Harold Gibbons

Harold Gibbons is a senior Teamsters official whose career in the book is marked by a contrast between union loyalty and political independence. He appears as a respected organizer and potential successor within the union, but also as a man willing to take positions that angered James R. Hoffa and drew hostile attention from the Nixon White House. His importance emerges through recurring decisions rather than through a sustained account of his private life: he led in St. Louis, honored a slain president, and later stood alone against his union’s endorsement of Richard Nixon.

A St. Louis union leader

Gibbons headed the Joint Council in St. Louis, where Bill Isabel was listed both as an organizer for a local and as an organizer for the council. Isabel, himself a seasoned union organizer, thought Gibbons was the person Hoffa should have put in charge when he went to prison in 1967, instead of Frank Fitzsimmons. That recommendation places Gibbons within the union’s senior leadership and makes him a credible alternative in the succession that followed Hoffa’s incarceration. The book does not say that Hoffa seriously considered or offered him the position; the proposal is Isabel’s judgment, recalled by Frank Sheeran.

Sheeran’s assessment of Gibbons is unusually emphatic. He calls him one of the finest and most dedicated union men, a description that distinguishes Gibbons from the figures in the narrative whose union authority is entangled with personal power or alleged criminal interests. This praise is still part of Sheeran’s retrospective account, not an independent evaluation. But it helps explain why Sheeran advised Hoffa to put Gibbons in charge of day-to-day operations rather than Fitzsimmons: in Sheeran’s view, Gibbons possessed the commitment and standing the job demanded.

The flag and Hoffa’s anger

After John F. Kennedy was assassinated, flags in Washington were lowered and government workers were sent home. Gibbons, then an International Vice President, lowered the flag at Teamsters headquarters and closed the building. Hoffa reacted furiously. Sheeran later told Hoffa that Gibbons had followed what other buildings were doing; he could not persuade Hoffa to accept that explanation. Hoffa never forgave Gibbons for the gesture.

The dispute mattered beyond the flag itself. On the day of the assassination, Gibbons’s response aligned the union headquarters with a public act of mourning, while Hoffa’s anger made the gesture a lasting test of personal loyalty. When Sheeran later urged Hoffa to appoint Gibbons to manage the union during his imprisonment, Hoffa rejected the suggestion with the terse response, “Fuck him.” The episode reveals the limits of Sheeran’s influence: he could recommend a trusted official, but could not overcome Hoffa’s resentment.

A trusted source in the Chicago negotiations

In January, Sheeran was with Hoffa in Chicago for the final signing of the first Master Freight Agreement. The agreement set national minimum terms while allowing local unions to negotiate supplements and better conditions; it did not eliminate local differences or prevent cheating. Sheeran describes the signing as an important moment for labor, while noting that the local unions still had to approve it and that leadership determined whether workers received the terms available to them.

Sheeran later heard from Gibbons that, after the events in Chicago, Hoffa took care to sign everything as “James R. Hoffa.” The account does not explain the particular document or the reason for the change in signing practice. Its significance lies in the small, reported detail: Gibbons remained a source of information about Hoffa’s conduct, and Sheeran’s recollection of Hoffa’s later caution came through him. Gibbons is thus present not only as a rival candidate for authority but also as a trusted point of contact in the union’s internal story.

The lone vote against Nixon

On July 17, 1972, the Teamsters executive board formally endorsed Richard Nixon for reelection by a vote of 19 to 1. Gibbons cast the sole dissenting vote. The book notes the pointed contrast with the earlier flag dispute: he was the same vice president whose decision to honor John F. Kennedy had enraged Hoffa. It also records a connection between the administration and the union leadership: Patricia Fitzsimmons, Frank Fitzsimmons’s wife, had been appointed by Nixon to the Arts Committee of the Kennedy Center for the Performing Arts.

The dissent was followed by evidence of political pressure directed at Gibbons. John Dean testified that Charles Colson asked him to initiate an IRS investigation into Gibbons’s finances. A memorandum from Colson to Dean requested the audit and called Gibbons an “all-out enemy.” Hoffa later testified in a deposition, “I blame one man [for the restriction on my pardon]…Charles Colson.” Colson invoked the Fifth Amendment when questioned about the matter during the Watergate hearings, though he acknowledged discussing Hoffa’s pardon with Fitzsimmons before it was granted. The account presents these statements and the memo as evidence surrounding the pardon restriction; it does not establish that Gibbons’s dissent alone caused the proposed audit or the restriction.

A visible dissenter in the union’s inner circle

Gibbons also appears at the testimonial dinner held for Hoffa’s sixtieth birthday in February 1973 at the Latin Casino in Cherry Hill, New Jersey. Fitzsimmons did not want people to attend, but Gibbons was the only executive-board member who showed up. Sheeran was there, seated prominently, and Hoffa posed with him for several photographs, including a handshake photograph Sheeran said he treasured. The scene places Gibbons among the few senior officials who publicly joined Hoffa’s supporters despite pressure from the man then leading the union.

Taken together, these episodes portray Gibbons through choices that acquired significance because of the people and institutions around him. He was recommended as a capable successor, rejected by Hoffa after an old grievance, and later the only board member to oppose the Nixon endorsement. The book offers no account of what Gibbons privately thought about these conflicts. Instead, it makes his position legible through the recorded actions: a lowered flag, a vote of one against nineteen, and an appearance at a dinner that the sitting union leadership would rather its members had avoided.