Giancana was born Salvatore Giangana, in The Patch on Chicago's West Side, to Italian Sicilian immigrants from Partanna, in the province of Trapani. His father, Antonino (later simplified to Antonio) Giangana, owned a pushcart and later briefly owned an Italian ice shop, which was later firebombed by gangland rivals of his son.
Sam Giancana joined the 42 Gang, a juvenile street crew answering to political boss Joseph Esposito. Giancana soon developed a reputation for being an excellent getaway driver, a high earner, and a vicious killer. After Esposito's murder, in which Giancana was allegedly involved, the 42 Gang was transformed into a de facto extension of the Chicago Outfit. The Outfit was initially wary of the 42ers, thinking they were too wild. However, Giancana's leadership qualities, the fact that he was an excellent "wheel man" with a get-away car, and his knack for making money on the street gained him the notice of Cosa Nostra higher-ups like Frank "The Enforcer" Nitti, Paul "The Waiter" Ricca, and Tony "Joe Batters" Accardo. He was arrested for the first time in 1925, for auto theft. He soon graduated to "triggerman," and by the age of 20 had been the prime subject in three murder investigations, but was never tried. In the late 1930s, Giancana became the first 42er to join the Outfit. From the early 1940s through the 1950s, he controlled most of the illegal gambling, illegal liquor distribution, and numerous other political rackets in Louisiana through longtime friend H.A. (Hol) Killian. Killian controlled the mass majority of the liquor license issuance to those who sought one through his connections with longtime business associate Carlos Marcello from New Orleans. The trio's combined political influence reached all the way to the governor's mansion and to the White House. Killian was such close friends with Giancana that the latter considered Killian's three sons (David, Mike, and Ned) as his own.
Giancana married Angelina DeTolve, the daughter of immigrants from the Italian region of Basilicata, on September 23, 1933. They had three daughters, Antoinette, Bonnie and Francine. His wife died in 1954, leaving him to raise his daughters. Giancana never remarried and was known as a good family man, despite frequent infidelities, and held his late wife in high regard and respect. All of the Giancana daughters have married at least once. As of 1984, at least one daughter, Antoinette, had taken the "Giancana" name again.
In 1945, after serving a sentence at the Federal Correctional Complex, Terre Haute, Indiana (during which time he told his children he was away "at college"), Giancana made a name for himself by convincing Accardo, then the Outfit's underboss, to stage a take-over of Chicago's African-American "policy" (lottery) pay-out system for The Outfit. Giancana's crew is believed to have been responsible for convincing Eddie Jones to leave his racket and leave the country. Giancana's crew was also responsible for the murder on August 4, 1952 of African American gambling boss Theodore Roe. Both Jones and Roe were leading South Side "Policy Kings". However, Roe had refused to surrender control of his operation as the Outfit had demanded; on June 19, 1951, Roe fatally shot Lennard "Fat Lennie" Caifano, a made man in Giancana's crew. Over an FBI wiretap during the early 1970s, Giancana said of Roe, "I'll say this. Nigger or no nigger, that bastard went out like a man. He had balls. It was a fuckin' shame to kill him."
However, the South Side "policy"-game takeover by the Outfit was not complete until another Outfit member, Jackie "the Lackey" Cerone, scared "Big Jim" Martin to Mexico with two bullets to the head that did not kill him. When the lottery money started rolling in for The Outfit after this gambling war, the amount that this game had produced for The Outfit was in the millions of dollars a year and brought Giancana further notice. It is believed to have been a major factor in his being "anointed" as the Outfit's new boss when Accardo stepped aside from being the front boss to becoming "consigliere," in 1957. However, it was generally understood that Accardo and Ricca still held the real power. Giancana was required to consult Accardo and Ricca on all important Outfit affairs. No major business transactions, and certainly no hits, took place without Accardo and Ricca's approval.
Giancana was present at the Mafia's 1957 Apalachin Meeting at the Upstate New York estate of Joseph Barbara. Later, Buffalo crime boss Stefano Magaddino and Giancana were overheard on a wire saying the meeting should have taken place in the Chicago area. Giancana claimed that the Chicago area was "the safest place in the world" for a major underworld meeting because he had several police chiefs on his payroll. If the syndicate ever wanted to hold a meeting in or around Chicago, Giancana said, they had nothing to fear because they had the area "locked up tight."
