By the beginning of 1998, Brett M. Kavanaugh seemed set: a Yale law degree, three judicial clerkships, including one with Justice Anthony M. Kennedy, and, less than a decade out of law school, a coveted partnership at Kirkland & Ellis, a prominent law firm with offices a block from the White House.
At just 32, Mr. Kavanaugh had wrapped up a three-year stint working for his mentor, Ken Starr, on the sprawling Whitewater investigation of President Bill Clinton. The inquiry was finally winding down, and Mr. Kavanaugh believed it was in some ways deeply flawed, telling an audience at Georgetown University Law Center, “It makes no sense at all to have an independent counsel looking at the conduct of the president.”
Then, just as he was starting at the law firm, he went back.
For nearly seven months, Mr. Kavanaugh, now President Trump’s nominee to replace Justice Kennedy on the Supreme Court, worked for Mr. Starr once again, despite his objections, helping to assemble the case that the president had an affair with Monica Lewinsky and obstructed justice by trying to cover it up. It was Mr. Kavanaugh who pressed Mr. Starr to aggressively question Mr. Clinton on the details of his sexual relationship with Ms. Lewinsky and who drafted the section of Mr. Starr’s report to the House that laid out 11 possible grounds for Mr. Clinton’s impeachment.
Mr. Kavanaugh’s decision to return to Mr. Starr’s side plunged him into an immersion course in the brutal ways of Washington combat, forever connecting him to an investigation that Democrats called a partisan witch hunt, foreshadowing the epithet that Republicans now use to describe the efforts of the special counsel, Robert S. Mueller III.
Mr. Kavanaugh still regards Mr. Starr as an “American hero.” But whether as a result of mature reflection or the expedient recognition that he should distance himself from the politically radioactive prosecution, Mr. Kavanaugh now argues more forcefully against criminal investigations of sitting presidents.
“Like many Americans at that time, I believed that the president should be required to shoulder the same obligations that we all carry,” he wrote in a 2009 law review article, about 10 years after the Starr investigations ended.
“But in retrospect,” he said, “that seems a mistake.”
That position has an obvious appeal to the White House and allies of Mr. Trump. But to Democrats who objected to Mr. Starr’s investigation and are now the ones looking to a special counsel to find criminal activity in a president’s activities, there is more than a little irony in Mr. Kavanaugh’s shifting positions.
“It redefines flexibility,” said Rahm Emanuel, the mayor of Chicago, who was a senior adviser to Mr. Clinton at the time.
A Different Kind of Investigation
Mr. Starr’s investigation at first focused on the Clintons’ involvement in an Arkansas real estate deal and grew to consider other matters: the death of Vince Foster, a White House lawyer; the firings of employees of the White House travel office; and various inquiries into possible obstruction of justice.
Mr. Kavanaugh, for his part, prepared a report concluding that Mr. Foster had committed suicide, investigated whether documents had been unlawfully removed from Mr. Foster’s office, and litigated cases on attorney-client and executive privilege.
When he returned to the independent counsel’s fourth-floor offices at 1001 Pennsylvania Avenue, just across the street from the F.B.I. headquarters, it was to a far different investigation.
News of the Lewinsky affair broke in January 1998, after Mr. Clinton testified in a sexual harassment suit that had been nurtured for years by a network of conservative lawyers. Paula Jones, an Arkansas state worker, said Mr. Clinton had made lewd advances in a hotel room when he was governor. In his deposition for the case, Mr. Clinton was provided a tortured definition of sexual relations — and denied engaging in such actions with Ms. Lewinsky.
Mr. Starr obtained permission from Janet Reno, the attorney general, and a three-judge panel to expand his investigation to include Ms. Lewinsky, and suddenly Mr. Kavanaugh’s former colleagues were under siege. An investigation that had begun by examining a complex real estate deal in Arkansas had become a tawdry exposé of the president’s sex life, complete with a semen-stained dress and a sex toy in the Oval Office.
“The moment they go into a different chapter, it becomes the most unprofessional investigation ever done,” Mr. Emanuel said. “They were not doing their job. They were leaking constantly, and they were trying to battle a presidency.”
Some members of Mr. Starr’s team, like Rod J. Rosenstein, now the deputy attorney general, and Alex M. Azar II, the current secretary of health and human services, were heading for the exits or keeping their distance. Neither returned to the Starr team after the Lewinsky scandal emerged.
But Mr. Kavanaugh was a Starr protégé — he started his legal career with a one-year fellowship in the office of the United States solicitor general when Mr. Starr held that office. And so when his old boss called on him in April 1998, Mr. Kavanaugh did not say no right away. His partners at Kirkland & Ellis thought he was crazy for even thinking about going back. In the end, loyalty prevailed.
“We begged and begged and begged,” said Robert Bittman, the deputy counsel who led the Lewinsky prosecution for Mr. Starr. “He really liked big legal issues. That was my pitch to him. Eventually, he succumbed and came back.”
