That turned out to be a job that extended over four decades, because as bright and kind and wise as friends say Kavanaugh is, he has also left behind a trail of people who say that his reckless behavior raises serious questions about his judgment and veracity.
The story of President Trump’s embattled choice for the Supreme Court is a classic Washington tale of a young man who grew up surrounded by people in high places, keenly aware of protecting his image. He told a friend in college that he didn’t plan to buy stocks as an adult because he had to avoid conflicts if he wanted to follow in his mother’s footsteps as a judge.
Kavanaugh’s story is also one of the power and insularity of wealth. He grew up in an idyll of country clubs and beach retreats, private schools and public prominence. The only child of a lobbyist and a judge, he had parents who pushed him hard, teachers who assured him that he faced no limits, and friends whose families knew the art of making problems go away quietly.
That Kavanaugh would achieve greatness seemed certain. Some of his classmates called him “The Genius.” They liked him because he was smart and fun. Women found him thoughtful and empathetic. Men said he was a guy’s guy — a walking encyclopedia of sports, a good pal, always up for a beer.
But again and again as he rose to the pinnacle of official Washington, Kavanaugh has given those charged with examining his life and character reason to pause and dig deeper.
This time, as he faces the Senate vote that will determine whether he will spend the rest of his working life at the apex of American democracy or in permanent disgrace, he is up against devastating allegations that he was a nasty, belligerent drinker who, according to his chief accuser, Christine Blasey Ford, pinned her to a bed and held his hand over her mouth when she tried to stop his sexual assault when they were in high school.
Once again, schoolmates, friends, family members and co-workers have rushed to his defense.
“After law school, Brett started on a path of high-profile jobs, and we were rooting for him all along,” said Tom Kane, a Georgetown Prep classmate and friend. “Between 1998 and 2004, I lost my father, my mother and my sister, and he was always there for me. He has a fricking conscience and a soul unlike what people say.”
This story about Kavanaugh’s rise — and how his upbringing amid Washington’s political and social elite has helped protect him from his missteps — is based on dozens of interviews with friends, classmates, co-workers and mentors, including some who think he has been grievously wronged in the confirmation process and others who think he is unfit to serve.
When the American Bar Association first considered Kavanaugh’s nomination to a judgeship, the committee assigned to check him out ended up talking to more than twice as many lawyers and judges as many investigations required.
Some of those who spoke to the ABA in 2006 raised concerns about Kavanaugh’s lack of experience. Some warned about his temperament. He “dissembled,” one lawyer said. He was described as “insulated,” “immovable,” “very stubborn and frustrating to deal with.”
Kavanaugh pushed back, bolstered by his tight network. Supporters were always offering his name when sterling positions opened up, singing his praises to those making decisions about clerkships, law firm jobs, White House appointments and judgeships.
When it came time for Kavanaugh to marry after years of playing the field, it was the president of the United States who encouraged him to do so. Kavanaugh, like fellow Yale alumnus George W. Bush, settled down with a strong woman from a modest West Texas background. Bush, who held a sit-down dinner for the couple in the Rose Garden, called their marriage “the first lifetime appointment I arranged for Brett.”
Fourteen years later, Bush would get on the phone to rally senators to try to save Kavanaugh’s troubled nomination.
Now, as Kavanaugh’s suitability to serve on the nation’s highest court is considered by the Senate, and especially by three Republicans who delayed jumping on board their party’s express train to confirmation, the judge faces the most severe test of what looks to outsiders like a charmed life.
This moment — an excruciating mix of careful inquiry into his legal opinions and voracious inspection of his adolescent behavior, all taking place amid a searing national struggle involving truth, trust, political polarization and sexual mores — has left Kavanaugh’s community deeply, perhaps irrevocably, divided.
Some have fixed on hazy but painful recollections of ugly nights in the 1980s — a bar fight, groping attempts to get somewhere with women, perhaps worse. Others slot those same stories into memories of a debauched but too-common scene of cloistered young men learning how far was too far, even as they prepared to run the world.
No one who hung out with Kavanaugh during Beach Week on the Maryland shore or at Demery’s bar in New Haven, Conn., knew their partying would become the stuff of congressional debates and national polls, or that the president would conclude that their friend “did have difficulty as a young man with drink.”