It is widely reputed and partially corroborated by the Church Committee Hearings, that during the Kennedy administration, the Central Intelligence Agency (CIA) recruited Giancana and other mobsters to assassinate Cuban dictator Fidel Castro. Giancana reportedly said that the CIA and the Cosa Nostra were "different sides of the same coin."
Judith Exner claimed to be the mistress of both Giancana and JFK and that she delivered communications between the two regarding Fidel Castro. However, Giancana's daughter, Antoinette, has stated her belief that her father was running a scam in order to pocket millions of dollars in CIA funding.
Documents released in 1997 revealed that some Mafiosi worked with CIA on assassination attempts against Cuban leader Fidel Castro. CIA documents released in 2007 confirmed that in the summer of 1960, CIA recruited ex-FBI agent Robert Maheu to approach the West Coast representative of the Chicago mob, Johnny Roselli. When Maheu contacted Roselli, Maheu hid the fact that he was sent by CIA, instead portraying himself an advocate for international corporations. He offered to pay $150,000 to have Castro killed, but Roselli declined any pay. Roselli introduced Maheu to two men he referred to as "Sam Gold", and "Joe." "Sam Gold" was Sam Giancana; "Joe" was Santo Trafficante, Jr., the Tampa/Florida /Miami Syndicate boss and one of the most powerful mobsters in pre-revolution Cuba. Glenn Kessler of The Washington Post explained: "After Fidel Castro led a revolution that toppled the government of Fulgencio Batista in 1959, CIA was desperate to eliminate Castro. So the agency sought out a partner equally worried about Castro—the Mafia, which had lucrative investments in Cuban casinos."
According to the recently declassified CIA "Family Jewels" documents, Giancana and Santo Trafficante, Jr. were contacted in September 1960, about the possibility of an assassination attempt by a go-between from CIA, Robert Maheu, after Maheu had contacted Johnny Roselli, a Mafia member in Las Vegas and Giancana's number-two man. Maheu had presented himself as a representative of numerous international business firms in Cuba that were being expropriated by Castro. He offered $150,000 for the "removal" of Castro through this operation (the documents suggest that neither Roselli, Giancana, nor Trafficante accepted any sort of payments for the job). According to the files, it was Giancana who suggested using poison pills that could be used to doctor Castro's food and drink. These pills were given by CIA to Giancana's nominee, Juan Orta, whom Giancana presented as being a corrupt official in the new Cuban government and who had access to Castro. After a six attempts to introduce the poison into Castro's food, Orta abruptly demanded to be let out of the mission, handing over the job to another, unnamed participant. Later, a second attempt was mounted through Giancana and Trafficante using Anthony Verona, the leader of the Cuban Exile Junta, who had, according to Trafficante, become "disaffected with the apparent ineffectual progress of the Junta". Verona requested $10,000 in expenses and $1,000 worth of communications equipment. However, it is unclear how far the second attempt went, as the entire program was canceled shortly thereafter due to the launching of the Bay of Pigs Invasion in April 1961.
At the same time, Giancana, according to the "Family Jewels", approached Maheu to wire the room of his then-mistress Phyllis McGuire, whom he suspected of having an affair with comedian Dan Rowan. Although documents suggest Maheu acquiesced, the device was not planted due to the arrest of the agent who had been given the task of planting the device. According to the documents, Robert Kennedy moved to block the prosecution of the agent and of Maheu, who was soon linked to the wire attempt, at CIA's request. Giancana and McGuire, who had a long lasting affair, were originally introduced by Frank Sinatra. During part of the affair, according to Sam's daughter Antoinette, McGuire had a concurrent affair with President Kennedy.
Giancana's behavior was too high-profile for Outfit tastes and attracted far too much federal scrutiny. He also refused to cut his underlings in on his lavish profits from offshore casinos in Iran and Central America. Both of these factors resulted in much bitterness among the Outfit's rank-and-file. Giancana was the subject of many hours of wiretaps. On one, he was heard to say, "We're whacking a lot of the wrong guys lately."
