The film traces the peak years of the Rat Pack, centered on Dean Martin, Sammy Davis Jr., and Joey Bishop as they ride a wave of fame through the late 1950s and early 1960s. Martin thrives on his own, Sinatra’s star keeps rising, and Davis, after a devastating car crash that cost him an eye, begins a long road to recovery, while Bishop works to break through with opening acts. The group comes together around Peter Lawford, who has been sidelined by public knowledge of his ties to Sinatra’s former wife, Ava Gardner. Lawford’s marriage to Patricia Kennedy adds another layer of complexity, while Sinatra grows increasingly drawn to John F. Kennedy and his political ambitions, hoping proximity to the White House will boost his own image.
Sinatra arranges for the entire Pack to perform at a Kennedy campaign fundraiser and quietly introduces Kennedy to Marilyn Monroe, who begins seeing Kennedy behind the back of her husband, baseball icon Joe DiMaggio. The movie also narrows in on Kennedy’s father’s concerns about mob ties, urging Sinatra to stay in the background while still leveraging unions to support Kennedy’s bid. The alliance deepens as the two sides collaborate on performances and even consider a future project together, echoing their real-life collaboration on Ocean’s 11.
Davis, meanwhile, faces moments of painful racism within the act, especially after his girlfriend, May Britt, signals that the rest of the Pack is laughing at him rather than with him. He postpones his wedding to Britt to spare Sinatra, who had promised to stand as best man, but the weight of public scrutiny remains. In the White House, Kennedy seeks to renew friendship with Sinatra, and the two men imagine a closer connection, planning for Kennedy to stay at Sinatra’s Palm Springs residence during a West Coast swing. Sinatra even renovates a guest compound to accommodate Kennedy and his entourage, a gesture that intensifies attention from federal investigators.
The FBI uncovers a potential mafia link to the White House through Judy Campbell, who shared calls and possible affairs with both Kennedy and mob boss Momo Giancana, following an introduction by Sinatra. Kennedy’s brother, Attorney General Robert F. Kennedy, urges the President to cancel the visit and sever ties with Sinatra, a decision that enrages Sinatra who had invested heavily in the arrangement. Lawford finds himself repeatedly serving as a messenger between Sinatra and the Kennedys, including revelations about Kennedy’s secret dalliances with Monroe, and he grows weary of the ongoing strain. A frustrated Sinatra ultimately throws Lawford out, marking what many viewers see as the beginning of the end for the Rat Pack’s influence in both politics and entertainment.
