired a two-part series in May with investigative reporter Chuck Goudie revisiting the Giancana case. Goudie offered a bold revelation of the identity of the actual culprit that fateful night in 1975. According to his research, the hit on Giancana wasn’t just ordered by Accardo, it was carried out by the boss personally.

In the televised version and subsequent written articles, Goudie’s team of reporters revealed findings in previously unseen documents, spoke to four investigators involved in the case and interviewed former Mob associate Frank Calabrese Jr. All four investigators firmly believed Accardo pulled the trigger, though it could not be proven. The .22 used in the murder (which had been purchased in Florida) was recovered in a location between Giancana’s home and Accardo’s. What’s more, the FBI had Accardo’s home under surveillance that evening and their report noted Accardo’s car leaving before 11 p.m. and returning shortly thereafter. Interestingly, Giancana’s home was being watched by cops, too, but those officers called it a night and left the area shortly after the original partygoers retired.

Referring to the Church Commission dilemma, Calabrese Jr. told Goudie, “Sam was the one that could really get Tony in a lot of trouble.”

Some have described Accardo as the epitome of a tough street guy, old school, who believed in taking care of business himself, if necessary, even if you’re the boss. His street reputation started with his days as a baseball bat-wielding muscle man for Al Capone, allegedly giving him his nickname, “Joe Batters.” It was characteristic of him to personally resolve a loose end.

And, besides Dominic Blasi, there are very few people Giancana would have ever welcomed into his basement unless he trusted them completely — or had no choice in the case of the boss.

Incidentally, the Goudie investigation also mentions Giancana’s last meal being sausage, escarole and beans, with no mention of peppers.

Christian Cipollini is an organized crime historian and the award-winning author and creator of the comic book series LUCKY, based on the true story of Charles “Lucky” Luciano.