When Giancana was called before a grand jury in 1966, he was ordered to stay silent, which put him in prison for over a year. Meanwhile, Giancana was deposed as day-to-day boss by Ricca and Accardo, and replaced by Joseph "Joey Doves" Aiuppa.
After arriving in Mexico, Giancana managed to make money from various gambling operations, among them in Iran.
When Tony Accardo demanded that he give a share of the profits to The Outfit, Giancana refused, claiming that he did it all by himself and outside the Outfit's jurisdiction. In response, Accardo asked someone to "explain him the facts of life. And I mean life." Giancana, however remained adamant and refused to pay.
After his release from prison, Giancana relocated to Cuernavaca, Mexico in order to avoid further grand jury questioning. He was arrested by Mexican authorities on July 19, 1974 and deported to the United States. He arrived back in Chicago on July 21, 1974.
Giancana had another sitdown with the Outfit with no resolution. The Outfit requested he give a share of his money, and he refused.
After Giancana's return to the U.S., the police detailed officers to guard his house in Oak Park, Illinois. However, on the night of June 19, 1975, someone recalled the police detail. A gunman later entered Giancana's basement kitchen and shot him in the back of the head as he was frying sausage and peppers. After Giancana fell to the ground, the gunman turned him over and shot him six more times in the face and neck. Investigators suspected the murderer was a close friend whom Giancana had let into the house. One reason for this suspicion was that Giancana, due to his heart problems, could not eat spicy foods. Therefore, he might have been cooking for a friend. Giancana was killed shortly before he was scheduled to appear before the Church Committee investigating CIA and Cosa Nostra collusion in plots to assassinate President John F. Kennedy.
Hit man Nicholas Calabrese told the FBI in the 2000s that he knew that Tony Accardo was part of the killing, and Angelo LaPietra got rid of the gun. The gun used to kill Giancana was equipped with a suppresser that Frank Calabrese, Sr. and Ronnie Jarret had made.
Giancana was interred next to his wife, Angelina, in a family mausoleum at Mount Carmel Cemetery, in Hillside, Illinois.
Some commentators have alleged that CIA killed Giancana because of his troubled history with the agency. However, former CIA Director William Colby has been quoted as saying, "We had nothing to do with it."
Another theory is that Trafficante crime family boss, Santo Trafficante, Jr., ordered Giancana's murder due to mob fears that Giancana would testify about Cosa Nostra and CIA plots to kill Fidel Castro. Trafficante would have needed permission from Outfit bosses Tony Accardo and Joseph Aiuppa to kill Giancana. Johnny Roselli, whose body was found to have been shot, dissected, then stuffed in an oil drum floating off Miami, was also rumored to have been killed on Trafficante's orders.
Most investigators believe Aiuppa ordered the Giancana murder. Giancana was still refusing to share any of his offshore gambling profits with the Outfit. In addition, Giancana was reportedly scheming to become Outfit boss again.
Longtime associate Dominic "Butch" Blasi was with Giancana the night he was murdered and was questioned by police as a suspect. FBI experts and Giancana's daughter, Antoinette, do not consider him Giancana's killer.
In the movie Sugartime (1995), Dominic "Butch" Blasi, as portrayed by Elias Koteas, is shown murdering Giancana.
According to former Mafia associate Michael J. Corbitt, Aiuppa seized control of Giancana's casinos in the aftermath of the murder, strategically sharing them with his caporegimes.
Within days of Giancana's murder, Willow Springs police chief and Outfit associate Michael J. Corbitt discussed the murder with capo Salvatore Bastone. Bastone told him, "You know, Sam sure loved that little guy in Oak Park... Tony Spilotro. Yeah, he was fuckin' crazy about him. Sam put Tony on the fuckin' map, thought he was gonna be a big fuckin' man someday. Did you know that after Marshall Caifano got out of Vegas, it was Sam who wanted Tony Spilotro out there? Even lately, with all the problems with the skim and all, Sam always stood behind the guy. Tony was over to Sam's house all the time. He lived right by there. Did you know Tony even figured out a way where he could get in through the back of Sam's place without anybody seeing him? He'd go through other people's yards, go over fences, all sorts of shit."