At the Georgetown Law Center event earlier that year, a moderator had asked the panel that Mr. Kavanaugh was on: “How many of you believe as a matter of law that a sitting president cannot be indicted during the term of office?” Mr. Kavanaugh raised his hand.
Still, he reasoned, impeachment was another matter. It was one thing to have concerns about an unrestrained prosecutor. But the Constitution made it clear that Congress should have the power to address presidential misdeeds, so when he returned to the Starr investigation, Mr. Kavanaugh gave no indication that he had any doubts about laying the groundwork for Congress to remove the president.
That spring, Mr. Kavanaugh again became one of Mr. Starr’s top legal strategists in what became a fierce war with Mr. Clinton’s lawyers that involved strategic leaks to the press about evidence and, critics said, grand jury testimony.
Mr. Kavanaugh’s associates said they did not believe he was ever guilty of the kinds of leaks that Mr. Clinton’s lawyers repeatedly complained about. In a questionnaire that he submitted to the Senate last month, Mr. Kavanaugh wrote, without elaborating, that “I have also spoken to reporters on background as appropriate or as directed.”
Mr. Kavanaugh attended occasional dinners at Mr. Starr’s house, including one where the Capitol Steps, a musical satire group, performed. But he was not part of the poker games that a few of the lawyers sometimes held, one colleague recalled. Most described him as a quiet force at Mr. Starr’s daily 5 p.m. all-hands strategy sessions, speaking up only occasionally to help guide the legal debate.
“He’s always been a guy who is judicious in his comments,” said Sol Wisenberg, one of Mr. Kavanaugh’s colleagues at the time. “He’s not a shouter.”
In an office that included Democrats and Republicans, Mr. Kavanaugh was not openly ideological, according to several of the people who worked with him. But like the other lawyers, Mr. Kavanaugh was deeply invested in winning, and convinced of the president’s moral and criminal guilt.
“Were there people who disliked the president? Absolutely,” said Andy Leipold, a member of the Starr legal team who is now a law professor at the University of Illinois. “The more the attacks came — what we perceived to be unfair attacks — it was human nature. This guy just is not acting presidential.”
By the summer, the investigation that Mr. Kavanaugh had rejoined was seen by many in Washington as an out-of-control, puritanical crusade that had morphed into an unfair attempt to criminalize the president’s personal behavior — a perception that opinion polls showed was largely shared by the American people.
One of Mr. Kavanaugh’s former law partners urged him to leave before his career suffered permanent damage. Mr. Kavanaugh listened — and decided to stay.
“Brett’s recognition was that I needed all the help I could get,” Mr. Starr recalled. “By that time, Brett and I were very close. I think he responded to a friend in need.”
‘The President Has Disgraced His Office’
Mr. Starr and his lawyers grew obsessed with the president’s lies even as Mr. Clinton’s allies condemned the investigators as part of a right-wing legal conspiracy that had maneuvered to take him down.
The atmosphere inside the independent counsel’s office grew even more intense as it became clear that Mr. Clinton would testify in the Lewinsky case, and that Mr. Starr was determined to send an impeachment report to Congress.
As prosecutors prepared for their face-off with Mr. Clinton in August, Mr. Kavanaugh took a hard line in urging relentless and detailed questioning of the president, according to two people in Mr. Starr’s office who recalled a memo Mr. Kavanaugh sent urging the use of explicit questions during the interview.
“The president has disgraced his office, the legal system and the American people by having sex with a 22-year-old intern and turning her life into a shambles — callous and disgusting behavior that has somehow gotten lost in the shuffle,” Mr. Kavanaugh wrote in the memo, according to a 2010 book, “The Death of American Virtue: Clinton vs. Starr.”
In the memo, Mr. Kavanaugh added that Mr. Clinton had attacked the Starr team “with a sustained propaganda campaign that would make Nixon blush.”
Unless Mr. Clinton resigned or admitted to perjury and publicly apologized to Mr. Starr, Mr. Kavanaugh wrote, he should be asked detailed questions based on Ms. Lewinsky’s testimony about oral sex, masturbation and the like.
“If Monica Lewinsky says that you ejaculated into her mouth on two occasions in the Oval Office area, would she be lying?” was one of the questions Mr. Kavanaugh suggested.
Mr. Bittman said the memo was a misstep.
“Brett immediately regretted the tone of that memo,” he said. “My memory is that he was sleep deprived and then quickly realized in retrospect that it was over the top.”
As Mr. Starr’s self-imposed September deadline to deliver a report to Congress loomed, Mr. Kavanaugh focused on developing the grounds for Mr. Clinton’s impeachment, including sweeping charges of lying and obstruction of justice.
“He was a working machine,” Mr. Leipold recalled. “What I remember is him sitting at the computer with weeks, days, hours to go before the referral needs to go to the printer, working away, focused like a laser.”
But when the time came to provide Congress with a report, Mr. Kavanaugh grew distressed. In addition to outlining the possible case for impeachment, Mr. Starr also planned to give lawmakers an extended “narrative,” full of sordid details, about the affair between Mr. Clinton and Ms. Lewinsky.
