Kerik did not fit the button-down model of the Bush administration. A high school dropout and son of a prostitute apparently killed by her pimp, Kerik became an undercover narcotics detective with ponytail and diamond earrings. He joined Giuliani's 1993 campaign as his driver and was later given top appointments, including corrections commissioner and eventually police commissioner. After office, Giuliani and Kerik became partners in a security consulting firm.

So when Giuliani telephoned Bush to recommend that he make Kerik his second-term homeland security secretary, the president jumped at the idea. The sheen of a 9/11 hero seemed to be just what was needed to take on a troubled new department struggling to integrate 22 agencies and 180,000 employees to protect the nation's ports, borders and airports; enforce immigration and customs laws; and respond to major disasters. Only a few aides, including then-Chief of Staff Andrew H. Card Jr. and senior adviser Karl Rove, were clued in to the president's decision.

As with every nominee, Kerik was given detailed financial disclosure and personal history questionnaires to fill out, all intended to unearth anything that might prove embarrassing in a confirmation hearing. Giuliani's firm assisted in filling out the forms, according to a source familiar with the situation, and the papers are now an issue in the federal criminal investigation. Kerik, his attorney and Giuliani Partners spokeswoman Sunny Mindel declined to comment.

Presidential nominees typically go through a full-fledged FBI background investigation before their appointments are announced. But because it is hard to keep Cabinet selections secret for so long, they are vetted only by the White House counsel's office before being made public. The FBI then conducts its full probe before Senate confirmation hearings begin.

The counsel's vetting depends heavily on honest responses from a nominee, officials said. Yet in Kerik's case, a quick FBI search and research by the White House turned up a host of problems in the couple of weeks before the nomination was announced. According to the sources, who spoke on the condition of anonymity because of White House policy against discussing personnel matters, Bush aides discovered that:

? Kerik was fined $2,500 by New York City for using police detectives to help him with his autobiography. He was also a defendant in a civil lawsuit accusing him of retaliation against a corrections official who had disciplined a female prison guard with whom Kerik was having a relationship. Kerik was scheduled to give a deposition in the case right after his nomination was to be announced.

? One of Kerik's former top deputies was convicted of stealing money from a foundation that Kerik ran while serving as Giuliani's corrections chief. The foundation was funded by rebates from tobacco companies selling cigarettes to prison inmates.

? Kerik, who filed for bankruptcy as a police officer, became rich almost overnight after leaving office. Just before his nomination, he made a quick $6.2 million without investing a dime by exercising stock options from his service on the board of Taser International, a stun-gun firm seeking business with homeland security agencies.

? Kerik's tenure in Iraq generated strong criticism of his management. Iraqi officials complained to U.S. authorities about $1.2 billion Kerik spent to train Iraqi police officers in Jordan, spending they called wasteful. Iraqis also questioned why Kerik spent tens of millions of dollars to buy weapons for Iraqi trainees when the U.S. military had confiscated plenty of such weapons after the invasion.

"There were alarm bells all around," said a former White House official.
A Friend Accused of Mob Ties

The loudest alarm bell was Kerik's relationship with Lawrence Ray. The best man at Kerik's wedding in 1998, Ray went to work for a New Jersey construction company, Interstate Industrial Corp., that was seeking a big New York City contract and trying to overcome concerns inside Giuliani's administration that it had mob ties.

Ray, who told friends that he worked with the FBI, military and intelligence agencies in the 1990s, was indicted in 2000 along with organized-crime figures in what prosecutors described as a scheme to manipulate the stock market. He pleaded guilty and was spared prison time.

The White House had the perfect person to question Kerik about his relationship with Ray: Julie Myers, who arrived in the White House personnel office in November 2004 and had worked in the same U.S. attorney's office in Brooklyn that prosecuted Ray. She flagged the relationship and other concerns about Kerik for her White House colleagues, sources said. She aggressively questioned Kerik about Ray and other affiliations. He bristled at her tone, sources said.