Corbitt responded, "Sam wouldn't open the door for just any son of a bitch. I mean there's Butch, Chuckie English... He'd let them in alright, but shit, no way they'd ever do anything to hurt Sam. No way."
Bastone then said, "Yeah, Sam and Butch were real close. And the same thing with him and Chuckie. Besides, neither one of them had the balls to do somethin' like that. There's only one guy that had the balls to do Sam."
When Corbitt asked for the reason, Bastone quipped, "There's never just one reason for shit like what happened to Sam. There's a million of 'em. Let's just say that Sam should've remembered what happened to Bugsy Siegel."Giancana played a major role in the J. X. Williams film Peep Show (1965) and has a personal performance credit for this on the IMDb movie data-base.
The HBO made-for-TV film Sugartime (1995) depicts Giancana's relationship with singer Phyllis McGuire of the McGuire Sisters, with Giancana being played by John Turturro.
Peter Friedman played Giancana in the film Power and Beauty (2002).
Robert Miranda played Giancana in the TV film, The Rat Pack (1998).
Carmine Caridi played Giancana in the film Ruby (1992).
News footage of Giancana is featured in the film JFK (1991).
Giancana is portrayed under the name "Joseph Palmi" in the film, The Good Shepherd (2006), starring Matt Damon. Palmi may be a mix of the several other mobsters (Santo Trafficante, Jr., Carlos Marcello, etc.) involved with the operation. Matt Damon's character, Edward Wilson, is depicted in proposing Palmi (Joe Pesci) to assist in the assassination of Fidel Castro. Pesci also played Nicky Santoro in Casino, who was based on Tony Spilotro.
Giancana is a central figure in Max Allan Collins' novels Chicago Confidential and Road to Paradise.
Giancana plays a major role in James Ellroy's fiction, most notably American Tabloid and its sequels The Cold Six Thousand and Blood's a Rover.
Giancana is the subject of the biography Mafia Princess, written by his daughter Antoinette. This book was later adapted into the TV film Mafia Princess (1986), starring Tony Curtis as Giancana.
Giancana is a character in Robert Randisi's Rat Pack novels.
Giancana is a notable character in Norman Mailer's historical fiction "Harlot's Ghost".
The fictional character "Sam" in Steve Peters and Kay Stephens' novel The Outlaw Sandra Love (2013) is based on Giancana.
The fictional character Louie Russo from Mark Winegardner's novel The Godfather Returns, could be based on Sam Giancana.
The book "Double Cross: The Explosive, Inside Story of the Mobster Who Controlled America" tells the story of Sam Giancana's life. Written by his brother Chuck Giancana, and his godson and namesake Sam Giancana, the book includes stunning first-time revelations concerning the deaths of JFK, Marilyn Monroe, and RFK.
In the 2013 novel The Outlaw Sandra Love, the protagonist Sandra Love is said to have had a four-year relationship with a man named Sam the head of the Chicago Outfit in the early 1960s.
Influential mafioso-rapper Kool G Rap once stated that the "G" in his name stands for Giancana. Kool G Rap released an album in 2002 called The Giancana Story (2002).
Giancana may be mentioned in the Shyne song "Edge" on his second album Godfather Buried Alive. "Fuck comma rap's, Sam Giancana", although this is sometimes rendered as "... same G and canna".
Giancana is mentioned in the song "Dope money" by The Lox. "Bring Drama 'cause Giancana got Kennedy Killed". "Dope money" is the sixth track on The LOX second album, Ryde or Die Vol. 1.
Giancana features in the first episode of the documentary series Mafia's Greatest Hits, on the UK history TV channel Yesterday.
Rod Steiger portrayed Giancana in the TV miniseries Sinatra (1992).
Serge Houde portrays Giancana as a major nemesis of the Kennedy family in the television miniseries The Kennedys (2011).
The character Mob Man (uncredited) from The X-Files episode "Musings of a Cigarette Smoking Man" is likely based on Giancana who is present at a planning meeting on the assassination of JFK.
Giancana is portrayed by Emmett Skilton in the 8-part AMC television miniseries, "The Making of the Mob: Chicago" (2016).