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New York Postcard

Bad Cop

The DiTomasso brothers may not have much in common with George W. Bush, but there's one thing the president and the mob-linked contractors share: Both have reason to rue the day they met Bernard B. Kerik.

In 2004, Bush nominated Mayor Rudy Giuliani's former police commissioner to head the Department of Homeland Security (DHS). Within days, allegations surfaced that Kerik had faced arrest for unpaid bills, had close ties to some federal contractors, and had failed to pay taxes on his nanny. The nomination collapsed, calling the White House's judgment into question. In 1999, in what may have been an attempt to win city contracts, the DiTomasso brothers renovated Kerik's Bronx apartment for free. When a Bronx grand jury called the DiTomassos, they allegedly lied about it. "They were trying to protect him," says Leonard Levitt, whose nypd Confidential website is the first stop for police gossip. "They're indicted. He goes free."

The annals of New York politics are full of nickel-and-dime schemes, venality, and outright stupidity, but Kerik's broad swath of damage is hard to match. The 51-year-old cop is not a backstabber--to the contrary, he's known for personal loyalty--but, in his long stumble down the corridors of Republican power, he has done a cartoonish mountain of damage, mostly to his friends and allies. Indictments (the DiTomassos, former aide Fred Patrick); ruined careers (former spokesman Tom Antenen); a love affair splashed across the tabloids (with publisher Judith Regan, at a city-owned apartment next to Ground Zero). Amid rumors of an investigation, his former chief of staff reportedly decamped to Brazil, where he apparently tried to sell a Kerik official windbreaker for $1,000 on eBay. "He's like Kryptonite," says Levitt. "Anybody he's had anything to do with comes away screwed and bitter."

But one Kerik friend remains unscathed: Giuliani. Kerik, in many ways, is a creation of the former New York City mayor, who helped him rise from the middle level of the police department to fame and notoriety. But, now that Giuliani is presumably making a run for the presidency in 2008, his friendship with the toxic Kerik may be his greatest liability. So far, Giuliani has managed to keep Kerik close while avoiding the kiss of death that has sunk so many of his former aide's other friends. But the latest Kerik scandal threatens to consign Giuliani to their same fate.

Kerik has been with Giuliani since the beginning. According to Kerik's autobiography, The Lost Son, he admired Giuliani's 1989 mayoral campaign to restore law and order, having met the future mayor at an event honoring a slain police officer. Kerik was an nypd detective--an aggressive tank of a man known as "Mustache" for his trademark facial hair. He volunteered to help in Giuliani's reelection campaign four years later, becoming the mayor's bodyguard and driver.

Kerik fit the mold Giuliani preferred: intensely loyal men from modest, white ethnic backgrounds like his own. After Giuliani's victory, Kerik took a high-ranking post in the Department of Corrections, despite his lack of management experience. He later ran that department and is thought to have done a good job. Then, in 2000, Giuliani picked Kerik to run his beloved NYPD.

Kerik has always been tough enough to pull himself up by his bootstraps but boneheaded enough to fall over his own feet. He grew up in inner-city Paterson, New Jersey, the son of an alcoholic prostitute who abandoned him when he was four. (She was later killed.) After dropping out of high school, he made his way into the Army and seemed to be rising in the ranks until another soldier insulted him. "He stuck his middle finger right in my face," Kerik wrote in his 2001 autobiography. "So I broke it."

Before long, Kerik was a street cop with a reputation for dedication and a willingness to break the rules. Those qualities followed him into city government. In one notorious episode as police commissioner, he violated city bidding procedures, spending $50,000 each on four security doors for police headquarters. They were put in storage after proving too heavy for the floor to support. But he also got headlines for going out and making busts himself--something he repeated in 2003, when Bush sent him to Iraq. His physical courage was never in doubt, and he was one of the iconic figures on September 11. When Giuliani left office in January of 2002, he took Kerik with him to head the security arm of his sprawling new firm, Giuliani Partners.

But, after the debacle of the Homeland Security appointment, Rudy did the politic thing and dumped his troublesome protege. Kerik quietly resigned and set up his own security firm, conveniently located in the office of his criminal defense lawyer. Kerik, however, wasn't done bringing down his friends. In the summer of 2005, he took a call from Jeanine Pirro, the hapless Westchester district attorney who had dropped out of the U.S. Senate race to run for New York attorney general. Pirro suspected her troublesome husband, Al, of having an affair (yet another), this time with one Lisa Santangelo. She asked Kerik to bug Al's boat. "We can just simply say, if there is an issue, that I am redecorating it for our anniversary," Pirro said.

Kerik demurred: "But Jeanine, I'm having the same fucking problem with everybody. Everybody is panic stricken because it's you. I've gone out on a limb. I had two other people looking at this." "What am I supposed to do, Bernie?" Pirro asked. "Watch him fuck her every night? ... I'll put the fucking thing on myself."

We have this exchange, of course, because Bronx prosecutors, interested in the DiTomasso's undisclosed renovations on Kerik's apartment, tapped Kerik's phone. On September 27, 2006, half an hour after WNBC aired news of the leaked transcript, Pirro appeared at a press conference so rattled that she left her wad of chewing gum stuck to the inside of the podium. The Kerik Kryptonite had struck again, diminishing Pirro's already slim chances of becoming attorney general and prompting a new federal investigation--this time, into her.

The Pirro scandal shows signs of coming full circle back to Kerik's mentor, Giuliani. Kerik's first call after his conversation with Pirro was reportedly to Giuliani Partners. The Daily News has reported that prosecutors have expressed interest in one current and one former employee of a Giuliani Partners subsidiary for their roles in the Pirro case--and that one has already been subpoenaed to testify before a grand jury. And the as-yet-unleaked reams of Bronx wiretap have fueled endless speculation about what Giuliani may have said. "You've got to believe he's on those wiretaps," speculates Doug Muzzio, a professor of public affairs at the City University of New York. "This is not good for business, and it's not good for his presidential race."

People around Giuliani say they don't know what the damage will be. "It depends on what's on those tapes," says one former aide. Giuliani's spokeswoman, Sunny Mindel, declined to comment on whether Giuliani called Kerik in 2005, when prosecutors were reportedly listening in.

But, despite the fact that Kerik may drag Giuliani's name into the seamy world of illegal wiretaps and mafia-linked contractors, it's still unlikely Giuliani will cast him out. Giuliani's attachment to his former driver reveals what has always been a defining quality about the likely presidential contender: Giuliani expects deep loyalty, and returns it to his aides and their families with little attention to their qualifications. Despite Kerik's symbolic expulsion from Giuliani Partners after the DHS fiasco, Giuliani has never repudiated his former bodyguard. That's not how things work within his tight, intensely loyal inner circle.

On September 11, Giuliani hosts an annual dinner, a blend of reunion and memorial for his City Hall circle. This year it was at Frank's, a steakhouse in the meatpacking district, and two people who were there were mildly surprised to see the hulking shoulders and trademark mustache. Kerik, who had pled guilty to misdemeanor charges for accepting the free renovations two months earlier, wasn't doing much talking. He was "on an island amid a sea of people," said one guest. But he was there. When I expressed surprise to Giuliani insiders that the tarnished Kerik had been invited to that September 11 dinner, they just shrugged. Kerik, one said, is "part of the family."

Ben Smith is a political journalist and blogger for Politico.