In an interview last week, Ray said he had told the FBI and U.S. attorney's office as early as 1999, as he tried to stave off indictment, that he had incriminating information about Kerik. After his guilty plea in 2001, Ray said, he told the FBI that Kerik had agreed to help Interstate Industrial and its owners, the DiTomasso family, try to win city business despite their alleged ties with organized crime. At the time, Kerik solicited and received gifts from company sources, including $165,000 in renovations for his apartment.

"They knew 100 percent of it," Ray said. "There was no way they didn't. I was driving the ball on that."

Kerik told the White House that the allegations were untrue, sources said. "He was told many times, 'Be honest,' " said one person familiar with the process. Myers, presidential personnel director Dina Powell and others raised concerns in the West Wing, according to the sources. They were "very, very adamant about how serious the vetting needed to be," one source said.

Gonzales, then the White House counsel, who was about to begin his own confirmation process for attorney general, took charge of questioning Kerik, grilling him for hours on several occasions, the sources said. At one point, Gonzales called while Kerik was having lunch at a New York steakhouse and talked to him on his cellphone for an hour and a half. Nanette Everson, then the White House ethics counsel, was kept on the sideline for the heavy-duty part of the vetting.

But in the end, White House officials knew that Kerik had been head of the nation's largest police department and had a security clearance for his work in Iraq. He was a hero of Sept. 11. He was well liked by the president. No one checked with key officials at the Homeland Security, Defense or State departments or elsewhere in the government. Even within the White House, the choice was kept secret so Bush could make a splash.

"The loop on it was extremely small," said a former official. "That's a president-of-the-United-States, 'I don't want anyone to know, I want to announce it on Friday' [deal]. It drives people to not follow all the normal procedures."

Bush summoned Kerik to the Oval Office for a perfunctory interview Dec. 1 and, without asking any policy questions, asked if he wanted to be homeland security secretary. Kerik accepted. "He told me he wanted someone to go in there and 'break some china,' " Kerik later told New York magazine. Kerik walked out and called Giuliani to tell him the news. Two days later, Bush and Kerik appeared together to make the nomination public. Only then did the china start to break.
The Past Comes to Light

The initial reviews were positive. New York's Democratic senators, Hillary Rodham Clinton and Charles E. Schumer, issued laudatory statements. But from corners of Washington and New York, calls began pouring in to the White House and to newsrooms.

Stories began circulating about Kerik's time in Iraq, about an arrest warrant issued when he failed to respond to a civil lawsuit, about his extramarital affair with book publisher Judith Regan, about his trysts in a city apartment meant as a place for police officials to rest near Ground Zero. Ray went public with his allegations about Kerik's gifts from the DiTomasso family. Kerik and the White House tried to ride it out. Giuliani advised Kerik through the political storm.

But then people at the Giuliani firm who were scouring Kerik's finances discovered that he had not paid Social Security taxes for a nanny who apparently was an illegal immigrant, Kerik later said. By Kerik's account, Giuliani told him he had to call the White House, and by the end of the day on Dec. 10, they agreed he had to pull out. Statements were issued after the evening news, and Giuliani came to console his friend.

"I made some major mistakes, and they catch up to you," Kerik told New York magazine a few months later. "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." Except for the nanny, he said, "everything that's come out is stuff I either told the White House about or they already knew."

But more was to come. After Kerik withdrew, Ray became the central witness in several investigations. The New York Department of Investigation and the Bronx district attorney's office opened probes into Kerik's gifts using wiretaps, grand jury testimony and numerous e-mails Ray gave them.

In the e-mails, Kerik appears to be soliciting Ray for money. "I was going to ask you if we had between 18 and 2,000 available," Kerik wrote in 1999. Another time, Kerik mentioned financial difficulties and the apartment. "I've got to make sure we can do the renovations," he said. Sources familiar with the investigation said Kerik may challenge the authenticity of the e-mails if federal charges are filed, but the Bronx district attorney's office authenticated the e-mails as it brought its case against Kerik, according to lead investigator Stephen Bookin.

New Jersey gambling-enforcement authorities also filed a complaint in 2005 accusing Kerik of misusing his Giuliani administration jobs to solicit gifts from the DiTomassos, who have fought allegations of mob ties, while helping them try to win city business. Kerik asserted his Fifth Amendment right not to answer some questions in the proceedings. He pleaded guilty to two misdemeanors in New York court last summer, acknowledging that he had accepted the apartment renovations.

