This topic may open a whole new can of worms for the former Mayor, and likely ruin his Presidential hopes:

Giuliani’s Mistress Used N.Y. Police as Taxi Service

Although she’s now Mrs. Giuliani III, back in early 2000, while Married to Donna Hanover, Mr. Mayor was having his trysts with Judith Nathan. Personally, I do have a problem with this: a “conservative Republican” cannot run a campaign hoping to capture Values voters – regardless that there are some unfortunate Evangelical leaders backing the ex-Mayor. But there’s another twist behind the tryst: The NYPD billed an obscure City agency newly created back then by the Mayor. The question is – Why?

We all know that Mayors require a round-the-clock security detail, specifically the NYPD (for NYC Mayors). But while all NYPD city expenses are submitted to “the city”, why go out of your way to “hide” these expenses from oversight?

Former officials told ABCNews.com the extra costs involved overtime and per diem costs for officers traveling with Giuliani to secret weekend rendezvous with Nathan in the fashionable Hamptons resort area on Long Island.

When the New York City comptroller began to question the accounting, Mayor Giuliani’s office declined to provide details to city security, officials told ABCNews.com today.

“The Comptroller’s Office made repeated requests for the information in 2001 and 2002 but was informed that due to security concerns the information could not be provided,” a spokesperson for the comptroller’s office said.

Appearing in public for the first time today, Giuliani told ABC News the accusations he assigned a police security detail to his mistress and helped to hide the expenses in the mammoth New York City budget “a pre-debate hit job.”

“I’m sorry, but I still don’t understand why they filed these expenses the way they did,” he said. OK – that’s what he says, but well before it was publicly known he was seeing her, then-married New York Mayor Rudy Giuliani provided a police driver and city car for his mistress Judith Nathan, former senior city officials tell the Blotter on ABCNews.com.

“She used the PD as her personal taxi service,” said one former city official who worked for Giuliani.

New York papers reported in 2000 that the city had provided a security detail for Nathan, who became Giuliani’s third wife after his divorce from Donna Hanover, who also had her own police security detail at the same time.

Former officials close to Giuliani say he had “zero” to do with how the police security expenses for Judith Nathan, who he since married, were accounted in the city budget.

The Giuliani campaign said it would also provide a former deputy mayor, Randy Mastro, to respond to the allegations later today.

here’s the story that’s generating buzz throughout Washington political circles.

So why do I think this may open the proverbial can of worms? Well, it comes down to his judgement.

Lets look at Kerik:

Rudy Giuliani appointed Kerik police commissioner in 2000 when he was New York mayor, and he endorsed Kerik’s 2004 nomination to head the Department of Homeland Security. Days after President Bush introduced Kerik as his nominee, however, Kerik announced he was withdrawing his name because of tax issues involving his former nanny.

Giuliani has said he should have done a better job of vetting Kerik. (Give me a break: Giuliani and Kerik have been friends for a looong time.)

Seattle Times, Dec. 14, 2004:

NEW YORK — Bernard Kerik’s nanny problem might have proved the least of his troubles if the Bush administration had pressed ahead with its nomination of him to become secretary of homeland security.

The past few days have seen news reports about a rash of possible personal and professional improprieties on the part of the former New York City police commissioner, including big stock-option windfalls, connections with people suspected of doing business with the mob and, yesterday, allegations he had simultaneous extramarital affairs with two women.

…The newspaper Newsday reported that investigators conducting a background check of Kerik last week uncovered that the former nominee had been married to a woman he has apparently kept a secret for the past 20 years. Friends of his said they were not aware of the woman, and Kerik did not acknowledge the marriage in his best-selling autobiography, “The Lost Son: A Life in Pursuit of Justice.”

Instead, he wrote about only two marriages, one to a New Jersey woman named Jacqueline, whom he married in 1983 when he was 28, and one to his current wife, Hala. But Kerik, who withdrew his name from consideration for the nation’s top security post on Friday, was also married to the former Linda Hales in North Carolina.

(Remember – Giuliani pushed the White House to nominate Kerik)

Citing unidentified sources, the New York Daily News said Kerik had overlapping affairs with Judith Regan, the publisher of his recent memoir, and a city corrections officer. He used the same New York City apartment for liaisons with the women during his 18-month tenure as head of the nation’s largest police department, ending in 2001, the paper said.

Yesterday, Kerik said he wanted to apologize “to anybody who’s been brought into this unnecessarily,” including Regan and former Mayor Rudolph Giuliani, a close friend and business associate who had promoted the former street cop’s Cabinet candidacy.

…Other recent reports claim that around the time of the alleged affairs, Kerik accepted unreported gifts of thousands of dollars in cash and other items from associates at a New Jersey construction company while serving under Giuliani, first as corrections chief, then as police commissioner.

Lastly, I found an interesting piece of information too: In today’s World Net Daily commentary by Jane Chastain titled President Giuliani: My worst nightmare: she pens: “Giuliani is a liberal with a few conservative tendencies – very few. In 1988, Rudy’s mother, Helen, said, “He only became a Republican after he began to get all these jobs from them. He’s definitely not a conservative Republican.” This from his Mom!