The Rat Pack

During a period when Dean Martin's solo success was at a peak and Sinatra's career continued to rise, Sammy Davis Jr. was rebuilding his own career and health after the car crash that cost him an eye. Joey Bishop was trying to break in with opening acts, while the Rat Pack begins to operate as a unified unit. Peter Lawford's addition cements the group's cohesion and expands their influence.

Sinatra develops a genuine interest in John F. Kennedy's political goals and sees how a White House connection could boost his own public image. He arranges for the Rat Pack to perform at a JFK campaign fundraiser, turning entertainment into a tool for political influence.

Sinatra introduces Marilyn Monroe to Kennedy, hinting at Kennedy's dalliances behind Jackie Kennedy's back. Monroe begins seeing the president, complicating the Kennedys' personal life and the Pack's political plans.

Joseph P. Kennedy worries that Sinatra's mob ties could jeopardize Jack's bid for the presidency. He asks Sinatra to work behind the scenes and to leverage those connections to win West Virginia unions' support, deepening the alignment between entertainment and politics. In parallel, the Pack's collaboration on stage grows closer to political power, and their ties extend toward a potential Ocean's 11 project.

The Rat Pack's stage shows merge into a single, high-profile act, with all members performing together and feeding off each other's charisma. Their off-screen chemistry leads to talks of a movie collaboration, ultimately giving birth to Ocean's 11. The alliance signals a powerful intersection of entertainment and politics that the public sees as a new kind of influence.

Sammy Davis Jr. endures racist jokes during their stage performances, and his fiancée May Britt hints that the others laugh at him rather than with him. He daydreams about scaring away protesters with a song-and-dance routine in a gun-toting fantasy, but he recognizes the political consequences of an interracial marriage. He postpones the wedding to avoid hurting Sinatra, who had agreed to serve as best man.

In a bid to cement friendship, Kennedy seeks to renew ties and plans to stay at Sinatra's Palm Springs residence during a West Coast trip. They go sailing together, and Sinatra is thrilled by the idea, immediately starting to build a guest compound to host Kennedy and his entourage. The arrangement demonstrates how intimate celebrity-politics links are becoming.

The FBI uncovers a potential mafia link to the White House through Judy Campbell, who had contacts with both Kennedy and mob boss Giancana. Robert F. Kennedy insists that the President cancel his stay at Sinatra's house and cut ties, enraging Sinatra and widening the rift with Lawford. The episode threatens the entire entertainment-political alliance that has formed around the Rat Pack.

Peter Lawford becomes the reluctant go-between, bearing news to the Kennedys and carrying a heavy burden of secrecy. He dreads delivering bad news and grows tired of the constant political maneuvering. Sinatra's rage peaks when he throws Lawford out of his home, signaling a decisive break in their once-tight alliance.

The incident marks the start of the Rat Pack's decline in political influence and in their on-screen collaborations. The group fractures as tensions spill into the public eye, and their once-dominant aura fades in both entertainment and politics. The film presents this moment as the turning point from a powerhouse ensemble to a fractured legacy.