Chicago is more than a setting in the book: it is a working hub where Frank Sheeran moves from peripheral union associate to trusted participant in Jimmy Hoffa’s circle, and where Teamsters business, organized-crime influence, and personal loyalty repeatedly converge. The city’s hotels and bars provide meeting places; its freight companies become sites of pressure; and a federal trial there turns the union’s financial dealings into a documentary case.

A city of meetings and networks

Sheeran’s first sustained work in Chicago begins after Bill and Sam recommend him to Hoffa. The three fly to the city and stay at the Edgewater Beach Hotel, in a union-kept suite on the eighteenth floor. Bill and Sam share one bedroom, while Sheeran sleeps in the other. There he is introduced to Joey Glimco, whom Bill describes as the person who handles important problems for Chicago locals beyond his own. The introduction establishes Chicago as a place where a local dispute can be routed through a broader network of union operatives.

Hoffa arrives the following night, and Sheeran meets him at Joe Stein’s, across from the hotel. Hoffa is at ease despite the pressure surrounding him, asks about Sheeran’s daughters, and explains his view of why the Teamsters had been expelled from the AFL-CIO: its leaders, he says, feared crossing Robert F. Kennedy and attracting the kind of investigation Hoffa had endured. The encounter gives Sheeran a direct view of Hoffa’s political grievance and personal manner, while the location places that conversation within the same Chicago circuit as union work and organized-crime contacts.

Chicago’s hotel rooms also become informal social spaces. Sheeran says he often stayed at the Edgewater, sometimes sharing with Hoffa when he came from Detroit. Bill and Sam secretly drank rum poured into a hollowed watermelon so Hoffa would not realize they were drinking. On another night, Sheeran hid a gallon of wine in the window; when Hoffa asked what it was, Sheeran answered that he thought it was the moon. The small episode adds an intimate, joking register to a setting otherwise associated with business and danger.

Labor pressure on the freight routes

Glimco sends Sheeran to Cicero to address a freight hauler that is resisting the union and has refused to rehire a fired shop steward. The assignment is framed as a problem that reflects on Glimco’s standing with his men. After Sheeran gets lost and enters a bar, about twenty rough-looking men surround him, each armed; Glimco eventually comes to collect him and take him to the correct meeting place.

Sheeran rejects the idea that anyone needs to be killed. Instead, he asks for a case of Coca-Cola in old-fashioned bottles and one of Glimco’s men. From a bridge near the freight company, the two drop bottles onto trucks as they pass beneath. The crashes frighten the drivers into refusing to take the trucks out of the yard. The company rehiring the shop steward ends the immediate dispute, though it does not pay him the back wages he is owed. The episode shows labor enforcement operating through intimidation and disruption, while Sheeran’s improvised method stops short of the killing he says was unnecessary.

The story places Chicago’s union activity within a wider criminal network rather than treating it as a sealed local world. Sam Giancana visits the Edgewater, where Sheeran initially greets him but does not remain for the business. Later, after Hoffa has come to know Sheeran’s work, Sheeran stays in the room when matters are discussed. Giancana sometimes brings Jack Ruby, whom Sheeran also encounters in the company of Red Dorfman. These contacts make the hotel a point of overlap among union figures and people connected to Chicago’s criminal circles.

Giancana, Hoffa, and the threat of exposure

The narrative returns to Chicago when Sheeran invokes the killing of Giancana during a telephone conversation with Hoffa. Sheeran describes Giancana as a good friend of Hoffa’s and says he had carried verbal messages between the two men. He recalls the public attention surrounding Giancana and the reporting that linked Giancana and Russell Bufalino to CIA activity around the Bay of Pigs invasion and a plot against Fidel Castro. According to Sheeran, Giancana was killed in his kitchen shortly before he was due to testify to the United States Senate about the CIA’s use of mob figures in the Castro operation.

In the call, Hoffa’s fear is not abstract. He warns that he keeps records and that, if anything unnatural happens to him, those records will come out. Sheeran counters by pointing to the Chicago killing as evidence that powerful people are not necessarily untouchable. The city therefore functions not only as the place associated with Giancana and the networks around him, but also as the reference point through which the book makes Hoffa’s vulnerability legible: records, political exposure, and lethal retaliation sit in the same conversation.

The pension-fund case

Chicago later becomes the venue for a federal prosecution over the Central States Pension Fund. On the same afternoon that Raymond Cohen was convicted of embezzling union funds, a grand jury in Chicago indicted Hoffa for allegedly misusing the fund for personal profit. The central allegation concerned a $400,000, interest-free pledge of union funds to secure a personal loan connected to the Sun Valley land development in Florida; prosecutors also alleged that Hoffa secretly held a 22 percent interest in the venture’s profits. Hoffa denied having that concealed interest.

The trial of Hoffa and seven codefendants began in Chicago on April 27, 1964, five weeks after Hoffa received an eight-year sentence in Chattanooga. As in that earlier case, the prospective jurors’ identities were withheld from both sides until jury selection began. Jury selection itself proceeded without incident, but the government then presented thirteen weeks of live testimony and more than 15,000 documents. The scale of the record made Chicago the setting for a prolonged, formal examination of union finance rather than a brief courtroom episode.

The case centered on Sun Valley Village, a Florida housing development intended for Teamsters who invested in lots for retirement or vacation homes. Hoffa was among those who purchased a lot, but the developer never completed the project and later died. The development went bankrupt, leaving the lots worthless. Chicago thus gathers two contrasting forms of power in the book: the local, personal networks visible in hotel rooms and freight disputes, and the federal scrutiny that converts pension-fund transactions into testimony, documents, and criminal charges.