Trump’s Choice? Beltway Insider Born and Bred

When Judge Brett Kavanaugh introduced himself to the American people Monday, with a beaming President Donald Trump beside him, he had a lot to say about his mother, a former high school teacher and a Maryland judge. He accorded his father strikingly less attention — just 34 words, compared with 132 about his mother — mentioning his “unparalleled work ethic” while not saying exactly what work he did.

Yet Ed Kavanaugh’s career may shed light on his son’s hostility to government regulation, a major reason conservatives are so enthralled by his son’s nomination to the Supreme Court. He spent more than two decades in Washington as a top lobbyist for the cosmetics industry, courting Congress and combating regulations from the Food and Drug Administration and other agencies. (Among his hires for legal work: John Roberts, now the chief justice.)

In current parlance, as an old friend put it, the elder Kavanaugh and his associates were “swamp creatures,” using money and connections to fend off demands for safer products and greater transparency about ingredients. He was a golf partner of former Rep. Tip O’Neill, D-Mass., the longtime House speaker, who weighed in to support Martha Kavanaugh’s nomination to a judgeship. He was paid $13 million, including his retirement package, in 2005, his last year at the Cosmetics, Toiletry and Fragrance Association, records show.

Now Brett Kavanaugh, should he be confirmed, will cement a solid pro-business majority on the nation’s highest court, advancing Trump’s aim of dismantling the regulatory state, liberating industry from what he sees as burdensome rules. With critical battles over the environment and consumer protection headed for the courts, his ascent would likely achieve for industry incomparably more than all his father’s years of lobbying.

That is clearly the White House’s hope: An official fact sheet declares that “Judge Kavanaugh protects American businesses from illegal job-killing regulations” and — in an unusual claim about a judge — “has led the effort to rein in unaccountable independent agencies.” It is also one reason his confirmation is opposed by many advocates for consumers, environmental protection and workers.

But as with any nominee, Kavanaugh and his supporters are carefully shaping his narrative for the diverse Senate and the broader American public: his mother the judge, not his father the lobbyist; his parents’ early struggles, not their second homes in the Florida Keys and on Maryland’s Eastern Shore; his service as a children’s sports coach and a Catholic volunteer, not his participation in some of the most bitter partisan fights in recent times.

They do not let on that Kavanaugh is by legacy and experience a charter member of elite Washington: His family’s government-centric social circle, his two summer jobs on Capitol Hill, his White House service, his golfing at the capital’s country clubs, his residence in one of the richest suburban enclaves in the United States. Nor do they note that Kavanaugh’s nomination is the culmination of a 30-year conservative movement to shift the judiciary to the right.

In retrospect, his climb to a justice’s seat may seem calculated — from pursuing jobs that put him close to the nation’s most powerful men to the moment he raised some eyebrows by praising Trump for the breadth of his candidate search (“No president has ever consulted more widely ... ”). Although the president talked with many people about his choices, he selected Kavanaugh from a list compiled with the guidance of conservative activists.

Yet by many accounts, the conservative combatant of the Bill Clinton investigation and the 2000 Florida recount who has spent a dozen years as an appellate judge is also a generous friend, including to many Democrats; an authentic sports fanatic who keeps a beat-up basketball in his chambers; and a warmhearted family man.

This examination of Kavanaugh’s personal life and career is drawn from interviews with more than 60 people who know him and a review of his judicial opinions, speeches and other public records. Law clerks recall his carrying a tattered index card in his shirt pocket with life maxims like those he urged in a speech to Catholic University law graduates in May: “Love your friends, live on the sunrise side of the mountain and stay humble.” In the confirmation fight just getting underway, his opponents will discover plenty in his record not to like, but those who know him say they may find it a challenge to vilify him personally.

Greg Chernack, chairman of the town council in the Kavanaughs’ neighborhood outside Washington, said the Supreme Court nominee was a regular at community events, chatting about his love for the Washington Nationals and Bruce Springsteen.

Chernack, a lawyer, said he found Trump “reprehensible” and had concerns about the judiciary. Of Kavanaugh’s judicial philosophy, he said, “We disagree on things.”

Still, he said of Kavanaugh and his wife, Ashley, who is the town manager, “I think the world of both of them.”

He was an only child but had a pack of friends, who remember riding bikes, buying baseball cards and playing in Catholic youth basketball games. He attended all-male Catholic schools, winning the headmaster’s award in seventh grade and saving his parents a year’s tuition. During his junior high and high school summers, he had a one-man business cutting neighbors’ lawns.

Still, he was a son of privilege, at least by his teenage years, when his parents’ careers took off. His parents were featured in a 1985 Washington Post Magazine article about working with an interior designer to redecorate their brick Colonial, using tiles Ed Kavanaugh picked up in Portugal for a custom-made dining table and purchasing vases and a gilt wood carving from Hong Kong.

And the family was deeply tied to official Washington. “He’s a fellow child of a D.C. mover and shaker,” said Elvis Oxley, the son of former Rep. Michael Oxley, R-Ohio. Their families vacationed together, and Elvis Oxley later went to work for the same cosmetics lobby Ed Kavanaugh had.

Brett Kavanaugh, 53, has sometimes traced the roots of his conservative politics to his early teenage years, when he took an interest in his mother’s work as a local prosecutor at home and the Iran hostage crisis abroad. He liked what President Ronald Reagan said about national security, cementing his allegiance to the Republican Party at an early age. (His father is a registered Republican; his mother registered as a Democrat but later signed on as a Republican in Florida.) Friends say he has not fundamentally changed his views since then.

