Which entertainer acted as a liaison between the Chicago crime family and the Kennedys?

Answer Frank Sinatra

Ol' Blue Eyes notoriously had connections with the mob. In the '60s, Frank Sinatra worked as a liaison between the Kennedy family and the Chicago mob boss, mainly to push Union backing. Kennedy went back on his promise when elected, but luckily the mob didn't shoot the messenger and, instead, just forced Sinatra to perform for eight nights at the club.

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