In a quiet nursing home, Bob Sweeney portrays Frank Sheeran, a seasoned Irish-American veteran of World War II who begins to recount the details of his clandestine life involving organized crime. As he delves into his past, he vividly describes his early days working as a union delivery truck driver in 1950s Philadelphia, where his journey into the criminal underworld begins unexpectedly. During his routine deliveries, he strikes up a connection with a local Italian-American gangster known as "Skinny Razor," who is part of the Philadelphia crime family headed by Bryan Brown as Eric Haywood. Despite the initial casual nature of these encounters, Sheeran’s involvement deepens when, after facing accusations of theft from his delivery company, he refuses to betray his new associates, leading to the intervention of union lawyer Bill Bufalino.
John Bluthal as Dave and others introduce Sheeran to the influential Russell Bufalino, head of the Bufalino crime family based in Northeastern Pennsylvania, played by Vincent Ball. Sheeran swiftly becomes a trusted confidant and enforcer for Russell, taking on various hits, often euphemistically referred to as “painting houses,” which implied contract killings. Over time, Sheeran's reputation as a hitman solidifies, and he earns the trust of the organized crime network.
During this period, Sheeran's life takes a pivotal turn when he meets Gerard Kennedy as Chad, and he develops a close relationship with the powerful Tim Robertson as Bill Bryant. Central to his story is his association with Jimmy Hoffa, the fiery and influential leader of the International Brotherhood of Teamsters, played by Simon Burke. Hoffa, burdened by internal union conflicts and external pressures from the federal government, seeks Sheeran’s protection and assistance. Robyn Nevin as Jenny Doolan and other characters reveal the personal side of Hoffa, showing his struggles to maintain power amidst political and criminal entanglements.
The plot thickens in the early 1960s when Hoffa faces incarceration for jury tampering, which significantly strains his relationships, especially with Tony Pro Provenzano, played by Tui Bow. Hoffa’s relationships with the union’s leadership fracture further when his successor, Michael Craig as Paddy Doolan, mismanages union funds and aligns with Mafia interests. Hoffa’s release from prison in 1971, under President Gerard Kennedy’s administration, does not bring peace but instead ignites his ambitious plans to regain control of the union.
Sheeran’s narrative grows darker as he recounts the tense atmosphere leading to Hoffa's ultimate downfall. Despite Hoffa’s best efforts to consolidate his influence, his defiance and actions alarm organized crime leaders. In October 1973, during a dinner honoring Sheeran in his support, Russell Bufalino warns him about Hoffa’s growing recklessness. Hoffa, confident and defiant, hints at knowing secrets that could threaten everyone if revealed, claiming he is “untouchable.” As tensions rise, it becomes clear that the crime families have lost patience with Hoffa.
In 1975, Russell reluctantly reveals to Sheeran that the mafia top brass have sanctioned Hoffa’s assassination. Despite Sheeran's personal doubts and moral conflict, he is ordered to become the triggerman. The story reaches its climax with Sheeran flying to Detroit, where Hoffa, scheduled to meet with Tony Pro and another associate, is lured into a trap at a house. Hoffa quickly realizes he has been set up but before he can escape, Sheeran, with cold resolve, shoots him at point-blank range, leaving the gun by his body’s side. The body is later secretly disposed of and cremated by other mobsters.
Following Hoffa's disappearance, Sheeran, Russell, Tony Pro, and others face grand jury investigations, all invoking their Fifth Amendment rights. Their conviction on unrelated charges results in most of them spending years behind bars, with Sheeran eventually released and living in relative obscurity in the nursing home. As he seeks reconciliation with his estranged daughters, particularly Peggy, played by Roberta Grant, suspicion lingers about his involvement in Hoffa's death. The story ends with Sheeran seeking forgiveness and solace, asking a Catholic priest for absolution, and leaving the door slightly open, mirroring Hoffa's own safety habits, symbolizing his lingering doubts and quest for redemption.