“Brett was an advocate against explicit detail,” said Paul Rosenzweig, who took the opposite position during the heated strategy sessions on the issue. Mr. Rosenzweig and others, including Mr. Starr, thought they needed to include the details to prove their case that Mr. Clinton had lied.
Mr. Kavanaugh thought the sexual narrative would undermine the credibility of the office, and he predicted that it would be immediately leaked to the press by members of Congress. He urged Mr. Starr to at least write a blunt letter urging them not to make that part of the report public.
He lost both fights. The final report included all the sexual details, and quickly went online. In a 1999 interview with CNN, Mr. Kavanaugh said that decision had hurt Mr. Starr’s team.
“It really was a mistake for Congress to take this sensitive information, to put it on the internet before they even read it,” Mr. Starr said. “They had not even read the report, and obviously, given the nature of the case, there were going to be some sensitive details. I think that was a mistake, that was unfortunate, it redounded to our detriment.”
One of Mr. Kavanaugh’s last tasks in the investigation was to help prepare Mr. Starr for an appearance before the House Judiciary Committee in November 1998, including a two-hour statement that was considerably more sober than the report.
A week later, Diane Sawyer interviewed Mr. Starr and members of his team. She pressed them on how they had weathered the attacks by critics, many of whom challenged their legal integrity and their personal ethics.
“What happens when you meet people, and they say, ‘Where do you work?’” she asked Mr. Kavanaugh.
“It depends,” he replied, “who the person is.”
‘A Jurist or a Partisan?’
Not long after Mr. Starr’s high-profile testimony, the House voted almost entirely along party lines to impeach Mr. Clinton on two counts that mirrored parts of the grounds proposed by Mr. Starr and his protégé, Mr. Kavanaugh. But after a five-week trial in the Senate, Mr. Clinton was acquitted, with Republicans joining Democrats in opposing conviction.
It was a rough time for Mr. Starr’s team, which was roundly criticized in legal circles for having conducted an obsessive inquiry into unseemly but private conduct.
“This was a crusade to find some way to get Bill Clinton, and maybe Hillary, too,” said Stephen A. Saltzburg, a law professor at George Washington University.
But it was also an energizing period for America’s conservative movement — a time when a sprawling network of Federalist Society lawyers, Republican lawmakers and Washington lobbyists came close to taking down a sitting Democratic president. The clash with the Clintons over Ms. Lewinsky cemented the right’s hatred of the president’s family, accelerating a partisan divide in Washington that has gripped the city ever since.
“The mania of hunting Clinton was certainly a phenomenon in the larger conservative movement,” said Steven Teles, the author of “The Rise of the Conservative Legal Movement.” But he said the inquiry was less central in the legal history of that movement because “there was a slight embarrassment at the Starr investigation among legal conservatives.”
The investigation was nonetheless a training ground for talented conservative lawyers, said Rory Little, a law professor at the University of California’s Hastings College of the Law.
“The partisan nature of the inquiry attracted people with a partisan view,” he said. “And you knew you were going to be well connected on the Republican side of the political aisle afterward.”
That was the case for Mr. Kavanaugh. The four years he spent on the Starr investigation cemented his conservative credentials and set in motion a legal career that included five years working for President George W. Bush, first in the White House Counsel’s Office and then as Mr. Bush’s staff secretary. Ultimately, Mr. Bush appointed him to the United States Court of Appeals for the District of Columbia Circuit.
It took two tries. His first nomination, in 2003, stalled after Senate Democrats questioned his role in preparing what Senator Chuck Schumer, Democrat of New York, called “the notorious Starr report.” Mr. Kavanaugh was finally confirmed in 2006.
Over time, Mr. Kavanaugh has said, his doubts about the Starr inquiry grew. After eagerly participating in the vilification of a Democratic president, Mr. Kavanaugh has come to view such investigations with suspicion.
In 2006, he said it was a mistake to have expanded the scope of Mr. Starr’s jurisdiction to include the Lewinsky affair, saying that “it created the impression that Judge Starr was somehow the permanent special investigator of the administration.”
And by 2009, after working for Mr. Bush, Mr. Kavanaugh developed a new appreciation for the burdens of the presidency. He said in a law review article that the nation “would have been better off if President Clinton could have focused on Osama bin Laden without being distracted by the Paula Jones sexual harassment case and its criminal investigation offshoots.”
Though his evolution began years ago, at the beginning of the Obama presidency, some find it convenient that he now opposes any criminal investigation of a president just as a Republican is a target. That is sure to be at the center of the grilling he faces during his confirmation hearings. Democratic senators will want to know how he will approach disputes arising from the investigation of Mr. Trump.
“The question is: Are we going to get a jurist or a partisan?” Mr. Emanuel said. “I think that’s a fair question. They are going to have to look at the entirety of his work and make a judgment. It’s part of his life’s work.”