Judith Exner
One of the president's most scandalous mistresses (and the one Jackie certainly wanted to keep out of the press) was Judith Exner, a mafia chick who was introduced to Kennedy in 1960 by Frank Sinatra (in Las Vegas, no less). The drama here (besides the whole cheating thing) was the fact that she was involved with Chicago mob boss Sam Giancana. During their years-long dalliance, Exner claimed to have transported packages between the two.
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