Skip to content, or skip to search.

Skip to content, or skip to search.

Tears of a Cop

The one thing Kerik says he didn’t discuss with the White House is what he calls the “gossipy stuff,” his affairs with Jeanette Pinero, a Corrections officer, and with book publisher Judith Regan. Though he is still friends with Pinero, his romantic involvement with her ended, he says, before his marriage in 1998. His involvement with the mercurial Regan, however, is more complicated.

Their apparently stormy relationship began during work on his best-selling book, The Lost Son, which Regan published, and it played out in Kerik’s waning days as police commissioner. Since then, Kerik has publicly taken the high road. He will say only that they became close during the work on his memoir and that she always conducted herself in a professional manner.

People close to Kerik, however, say that he ended the relationship and that Regan, who is not someone to be trifled with, was furious. They claim that, once Kerik withdrew his name from consideration, she leaked information about him. Stories have been floated that he harassed her, bugged her car, caused her to fear for her safety, and, of course, that at least one of their romantic liaisons took place in an apartment overlooking ground zero. (Regan declined to comment.)

Kerik says that there were a handful of apartments set aside for Police and Fire Department brass who were working round the clock, often sleeping in their offices. The idea, he says, that they were for rescue workers is patently ridiculous. “How would that’ve worked? There’d be hundreds or even thousands of workers waiting in line to use one of these apartments to shower or get some sleep.” Nevertheless, the symbolism here is overwhelming.

As Kerik talks about some of the charges that have been leveled against him, his mood begins to darken. At some point I notice that he has turned sideways in the chair, with one leg hanging over the arm. Sunlight is streaming in through the wood blinds, shining brightly on half of his face, with the other half in shadows.

“After 30 years of public service,” he begins haltingly, “after 30 years of fighting injustice and risking my life, to now have people mock that 30-year career based on lies, exaggerated innuendo, and all of this Fahrenheit 9/11–connect-the-dots stuff . . . I trained my whole life for this, fighting drug dealers, getting in gun battles, going to Iraq, living through 9/11.

“Several times that day I really didn’t think I was gonna make it out. I was standing across the street from the North Tower when the second plane hit. I remember Hector Santiago dragging me up the block by my belt. All kinds of shit was raining down on us. An airplane wheel fell right in front of us. Hector got hit with something in the back of his leg. And then the dust and the gas when we were trapped inside 75 Barclay Street. To live through all the stuff I’ve done in my life and to lose this opportunity . . . ” His voice trails off, and he looks out the window. Tears are streaming down his cheeks.

There is an excruciating minute-long silence. “Whether my nanny had legal status or not had nothing to do with the kind of job I was going to do,” he says, regaining control. “Then people use these opportunities to attempt to destroy you. They don’t have the courage to stand up to you face-to-face. None of this handful of people—and that’s all it is, maybe five or six people—had the balls to attack me until I’d withdrawn. For the first eight days, no one came forward.”

But Kerik knows that what happened was ultimately his own fault. There is no one to blame. Were there unfair stories written about him? Absolutely. Were some things blown up or taken completely out of context? No question. But he is keenly aware that he opened the door with his behavior. If his judgment had been more consistent, if he hadn’t played so fast and loose with the rules, none of the other stuff would’ve stuck.

“I know I fucked up,” he says flatly. “I made some major mistakes, and they catch up to you. I didn’t focus enough on ethical issues. But I still believe that my successes over my 30-year career outweigh the errors in judgment.”

Of everything he’s been accused of, the thing that bothers him the most, the charge that really eats at him, is the claim that he’s connected to organized crime. “I’m as close to organized crime as I am to Saddam Hussein,” he says. “It’s ridiculous.”

The accusation is based on two distinct but obliquely related episodes. The first centers on Larry Ray, who was the best man at Kerik’s wedding in 1998. In the mid-nineties, Ray and Kerik were fast friends. Ray seemed to be really plugged in. He introduced Kerik to a wide range of people, including Mikhail Gorbachev, Christie Todd Whitman, and Jim Florio. One of these introductions was to a guy named Frank DiTommaso, owner of a construction company called Interstate Industrial.

Interstate, which was the object of a series of investigations in New York and New Jersey for alleged ties to organized crime, sought a big contract at the time with the city. When DiTommaso was looking for help handling the investigations—one by the city’s Trade Waste Commission and the other by New Jersey’s Casino Control Commission—he hired Larry Ray.

But while it has been widely reported that DiTommaso hired Ray after Kerik vouched for him—“He’s a top-shelf guy,” was Kerik’s description—DiTommaso says this is not true: “I had been good friends with Larry Ray for years,” he says. “Why would I need Kerik to vouch for him? I gave sworn testimony about this that has been taken totally out of context. When Kerik said Larry was ‘top-shelf,’ we were just making small talk. I didn’t decide to hire Larry until much later.” He also hired Kerik’s brother.

Worse was that Kerik, who has a history of money problems, accepted gifts from Ray while he was Corrections commissioner and didn’t report them. Ray and another friend kicked in $10,000 for Kerik’s wedding reception at the Chanticler catering hall in Short Hills, New Jersey, in 1998. He also bought Kerik over $4,000 worth of Bellini baby furniture when Kerik’s daughter was born.

Ray turned out to be a kind of high-level con man who pleaded guilty to a felony charge of stock fraud. When he got in trouble, he asked Kerik for help. But Kerik, by then police commissioner, cut him off. Ray, who felt like Kerik owed him, was angry when he got the cold shoulder and began speaking out. “I felt, with everything I have learned,” Ray told the Daily News about Kerik in December, “that he would disgrace the country and the office of the president.”

Kerik says the White House knew all about his relationship with Ray. A staffer who called Kerik during the vetting process was a former federal prosecutor in the Eastern District, where Ray was indicted. Kerik’s bad judgment with Ray makes it believable that something may have been amiss in his relationship with DiTommaso as well, and—you have to connect the dots here—that he was somehow tied to the mob. The city Department of Investigation is looking into the unreported gifts from Ray.