Judi Ann Stish trained to be a nurse, but never got to the tending-to-patients part: Several months after finishing school, a 19-year-old Judi tied the knot with to her first husband, a surgical supply salesman named Jeffrey Scott Ross. She soon joined Ross on the sales trail, marketing surgical staples to doctors and demonstrating the product on mildly-sedated stray dogs, a process that involved removing their organs and then pumping them full of liquid to show that the staples were effective. (The company, not surprisingly, was later besieged by animal cruelty groups.) In 1979, Judi divorced Ross; five days later, she married a wallpaper dealer named Bruce Nathan, and when that union didn't last, she returned to the job force. It was in 1999, while she was sharing a fold-out bed with her boyfriend at the time, psychologist Manos Zacharioudakis, that Nathan reeled in her biggest fish yet. She approached Mayor Giuliani, who was then married to Donna Hanover, at the cigar bar Club Macanudo with her business card in hand. Following a year-long affair, Giuliani came clean about the romance in 2000. A very public, acrimonious divorce ensued and it took nearly three years for the ex-mayor to tie the knot with Nathan. On May 24, 2003, the couple married on the lawn of Gracie Mansion.
Of course, few knew much about Nathan—or her checkered past—until 2007 when Rudy decided to pursue the presidency. Nathan campaigned by his side during his quasi-disastrous run, helping him with his (Sept. 11th-exploiting) speeches and serving as his esteemed expert on "biological and chemical" disasters. She was even on the campaign's payroll, earning $125,000 a year for her services. Her efforts to insinuate herself into the campaign didn't go over well with a number of the former mayor's staffers, and she also emerged as a liability for Giuliani after a number of embarrassing disclosures, such as her admission that Rudy was actually her third husband and not her second, as had been previously reported. More humiliation followed the revelation that she had a full-time, Frédéric Fekkai-trained hairstylist who traveled with her everywhere and always insisted on a extra seat aboard private jet trips so her handbag (or her "Baby Louis," as she preferred to call it) could travel in style. She's kept a lower profile since then, mostly sticking to the charity circuit with organizations like the Twin Towers Fund. [Image via Getty]