Any definitive version of what happened between Kavanaugh and Ford 36 years ago seems lost to history.
More than most people, by virtue of where and how he grew up, Kavanaugh knew he would someday be called to account for himself. He did not, however, expect to be asked to answer for the ways and mores of the place and time that shaped him, as he has described the current inquiry to friends. Yet here he is, in a humiliatingly intimate and public job interview that has turned into a historic reckoning, for Kavanaugh and for his country.
'We had something to prove'
There are so many automatic advantages that come from attending the 229-year-old Georgetown Preparatory School, set back from busy Rockville Pike in North Bethesda, Md., on a verdant campus larger and more stately than those of most universities.
There is the intimacy of small classes and the lesson drummed in by Jesuits at the Catholic school that the boys are expected to excel and to serve. There is the continuing pride in single-sex education, the unfashionable idea that wisdom and power are unlocked by channeling adolescent energy into studies.
The boys, in the 1980s perhaps even more than in decades before and after, believed that their hard work bought them enough slack that they could get away with hard partying.
“We did everything to the max,” said one of Kavanaugh’s classmates, who, like many of his peers, spoke on the condition of anonymity because, as he put it, “Brett doesn’t want us putting ourselves out there right now.”
Many of the boys at Prep came from families accustomed to gaining and holding influence. Kavanaugh’s father, Edward Kavanaugh, was president of what was then the Cosmetic, Toiletry and Fragrance Association, the kind of Washington job in which building connections to powerful people justified the $4.57 million in compensation he earned in 2005, according to tax returns. His mother, Martha Kavanaugh, was a prosecutor who became a circuit judge in Montgomery County.
Perhaps the greatest privilege the boys gained at Prep was one another. Some graduates came to view the school as a troubled, morally questionable symbol of a snobby elite; others cherish the place as a foundry for men of character and achievement. But most bonded over the idea that they were the elect who owed one another a permanent duty.
Many also shared a sense that they were looked down upon. Even as much of the outside world viewed them as part of a narcissistic elite, they grew up hearing that theirs was a lesser private school, academically no match against St. Albans, Sidwell Friends or St. Anselm’s.
“We had something to prove,” one of Kavanaugh’s classmates said. “We were supposedly the dumb jocks, the party guys.”
Since graduation, the men of the Class of 1983 have supported those among them who have faced difficulties. They took classmate Mark Judge to his cancer treatments and helped him when he had other problems, several classmates said. They assisted another classmate who fell behind with mortgage payments.
Since Kavanaugh was nominated, members of the class — some from his inner circle, some who’d never been close — have created a support network that has fended off reporters, offered guidance to favored journalists and batted down false rumors, all with frequent consultation with their former schoolmate.
They had done this before. Judge, a good friend of Kavanaugh’s in high school, became a freelance writer and in his books, which include two memoirs, he described an alcohol-saturated adolescence. A central character in Judge’s account was named “Bart O’Kavanaugh.” Kavanaugh was nicknamed Bart in high school.
Years before his Supreme Court nomination, Kavanaugh’s supporters pressed Judge to limit or mask his revelations of bad behavior, three Prep classmates said.
At Prep, as at almost every stage of his life, the impressions people formed of Kavanaugh were consistently inconsistent.
Kavanaugh and other football players were at the center of Prep’s social universe. Matt Brown, a classmate who was decidedly not part of the in crowd, remembered Kavanaugh standing out among the popular boys because he was so nice.
Many football players let their gridiron celebrity “get to their heads and they wouldn’t really interact with you,” said Brown, now an alcohol and drug counselor in Portland, Maine. Not Kavanaugh: “He was a guy who would still talk to you in the hallways and would acknowledge your existence.”
Classmate William Fishburne recalled Kavanaugh as an academic standout, a popular jock. But he also recalled a different side of Kavanaugh.
Fishburne was short and heard more than his share of short jokes on campus. He was also a star in high school debate, and he said Kavanaugh “liked to call me a master debater,” but he’d say it in such a way that others heard “masturbator” — the kind of schoolyard teasing that brought easy laughs, but also humiliated the recipient.
