Giuliani: Son of a thug, two estranged kids, three marriages

"There are complexities in every family in America", says Rudy Giuliani. But the man called "America's mayor" by Oprah Winfrey has a more complex family than most. For a start, his father, Harold Giuliani, spent 18 months in Sing Sing prison for robbing a milkman at gunpoint in 1934. Harold later worked for relatives with mob connections, wielding a baseball bat to make sure that bar tabs were paid.

Giuliani himself, who later won his reputation as a mafia-busting attorney, married Regina Peruggi, his second cousin (though apparently he didn't know that at the time), in 1968.

He now lives with his third wife, a pharmaceutical sales manager called Judith Nathan who helped him during his struggle with prostate cancer.

His marriage in between, to Donna Hanover, ended when he announced their separation at a press conference in May 2000. Somewhat callously, he had neglected to tell her first.

Hanover is a television news anchor who branched out into acting. She has had roles in The People vs Larry Flynt, Sex and the City, and was the lead in celebrated feminist play The Vagina Monologues. The couple had two children: Andrew, in 1986, and Caroline, in 1989.

Of the pair, Andrew has had a higher public profile, ever since he played a supporting part as a baseball-playing toddler in his father’s saccharine 1993 campaign commercial. The next year, when Giuliani was inaugurated as Mayor of New York, Andrew was there beside him, reveling in the attention as he swung his podgy arms around and mimicked his father's repeated slogan of "It should be so, and it will be so". The scene was even lampooned on Saturday Night Live.

Now an aspiring golfer at Duke University, Andrew has pointedly remarked: "I got my values from my mother." His sister Caroline, who is destined for Harvard and a keen actress, caused brief controversy when journalists discovered that her Facebook page announced her support for Barack Obama's. Neither sibling sees much of their dad these days – don't expect hugs on the campaign trail.

FIRST POSTED JANUARY 28, 2008