The honors have to go to the 16-year-long, madly passionate affair between Sam Giancana, the evilest, cruelest, nastiest and ugliest gangster to run the Chicago mob since Al Capone, and the beautiful Phyllis McGuire, one of the McGuire Sisters, the white-glove-glamorous superstar singing trio of the 1950s and '60s.

Which mobster did Phyllis McGuire date?

Phyllis McGuire, the last of the popular McGuire Sisters singing trio and onetime girlfriend of Chicago Outfit boss Sam Giancana, died December 29 at her Las Vegas home. She was 89.

Which McGuire sister was married to a mobster?

Phyllis, who had been married once in the 1950s, was single and raising eyebrows. Rumors began circulating, and then were confirmed without apology by Ms. McGuire, that she was the girlfriend of Chicago mob boss Sam Giancana. They had met in 1959, when Ms.