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Sam Giancana (John Turturro) and Phyllis McGuire (Mary-Louise Parker) were the un-American mobster and the All-American songbird. Theirs was one of the most extraordinary and unexpected love affairs of the 60s. a relationship that rocked the nation - and shook the mob to it's core. When Vegas mobster Sam Giancana falls for singer Phyllis McGuire, it's no ordinary love affair. Apparently unaware of Giancana's mob connections, Phyllis is quickly seduced by the charming, soft-spoken gentleman. But while their love shines bright, there are storm clouds gathering, Giancana meets with the CIA and agrees to kill Castro, if they will get the mob-busting Kennedys off his back. Meanwhile the FBI is using his relationship with Phyllis to shake down the mob, photographing and wiretapping the couple's every move. Something has to give, and with their affair exposed from coast to coast, Sam and Phyllis soon find that not only her career - but his life - is in danger.