If anything can expose a chink in Rudy Giuliani’s armor, criminal charges against his one-time police commissioner might do it.

Giuliani, the former New York mayor, has hung on as the front-runner in the Republican presidential race, defying predictions that his moderate record and three marriages would repel conservative primary voters.

Now, his erstwhile protege Bernard Kerik may face federal criminal charges including tax evasion and corruption. The case against Kerik — a friend, business partner and former police commissioner of Giuliani’s — is an opportunity for critics to question Giuliani’s judgment.

“Rudy Giuliani has a few Achilles heels, and Bernard Kerik is definitely one of them,” said Tobe Berkovitz, interim dean at Boston University’s college of communications. “The question is, can one of his opponents capitalize on it?

“The mainstream media absolutely will capitalize on it, they’ll pounce, and then it’s really going to demonstrate how good is Rudy Giuliani as a politician, and how good is his campaign, in how he responds to this,” Berkovitz said.

So far, Giuliani has said he made mistakes in dealing with Kerik, whom he pushed to head the federal Department of Homeland Security. But Giuliani has asked that people look at his overall record in New York, where he cut crime, reduced taxes and trimmed welfare rolls.

“It was a mistake not checking him out as thoroughly as I should have,” he said Monday in an interview with The Associated Press.

“I made mistakes. I will continue to make mistakes,” Giuliani said. “But what are the results? What kind of results do I get? What Bernie Kerik did wrong did not implicate what the results were for the public. What he did wrong, he’s going to have to pay for.”

Kerik was to surrender Friday to federal authorities in White Plains, N.Y., for arraignment on criminal charges. Authorities have alleged Kerik took tens of thousands of dollars in services from benefactors and never reported it as income. Kerik rejected a plea deal earlier this year, his attorney insisting he did nothing wrong.

Kerik and Giuliani were friends for years; Kerik rose from Giuliani’s driver during his 1993 mayoral campaign to head of the city’s corrections department and commissioner of police. He later joined Giuliani’s firm, Giuliani Partners, and headed an affiliated security consulting company, Giuliani-Kerik.

Controversy surfaced when President Bush nominated Kerik as Homeland Security chief in 2004. Kerik abruptly withdrew his name because of tax issues involving his former nanny. News reports also had surfaced about stock-option windfalls, connections with people suspected of dealing with the mob and extramarital affairs.

Kerik pleaded guilty last year to state charges of accepting $165,000 in renovations to his Bronx apartment from a construction company, allegedly connected to the Mafia and trying to secure city contracts.

Democrats argue that Giuliani’s tough-on-crime image is at odds with his longtime relationship with Kerik.

“Voters are going to question Rudy Giuliani’s judgment given that he shepherded Kerik’s career while he knew there was an ethical cloud over his head,” said Democratic National Committee spokesman Dag Vega.

Critics question Giuliani’s loyalty to Kerik and other friends; Giuliani has kept his childhood friend, former Monsignor Alan Placa, on the payroll of his consulting company; Placa was barred from the ministry after being accused of sexual abuse himself and of helping cover up abuse by other priests.

Republican consultant Whit Ayres said the Kerik case might tarnish Giuliani’s armor rather than inflict any lasting damage.

“It’s an embarrassment,” Ayres said. “Isolated problems with individual supporters are never a major problem unless they become a pattern.”

He mentioned the resignation earlier this week of an adviser to Republican Fred Thompson, Philip Martin, after a report surfaced about Martin’s decades-old criminal record for drug dealing.

The episode was basically a one-day story for Thompson, Ayres said, although he acknowledged the Kerik case could stick around a little longer, considering Giuliani recommended Kerik for the Bush Cabinet.

In Associated Press-Ipsos polling released Thursday, Giuliani was ahead of Thompson 29 percent to 19 percent, about the same statistically as his 27 percent to 23 percent advantage last month.

“Anything that extends the story becomes more challenging,” Ayres said. “They’ll try to use this to embarrass him and scuff up his reputation as a fine manager, but it’s hard to imagine this being a silver bullet. It’s just not that big a deal in the great scheme of things.”

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