Sam Giancana

Sam Giancana is presented as a powerful Chicago crime boss whose reach extended from the Teamsters pension fund to presidential politics, Cuba, and the Mafia’s dealings with the CIA. In Frank Sheeran’s account, Giancana is not a distant name in the criminal underworld but a recurring presence in James R. Hoffa’s inner circle: a visitor to Hoffa’s hotel suite, an associate of Jack Ruby, and a participant in conversations about elections and Cuba. His public notoriety and the violence attributed to him sit alongside a final, abrupt absence: he was killed days before he was scheduled to testify before the Church Committee.

Place in Hoffa’s circle

At first, Sheeran says, he stayed away when Giancana came to the Edgewater to see Hoffa, though he would greet him at the suite. As Hoffa came to know Sheeran’s work, Sheeran remained in the room during business. Giancana was already a conspicuous public figure, associated in the newspapers with celebrities, in contrast to the more private Russell Bufalino. The suite thus becomes a meeting point where union leadership and organized-crime figures encountered one another in ordinary, unceremonious circumstances.

Sheeran also places Jack Ruby in this network. Ruby sometimes accompanied Giancana to the Edgewater, and Sheeran recalls meeting him there more than once. He describes Ruby as connected not only to Giancana but also to Red Dorfman, and recounts a meal when Ruby brought a blonde woman from Dallas for Giancana. The book emphasizes the significance of this familiarity: James R. Hoffa’s son, James P. Hoffa, later confirmed to author Dan E. Moldea that he had described his father’s relationship with Ruby. Moldea wrote that he had secretly tape-recorded their 1978 telephone conversation. In this account, Ruby was known within Hoffa’s circle, not merely encountered by its members in passing.

Pension fund, elections, and Cuba

Giancana’s connections also intersect with the Teamsters pension fund. Sheeran describes Hoffa taking an off-the-books finder’s fee for approving loans brought by crime bosses, including Giancana. Customers paid ten percent of a loan, with that percentage divided between Hoffa and the boss who brought the business. The arrangement made the fund a source of capital and gave Hoffa a personal return, while the account stresses that he conducted business on his own terms. Giancana’s place in this system was therefore not simply social: he is named among the bosses who could bring borrowers into the lending network.

Politics became another subject of discussion between Giancana and Hoffa. According to Sheeran, Giancana said he would help John F. Kennedy against Richard Nixon and that he could arrange to fix Illinois. Hoffa tried to dissuade him, arguing that Kennedy’s brother, Bobby Kennedy, could not be controlled and recalling that the Kennedy family had failed to restrain him during the McClellan Committee hearings. Giancana, for his part, said Kennedy would help them remove Fidel Castro and recover their Cuban casinos. The two men disagreed over the political calculation: Hoffa distrusted the Kennedys and expected Nixon to prevail, while Giancana questioned what Republicans could do for them in Cuba.

The book connects this conversation to the 1960 election by stating that the Teamsters were the only union to support Nixon. It also reports that the History Channel attributed Kennedy’s victory in Illinois in part to Giancana’s alleged use of fraudulent ballots bearing the names of dead people. The distinction between the men’s conversation and the later claim matters: the episode presents Giancana as willing to discuss election fixing, but the account’s specific description of the ballots is a reported allegation rather than a scene Sheeran says he witnessed.

Cuba’s importance was personal as well as political. Sheeran recalls accompanying Bufalino there as Castro began confiscating casinos, racetracks, homes, and bank accounts. He remembers Bufalino as furious. Sheeran did not accompany Bufalino on a later trip, when Santo Trafficante was reportedly in Communist custody, but says he heard a rumor that Giancana sent Ruby to Cuba to distribute money in an effort to secure Trafficante’s release. Sheeran also places Giancana within a wider Florida network: at Joe Sonken’s Gold Coast Lounge, he says, Giancana’s associates met with Bufalino, Trafficante, and Carlos Marcello. The account identifies Trafficante’s lawyer, Frank Ragano, as someone lent to Hoffa to assist with trials connected to Bobby Kennedy and the Get Hoffa Squad.

Violence and federal scrutiny

Giancana’s reputation in the book is inseparable from the violence attributed to his organization. During the McClellan Committee hearings, Bobby Kennedy challenged him about his place in the criminal world and questioned whether he disposed of enemies by putting their bodies in trunks. Giancana laughed and invoked the Fifth Amendment; Kennedy responded with a taunt about the laughter. The exchange makes the hearings more than a contest of testimony: it stages a public confrontation between a prosecutor determined to expose organized crime and a witness who would not answer directly.

The book pairs that defiance with accounts of brutal killings said to have been ordered by Giancana. In 1958, after suspecting Gus Greenbaum of stealing, Giancana allegedly ordered Greenbaum and his innocent wife tortured and killed in their Phoenix home. The killing is described as a message to others in the organization to obey its rules. In 1961, William “Action” Jackson, a loan shark suspected of being a government informer, was taken to a meatpacking plant and tortured for two days before he died. The account says photographs of Jackson’s injuries were shown to men working across Giancana’s criminal empire. These episodes give the book’s references to his power a coercive dimension: violence was not only punishment but a means of enforcing discipline and broadcasting the consequences of suspected betrayal.

Sheeran’s later account of Hoffa’s suspicions adds a further, more serious allegation. In a volatile conversation, Hoffa claimed that Giancana, Trafficante, Marcello, and their associates had been involved in the assassination of John F. Kennedy, linking them to the same circle involved in the Bay of Pigs and the plot against Castro. This is presented as Hoffa’s claim, not independently established proof. Its narrative importance lies in how it enlarges the circle of secrets Hoffa believed he possessed and the danger he believed surrounded him.

Assassination before testimony

In 1975, the Church Committee held closed-door hearings on organized crime’s involvement in the Bay of Pigs invasion and the plot to kill Castro, including a suspected plan to use poison. The committee was chaired by Senator Frank Church. At the start of the hearings, the CIA acknowledged both Mafia assistance in the Bay of Pigs and the existence of the CIA-Mafia plot, known as Operation Mongoose. Sheeran’s account situates Giancana within this larger inquiry: a contemporary report in Time magazine identified him and Bufalino as crime bosses behind the mob’s connections to the CIA, the invasion, and the assassination scheme.

Giancana was assassinated on June 19, 1975, five days before his scheduled testimony to the committee. He therefore never testified. His lieutenant Johnny Roselli did testify under oath behind closed doors; months later, Roselli was also assassinated, and his body was found stuffed in an oil drum. The sequence leaves Giancana at the center of a story the hearings could investigate but he could not narrate for himself. In the book, his importance rests on the breadth of the relationships attributed to him—and on the unresolved questions that his death, just before testimony, left behind.