JFK Campaign Support

Lore & Background

Sinatra's role went beyond public endorsement. He is reported to have served as a liaison and intermediary between Kennedy and Chicago Outfit mafia boss Sam Giancana. Chicago FBI agent William F. Roemer recalls that during one of his surveillance operations, Giancana's underling Chuckie English came to his car with a message from Giancana: "He says if Kennedy wants to talk to him, he knows who to go through." When Roemer asked if he was speaking about Sinatra, English affirmed it. According to Sinatra's daughter Tina, Kennedy's father Joseph P. Kennedy Sr. approached Sinatra in order to get Giancana to secure the trade union vote for Kennedy in the West Virginia primary election, which he agreed to do. Sinatra also produced the January 19, 1961 Inaugural Gala that raised millions.

In Their Own Story

The air inside the opulent suite hummed with jazz and the clinking of crystal glasses, a stark contrast to the tense political atmosphere outside. Sinatra stood at the center of the room, his tuxedo sharp, holding court over a gathering of the city's elite. He spoke not of policy, but of vision, his voice dropping to that familiar, intimate baritone that could sell a dream as easily as a song. In the corner, Kennedy listened intently, watching as the Rat Pack's charm turned skeptics into believers. It was in moments like these, amidst the smoke and laughter, that the future of the nation seemed to pivot on the charisma of a singer.

Reader's Guide

The arc begins with Sinatra deciding to back Kennedy early in the primary season. He immediately mobilizes his circle of friends, known as the Rat Pack, to tour for JFK. Sinatra rewrote "High Hopes" and commissioned Sammy Cahn lyrics for the campaign. According to Sinatra's daughter Tina, Kennedy's father Joseph P. Kennedy Sr. approached Sinatra in order to get Giancana to secure the trade union vote for Kennedy in the West Virginia primary election, which he agreed to do. Sinatra is reported to have served as a liaison and intermediary between Kennedy and Giancana. The impact culminates in the general election, and Sinatra produced the January 19, 1961 Inaugural Gala that raised millions.

Did You Know?

• Sinatra rewrote the song "High Hopes" and commissioned Sammy Cahn lyrics for Kennedy's campaign.
• Sinatra produced the January 19, 1961 Inaugural Gala that raised millions.
• According to Sinatra's daughter Tina, Joseph P. Kennedy Sr. approached Sinatra to get mafia boss Sam Giancana to secure the trade union vote for Kennedy in the West Virginia primary.
• Chicago FBI agent William F. Roemer recorded that Giancana's underling said Kennedy could reach Giancana through Sinatra.