In the White House, there is still resentment toward Giuliani for foisting the problem on the president. "There are two people who are to blame for what happened -- Rudy Giuliani and Bernie Kerik," said one former White House official. Still, a senior administration official acknowledged some responsibility as well. Bush wanted "a hard-charging personality" to get the department in line, he said. "Instead, we ended up shooting ourselves in the foot."

The latest collection of documents, the sixth batch produced by the Justice Department in recent weeks, also cast further light on the frantic scramble by the Bush administration since January to contain the public relations damage caused by the ouster of the eight.

The electronic messages, some written as recently as last month, offer a rare and almost contemporaneous account of the tactics used by a sitting administration trying to manage a political firestorm.

One e-mail message shows the White House urging the Justice Department to call Senator Jeff Sessions, Republican of Alabama, to give him information about the placement of J. Timothy Griffin, a former aide to Karl Rove, as the interim United States attorney in Arkansas.

“WH political reached out to Sen. Sessions and requested that he ask helpful questions to make clear that Tim Griffin is qualified to serve,” said a January 2007 e-mail message from Monica Goodling, a former senior aide to Mr. Gonzales, to other department officials. “Here are the talkers on Griffin, as well as a narrative that can be used by staff, and his résumé. I think it would actually be helpful for all of the Rs to have it.”

It was not clear whether the “talkers," shorthand for talking points, were sent to Mr. Sessions and other “Rs,” or Republicans. But Mr. Sessions, in a later hearing on the matter, ran through all of the highlights, praising Mr. Griffin’s résumé, just as the White House and Justice had apparently requested.

Other documents show that Ms. Goodling, the Justice Department’s liaison to the White House, prepared a list of reasons in February to explain publicly why the prosecutors had been ousted.

Notes in handwriting identified by a Justice official as Ms. Goodling’s run quickly through a list of alleged transgressions by the fired prosecutors, like “incredibly fractured office, morale low, lost confidence of her subordinates and superiors,” in describing Margaret Chiara, the former United States attorney from Western Michigan who disputes the claims.

In the case of David Iglesias, who was dismissed as the top federal prosecutor in New Mexico, Ms. Goodling writes of a complaint from Senator Pete V. Domenici of New Mexico, a Republican: “Domenici says he doesn’t move cases.”

The e-mail was among more than 2,000 pages of documents released by the Justice Department as part of a continuing outpouring of more than 6,000 pages of e-mail and other internal records produced in the last month in response to requests by House and Senate committees as the furor over the dismissals has grown. Mr. Gonzales is scheduled to appear on Tuesday before the Senate Judiciary Committee.

The Justice Department said that Mr. Sampson’s e-mail message did not contradict either his sworn testimony or the department’s past statements. Brian Roehrkasse, a spokesman for the department, said: “We have consistently stated that, with the exception of Griffin, individuals were not pre-selected for any of the eight U.S. attorney positions prior to asking the U. S. attorneys to resign. The list made public today had previously been shared privately with Congress, and it in no way contradicts the department’s prior statement. The list, drafted 10 months before the December resignations, reflects Kyle Sampson’s initial thoughts, not pre-selected candidates by the administration.”

Mr. Sampson’s lawyer, Bradford Berenson, also denied that the message contradicted Mr. Sampson’s testimony. “Kyle’s testimony regarding the consideration of replacements was entirely accurate,” Mr. Berenson said. “In December 2006, when the seven U.S. attorneys were asked to step down, no specific candidate had been selected to replace any of them, and Kyle had none in mind. Some names had been tentatively suggested for discussion much earlier in the process, but by the time the decision to ask for the resignations was made none had been chosen to serve as a replacement.”

The possible replacements selected by Mr. Sampson — with the exception of Mr. Griffin — never materialized, at least in part because the controversy regarding the ousters has pushed aside consideration of who will fill the vacancies. But it is clear from actions taken over the last two years that Justice officials had placed lawyers from department headquarters, who were known to be loyal to Mr. Gonzales and President Bush, into open posts.