Edgewater Beach Hotel was more than a place for union men to sleep in Chicago: it became a shared base where Frank Sheeran entered Jimmy Hoffa’s inner circle, observed the group’s private routines, and encountered figures connected to its wider network. The hotel’s suite offered an unusually intimate setting for relationships that later mattered to the account of Hoffa’s disappearance.

Union Lodging and First Encounters

The International Brotherhood of Teamsters kept a suite on the hotel’s eighteenth floor. It had two bedrooms, with two beds in each; Sheeran shared one room with Sam and Bill, while the other was theirs. The arrangement gave the men a common residence during their Chicago visits rather than a sequence of brief encounters in public offices.

Sheeran’s introduction to Joey Glimco came during his second night at the hotel. Bill explained that Glimco handled important problems for all Chicago locals, not just his own, and that Sheeran might be sent to him in the future. The hotel thus served as a point of entry into the union’s network of people and responsibilities.

The following night, Jimmy Hoffa arrived in Chicago. Sheeran met him at Joe Stein’s, across the street from the hotel, not in the suite itself. Hoffa listened as Sheeran spoke, asked about his daughters, and discussed the Teamsters’ expulsion from the AFL-CIO. Sheeran remembered him as personable and at ease despite the legal pressure around him. The exchange across the street began a relationship that the hotel’s later shared routines would make more familiar.

A Private Routine Around Hoffa

Sheeran later spent nights at Edgewater Beach Hotel, often rooming with Hoffa when Hoffa came in from Detroit. The men drank rum hidden in a hollowed watermelon so Hoffa would not know; when he noticed their enthusiasm, he remarked, “Boy, you men sure like your watermelon.” On another night Sheeran had left a gallon of wine cooling in the window. Hoffa came in while Sheeran was asleep, woke him, and asked, “What’s that in the window?” Sheeran answered, “I think it’s the moon, Jimmy.” Sam and Bill later said that Sheeran got away with more around Hoffa than anyone else.

The suite also reflected Hoffa’s habits as a father and a man who imposed a firm daily schedule. He was the first one up each morning, and breakfast was at seven sharp; those who were not ready got no breakfast. His son, young Jimmy, visited the hotel. Hoffa took pride in the fact that his son planned to attend law school, which he did, later becoming Teamsters president. These domestic details place the hotel’s political and labor connections beside the ordinary rhythms of family and shared lodging.

A Meeting Place in a Wider Network

Sam Giancana came to the hotel and visited Hoffa’s suite. At first, Sheeran said, he would greet Giancana when he arrived but leave rather than stay for the business. Later, after Hoffa had come to know Sheeran’s work, Sheeran remained in the room when matters were being discussed. The change marks a shift in his access: he was no longer merely a visitor to the circle but someone trusted to be present during its dealings.

Sheeran also recalled meeting Jack Ruby at the hotel on several occasions when Ruby accompanied Giancana. He said Hoffa’s son met Ruby there too, and described Ruby’s associations with both Giancana and Red Dorfman. Sheeran’s account includes a group meal and Ruby’s bringing a blonde woman from Dallas for Giancana. A later postscript to Dan E. Moldea’s book recounts that, in a 1978 recorded conversation, Hoffa’s son confirmed his father’s relationship with Ruby. The hotel recollection therefore contributes to the book’s depiction of Hoffa’s connections, rather than serving only as a memory of Sheeran’s lodging.

Retrospective Significance

The hotel scenes acquire added weight from the book’s account of the events that followed Hoffa’s disappearance. The FBI’s early list of seven suspects included Sheeran, while the investigation expanded to nine when Tony Giacalone and Chuckie O’Brien were added. The narrative does not identify the hotel as the site of the disappearance or of the later reported meeting among senior mob figures. Its importance is instead relational: it shows Sheeran sharing quarters with Hoffa, gaining access to meetings, and encountering people whose names recur in the wider account of the case.

That contrast gives Edgewater Beach Hotel its particular significance in the narrative. The suite’s beds, breakfast hour, watermelon, and wine make closeness concrete; the same rooms also place Sheeran within a network whose business extended beyond the hotel. What begins as union lodging becomes a record of access and familiarity, the everyday setting through which the book establishes how near Sheeran stood to Hoffa and to the people around him.