Just as Robert J. McDonnell served as a go-between in the earlier 
contact with the Chicago mob, Kennedy’s mistress Judith Exner would play 
the same role now. Since Exner was having an affair with Sam Giancana at 
the very same time she was sleeping with JFK, she was made to order. 
Exner became a bagwoman for Kennedy during the 1960 campaign, taking up 
to $250,000 in cash to Giancana on trips to Chicago. These payments were 
intended as bribes for trade union bureaucrats that Giancana and 
Humphreys had lined up. Eventually Exner would split up with Kennedy 
when he showed up at one of their trysts with another woman for a threesome.

full: http://louisproyect.org/2013/11/22/remembering-jfk/
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