Killing of Lee Harvey Oswald

The Killing of Lee Harvey Oswald enters the book not as a narrated scene but as a question Frank Sheeran says crossed his mind after the assassination of John F. Kennedy. His recollection links the news from Dallas to an earlier matter at Monte’s, but he offers no evidence that the events were connected. The episode’s significance lies in the suspicion it preserves—and in the silence surrounding what could be asked about it.

The Event in Retrospect

Sheeran places his recollection in Wilmington, where the union hall was near the train station and still belonged to Local 107 in Philadelphia. He had gone there on union business and stopped at trucking terminals along the way. When he entered the hall, the radio was reporting that Kennedy had been shot. Sheeran says the news affected him, though Kennedy was not one of his favorite people; he also recalls having no personal grievance against him and remarks on Kennedy’s family.

Before Ruby killed Oswald, Sheeran says, the news made him wonder whether the killing had anything to do with “that matter at Monte’s.” He does not specify what that matter was in this recollection. The account therefore establishes that the possibility occurred to him, not that he knew of a connection or could demonstrate one.

Ruby and the Chicago Connections

Elsewhere, the book identifies Ruby as the man who killed Oswald while recounting Frank Sheeran’s claims about Red Dorfman and union influence. Sheeran says that Red had Jack Ruby with him as the other officer in a Chicago waste handlers’ union, and connects Red with Ruby’s boss, Sam “Momo” Giancana, as well as Joey Glimco and other Chicago figures. These are relationships as presented in Sheeran’s account; they provide a wider underworld context for Ruby’s name without establishing a motive for the killing of Oswald.

The two references do different work. The union story places Ruby within a network described by Sheeran, while the Wilmington recollection records his private speculation after Kennedy’s assassination. Neither passage supplies an account of the killing itself, the circumstances in which it occurred, or corroboration for a link to Monte’s.

Evidence and Limits

The recollection comes through the book’s extended interview process, rather than through an independent reconstruction of the Oswald killing. The author says that an initial interview with Sheeran in 1991 ended when Sheeran reconsidered the questioning; interviews resumed after Sheeran contacted him following a meeting with a monsignor and continued for four years. The author describes his own experience as a prosecutor and interviewer, and says he sought to preserve Sheeran’s rights so that the statements would not become a legally admissible confession.

Sheeran read and approved each chapter and later the complete manuscript. That process documents his approval of the book’s presentation, but it does not independently verify the speculation about Monte’s. In the passages concerning Oswald, the distinction matters: Ruby’s killing of Oswald is stated, Sheeran’s suspicion is recalled, and the possible connection remains unresolved.