“The whole group there did not treat me well,” Fishburne said. “Brett was a jerk.”
A consistent conservative
At Yale College and Yale Law School, as at Prep, there are classmates who say Kavanaugh was a big drinker who became nasty and belligerent when he got drunk and classmates who say he drank heavily but never seemed out of control.
The two portraits seem irreconcilable, yet both could be true.
“Brett was a sloppy drunk, and I know because I drank with him,” said Elizabeth M. Swisher, a friend who is now a professor of gynecologic oncology at the University of Washington School of Medicine. “He’d end up slurring his words, stumbling. . . . It’s not credible for him to say that he has had no memory lapses in the nights that he drank to excess.”
But Chris Dudley, a close friend who played basketball at Yale and later in the National Basketball Association, painted an opposite picture. “I went out with him all the time. He never blacked out,” Dudley said. “Brett drank and I drank. Did he get inebriated sometimes? Yes. Did I? Yes. Just like every other college kid in America.”
Just as there are women who say Kavanaugh was clumsy or rough when he made drunken passes at them, there are women who say he was charmingly awkward and reticent in such moments.
Even as classmates remain divided over his behavior when drinking, they agree that he was a consistent conservative on a liberal campus.
As a first-year law student in 1987, Kavanaugh aligned himself with Chief Justice William H. Rehnquist, a conservative who moved the Supreme Court to the right.
“In class after class, I stood with Rehnquist. That often meant . . . that I stood alone,” Kavanaugh said in a speech last year. “Some things don’t change.”
Kavanaugh soon joined the Federalist Society, a Washington-based group that has played a key role in recruiting, grooming and supporting strongly conservative judges — including Kavanaugh.
In the years to come, he would appear nearly 50 times before Federalist Society audiences on campuses and at gatherings of lawyers, according to data he gave the Judiciary Committee.
As Kavanaugh became active in the society’s Yale chapter, Leonard Leo got involved with the group at Cornell. The two soon formed a bond that would prove powerfully important. Both men were originalists, subscribers to the idea that the Constitution and statutes should be interpreted by their original meaning and text.
In Washington, Leo, who emerged as a leader of the Federalist Society, became the keeper of a list of influential conservative judges from which Republican presidents have chosen court nominees. Leo was also, as ever, one of Kavanaugh’s most avid boosters.
A Starr protege
After law school, Kavanaugh clerked for two federal judges, lining himself up for a coveted clerkship at the Supreme Court. But before Justice Anthony M. Kennedy hired him, Kavanaugh caught the eye of another prominent conservative who would prove to be a vital mentor.
Like Kavanaugh, Kenneth W. Starr was a staunch conservative who would be accused of excessive partisanship in a job that required a fair and neutral temperament. But what drew Starr, an independent counsel appointed to investigate allegations against President Bill Clinton in 1994, to hire Kavanaugh three times was the same mix of attributes that had attracted so many people before him: He considered the young lawyer an unusually likable guy who was brilliant and closely aligned with Starr’s philosophy.
In 1992, when Starr was U.S. solicitor general, the federal government’s lawyer in the Supreme Court, he interviewed Kavanaugh and hired him as a fellow in his office. From there, Starr lent a hand as Kavanaugh sought the Kennedy clerkship.
Starr kept a close eye on his protege and a few years later recruited him to join the independent counsel’s office, first to investigate the death of White House deputy counsel Vincent Foster and later, after Kavanaugh had left the office, to come back and lay out the reasons the president should be impeached for lying about his affair with White House intern Monica S. Lewinsky.
As Starr and his deputies discussed how to handle the questioning of the president, some wondered whether Clinton should be cut some slack out of respect for his office.
On the night of Aug. 15, 1998, Kavanaugh answered with an impassioned memo: “I am strongly opposed to giving the President any ‘break’ in the questioning. . . . 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.”
Kavanaugh offered 10 questions to ask the president, including: “If Monica Lewinsky says that you inserted a cigar into her vagina while you were in the Oval Office area, would she be lying?”
The next morning, said Robert J. Bittman, then Starr’s deputy, Kavanaugh expressed remorse about some of the tone of his assessment of Clinton, but not about the questions.
