The story unfolds in the early 2000s within the confines of a retirement home, where Frank Sheeran (Robert De Niro) sits in solitude, contemplating the journey of his life that has brought him to this moment. His reflections delve into his past, beginning with his involvement as a "house painter," a euphemism for his role as a hit-man.
In the 1950s, Frank, a proud World War II veteran, resides in Philadelphia, Pennsylvania, earning a living as a truck driver for a meat-packing company. He shares his life with his wife, Mary (Aleksa Palladino), and their daughter, Peggy (portrayed by Lucy Gallina). His fate intertwines with that of Russell Bufalino (Joe Pesci), a local mobster who advises him on fixing his truck. The conversation steers away from personal introductions but sets a future connection in motion.
As Frank delves deeper into the underworld, he forges connections with the notorious gangster Felix "Skinny Razor" DiTullio (Bobby Cannavale). A turning point occurs when Frank is accused of theft by his employers after a delivery goes wrong. Seeking legal assistance, he turns to Bill Bufalino (Ray Romano), who advises him to protect the names of his associates. This leads to a formal introduction to Russell, marking Frank’s entry into the world of organized crime.
Things take a dramatic turn when Frank is approached by a gangster known as Whispers (Paul Herman), who tasks him with eliminating Russell and Angelo Bruno (Harvey Keitel). However, Frank chooses loyalty and informs them instead, showing his complex moral compass. One disturbing incident involving Peggy prompts Frank to confront a store owner violently, leaving his daughter terrified of him—a foreshadowing of their strained relationship.
Russell introduces Frank into the fold of crime, where he becomes an adept hit-man, intertwining his life with various gangsters, each meeting their grim fate as noted throughout the film. Frank’s personal life illustrates his departure from Mary as he embarks on a relationship with Irene (Stephanie Kurtzuba), later growing his family with two more daughters. The narrative weaves in Jimmy Hoffa (Al Pacino), the powerful leader of the International Brotherhood of Teamsters, who seeks Frank's expertise.
In a compelling moment, Frank learns of tensions between Hoffa and Teamsters Vice President Anthony "Tony Pro" Provenzano (Stephen Graham), hinting at the brewing conflicts ahead. Frank begins working alongside Hoffa, becoming a protector and confidant, while Peggy grows particularly fond of him, illustrating the blurred lines between familial ties and criminal allegiance.
As the 1960s unfold, tensions rise within the Teamsters, especially with the election of JFK, which troubles Hoffa. An ill-timed statement leads to Hoffa's arrest and subsequent fallout from his decisions while imprisoned. The landscape becomes perilous as violence escalates, notably orchestrated by the impulsive mobster Crazy Joe Gallo (Sebastian Maniscalco), requiring Frank’s direct intervention to eliminate the threat.
The years progress, and Jimmy's release from prison shatters any sense of security as he attempts to reclaim his power among the Teamsters, embroiling himself in chaos that endangers him even further. The narrative pivots to 1975, where Frank's loyalty is put to the ultimate test when he's tasked with carrying out a shocking order against Hoffa.
In a heartbreaking climax, Frank executes the very man who had once elevated him in the ranks of organized crime. The aftermath of Hoffa's disappearance sends shockwaves through the nation, forever altering Frank's family dynamics—most notably, Peggy, who begins to understand her father’s involvement in the tragedy.
The film then navigates through the web of consequences that ensue, including arrests of Frank and others, leading up to the eventual death of Russell, leaving Frank isolated and resigned to his fate. The present-day strips him of his dignity, as he confronts the alienation from his family, particularly Peggy, who cannot bear to face him.
In his final days, Frank reflects on his choices surrounded by the ghosts of his past, hoping for family connections that seem irrevocably severed as he prepares for death. His story serves as a haunting reminder of the high costs associated with a life woven deeply into crime and betrayal.
As a poignant closing note, Frank clings to a fragile hope, asking the orderly to leave the door open in quiet desperation, yearning for a visit from a family member, a glimmer of connection in his twilight.
