Puerto Rico appears as more than a stop on Frank Sheeran’s itinerary: it is a battleground over who would represent dockside drivers, a setting for a provocative political gesture, and one destination in a chain of assignments issued by Jimmy Hoffa. The account ties local union disputes to the wider struggle over the Teamsters and the AFL-CIO, while leaving the specific acts Sheeran carried out on the island undisclosed.

Labor jurisdiction and conflict

Frank Chavez, a loyal supporter of Jimmy Hoffa in Puerto Rico, wanted Teamsters representation for drivers who hauled cargo away from ships. The Seafarers International Union, led by Paul Hall and affiliated with the AFL-CIO, also sought to represent those waterfront workers. The disagreement turned on the workers’ overlapping identities: they worked at the docks, but they were drivers. Hoffa and Hall already hated each other, and the dispute became part of a larger confrontation over the Teamsters’ standing and power.

The conflict is described as a bloody war in which both sides had their own hit squads. Puerto Rico therefore enters the narrative not as a remote backdrop to union politics but as a place where jurisdictional rivalry could take a violent form. The account links that local contest to Hall’s role in the AFL-CIO’s expulsion of the Teamsters and to Hoffa’s belief that Hall was working to bring him and the union down.

Chavez’s letter and its political setting

Chavez’s conduct also made him a volatile Hoffa ally. On the day John F. Kennedy was assassinated, Chavez sent Bobby Kennedy a letter on behalf of his Puerto Rican local. He said the local would place flowers on Lee Harvey Oswald’s grave and keep them fresh, framing the gesture as a response to what Bobby Kennedy had done to Jimmy Hoffa. The episode brings the island’s union politics into the national aftermath of the assassination, turning a local’s promised act of remembrance into a pointed act of retaliation.

The narrator condemns the gesture as cruelly timed: Bobby Kennedy had just lost his brother, and Oswald was a war hero who had saved his men in the PT-boat incident. The account holds these judgments together rather than excusing Chavez through his loyalty to Hoffa. Puerto Rico is thus associated both with the Teamsters’ struggle for representation and with the capacity of factional grievance to spill into a deeply charged public moment.

Sheeran’s assignment and the limits of the account

One night in Philadelphia, Hoffa called Sheeran and told him to fly to Puerto Rico the next morning, settle two matters there, then go to Chicago to settle another matter before meeting Hoffa at the Fairmont Hotel in San Francisco at 8:00 p.m. The itinerary compressed several cities and assignments into a single day, with Puerto Rico as the first stop.

Sheeran later described the euphemism behind such instructions: a superior would ask him to straighten a matter out, and people at the destination would already have arrangements in place. He said he took care of two matters in Puerto Rico, then one in Chicago, before flying on to San Francisco. The book does not specify what the Puerto Rico matters were, so their nature cannot be established from this account. That withheld detail is significant to the location’s narrative role: Puerto Rico is shown as a place where Hoffa’s authority could dispatch Sheeran, while the work itself remains obscured behind the language of routine business.