Kavanaugh’s next assignment was to write a section of the report to Congress laying out the grounds for impeaching the president.
“This was not a man on a mission, this was a legal document of great potential moment that needed to be very carefully crafted, so I was looking to one of the office’s most talented lawyers,” Starr said in an interview last summer.
The bond between Kavanaugh and Starr was mutual. Starr had been bitter about being passed over by President George H.W. Bush for a Supreme Court nomination, but when he heard that Trump had nominated his protege for the high court, Starr said it brought “tears to my eyes. Tears of joy.”
A network of supporters
Kavanaugh’s rise was swift and deliberate. At every step, his friends pitched in. Starr, Leo and others recommended him, spread the word, helped knock down critics.
In 2003, Kavanaugh’s name was advanced to the White House for nomination as a judge on the U.S. Court of Appeals for the D.C. Circuit.
“I thought — correctly! — that Brett would make a great judge, given his A+ level smarts, collegial demeanor, commitment to public service, compassion,” Kyle Sampson said in an email. He was chief of staff to Alberto R. Gonzales, who was attorney general by the time Kavanaugh was confirmed to the position in 2006.
The chain of connections was echt-Washington: Kavanaugh and Sampson had worked together on the nomination of another judge, John Bates, and Kavanaugh and Bates had worked together in the independent counsel’s office.
“I went and made the case to Judge Gonzales,” Sampson said, “and then Gonzales made the case to President Bush and he agreed.”
When the American Bar Association knocked down its rating of Kavanaugh from “well qualified” to merely “qualified,” and Democrats blocked his nomination to the D.C. Circuit, his friends rallied once more. More than two years after he was first chosen, he won a spot on the bench by a nearly party-line vote in the Senate.
On the bench, Kavanaugh extended his network. Other judges began to cite his rulings frequently. He is among the top appellate judges nationally to send his law clerks on to clerkships in the chambers of Supreme Court justices.
At Harvard Law School, where Kavanaugh taught for a decade before this week’s announcement that his class has been canceled, he invited students to dinners and encouraged them to stay in touch. Colleen Roh Sinzdak, a 2010 graduate, said Kavanaugh helped her get a Supreme Court clerkship even though she has been a lifelong Democrat.
After the court upheld Trump’s travel ban earlier this year, Sinzdak felt crushed. She was surprised that night to receive a sympathetic email from Kavanaugh, who probably disagreed with her on the issue, encouraging her to keep her chin up. “That meant a lot,” she said.
'A tough process'
Last week, on the day before the Senate Judiciary Committee hearing about the allegations against him, Kavanaugh spent hours behind closed doors in his courthouse office, writing an angry, emotional defense of who he is. He struggled to deliver the speech even in practice runs, according to a person familiar with the sessions.
His opening remarks were searing, partisan and accusatory; his delivery, by turns outraged, weepy and righteous.
When Sen. Amy Klobuchar (D-Minn.) questioned Kavanaugh, the judge initially came across as courteous and diplomatic. But when she asked whether he had ever blacked out after a night of heavy drinking, Kavanaugh pounced with his own question.
“I don’t know,” he snapped. “Have you?”
During breaks in his testimony, Kavanaugh regularly huddled with White House counsel Donald McGahn and other advisers in a small meeting space behind the hearing room.
But after the heated exchange with Klobuchar, Kavanaugh took a moment to reflect. His family and friends were out there in the hearing room. With everything on the line, he had to make his own way.
Just before the hearing resumed, he told his advisers that he wanted to apologize to the senator, said a person familiar with the discussion.
“Sorry I did that,” he told Klobuchar when the hearing resumed. “This is a tough process.”
That night, Kavanaugh, emotionally spent, his future very much up in the air, retreated to safe ground. He spent the evening with those who would understand, the ones who had been there at every step, including, of course, his buddies from Prep.
Correction: An earlier version of this story incorrectly said Alberto R. Gonzales was attorney general in 2003. This story has been updated.
Amy Brittain, Emma Brown, Alice Crites, Amy Gardner, Shane Harris, Joe Heim, Michael E. Miller, Robert O’Harrow, Susan Svrluga, Julie Tate and Dan Zak contributed to this report.