Inspired by some of his teachers, Kavanaugh briefly considered becoming a history teacher and coach when he finished a bachelor’s degree in history at Yale, where his grandfather had graduated in 1929. But as a teenager he had been captivated by his mother’s tales of bank robberies and police sleuthing, and for years Kavanaugh wanted to be a prosecutor too. So he went straight on to Yale Law School in 1987, sharing a New Haven, Connecticut, house with seven other students, most of them Democrats.

“The house was so nasty that all the college frats had turned it down as unsanitary,” he recalled in a commencement speech this year at Catholic University’s law school. The friends left their doors open and wandered in and out of one another’s rooms, and the house was known for its parties.

Despite the socializing, said Jim Brochin, one of the tight group of housemates and now a lawyer in New York, “You knew right away that he was a very industrious person and student.”

Kavanaugh’s talents did not always stand out at Yale, where his class was full of academic stars and would produce several federal judges. One of them, James Boasberg, now a U.S. District Court judge in Washington appointed by President Barack Obama, lived in the house and remains a close friend of Kavanaugh.

Even before Kavanaugh took a seat in George Priest’s classroom to study antitrust law, the two had gotten to know each other on Yale’s basketball courts, first playing in pickup games. Throughout Kavanaugh’s life, being “obsessed” with sports, a friend said, has helped him bond with others.

“I have played a lot of basketball with him,” said Priest, whose role in the younger man’s rise in conservative legal circles would prove crucial. “You learn a lot about the character of a person by playing basketball with him. He is an incredibly decent person.” Priest, a longtime sponsor of Yale’s chapter of the Federalist Society, described his former student as “slightly conservative,” but not an outspoken activist. In interviews, friends and classmates agreed with that characterization, saying they knew Kavanaugh leaned rightward but couldn’t recall his arguing his views or even sharing them much.

“We knew his politics were probably more conservative than the rest of the members of the group, but it was not a topic of frequent discussion,” Brochin said. “He was not strident in the views he held. It was clear that civility was important to him.”

Nonetheless, Kavanaugh’s minority status at liberal Yale affected him. In a talk last year to the American Enterprise Institute about William Rehnquist, the conservative chief justice during Kavanaugh’s law school years, he described himself at the time as a lonely crusader for the right.

“In class after class, I stood with Rehnquist,” Kavanaugh said. “That often meant, in the Yale Law School environment of the time, that I stood alone.”

He was more religious than a typical law school student of the era and he attended Mass on Sundays. “As long as I’ve known him, it has been a part of his life,” Brochin said.

In a testament to Kavanaugh’s devotion to friends, every year for 27 years the former housemates have gathered for reunions, going rafting or biking, taking in spring training or the World Series. Even as he has held a string of high-powered positions, Kavanaugh has changed very little, Brochin said. “He was always very ambitious, in a good way — he was very good at positioning himself at the right place and with the right people,” he said. “He is very much the same person.”

At Yale, Kavanaugh developed relationships with several prominent professors who had reputations for helping students win coveted judicial clerkships — visiting during office hours and asking for recommendations.

He interviewed for a clerkship with a liberal judge, but ultimately landed one with a conservative, Judge Walter Stapleton, a Delaware federal appeals court judge who was not considered a “feeder” — a judge whose clerks had a realistic shot at a prestigious Supreme Court clerkship.

He was working for Stapleton in spring 1991 when a major abortion rights case, Planned Parenthood v. Casey, came before his court. Stapleton wrote the majority opinion, which upheld many provisions of a strict Pennsylvania abortion law that a district court judge had struck down. (A representative of Kavanaugh’s confirmation team declined to comment on whether he had been involved in the opinion.)

The next year, he took the unusual step of accepting a second appeals court clerkship. Judge Alex Kozinski of the 9th Circuit, a conservative known as a difficult boss but whose chambers were a launching pad for a Supreme Court clerkship, had an opening for a clerk and turned to Priest, a friend, for suggestions.

“I called Kavanaugh and asked him, ‘Do you want to do another clerkship?'” Priest recalled. The match was made. “He thought Brett was just fantastic,” Priest said of Kozinski. Friends say the job marked Kavanaugh’s rise to legal stardom and honed his conservatism to focus on the exact words of the Constitution, which he would later call “a document of majestic specificity.” The clerkship wasn’t easy. “When we started as law clerks, he told us we work for the people and we should consider ourselves on the job 24 hours a day, seven days a week, 365 days a year,” Kavanaugh testified during his 2006 confirmation hearing. “And I can say from personal experience that Judge Kozinski lived up to that promise.”

(Kozinski retired last year after multiple women accused him of sexual harassment, and some opponents of Kavanaugh have questioned whether he knew or should have known about the abuse. A spokeswoman said he never heard any sexual harassment allegations against Kozinski until they surfaced publicly last year.)

Shooting for the highest rungs of the legal world, he applied to clerk for Rehnquist. He has told colleagues that he scored an interview, though he did not get the job. Kavanaugh went on to a fellowship in the solicitor general’s office, which argues for the government before the Supreme Court.

His work with Kozinski eventually paid off: He did get a Supreme Court clerkship. It was with Justice Anthony Kennedy, whose seat he has now been nominated to fill.

By the time Kavanaugh completed his clerkship, his glittering résumé and professional networking were opening doors. Ken Starr, his boss in the solicitor general’s office, recruited him to the law firm Kirkland & Ellis.

But before he could start a private-sector career, Starr recruited him for another role: in the independent counsel’s office, then gearing up to investigate the Clinton administration.

Starr assured Kavanaugh that the job would last six months, maybe a year, Starr recalled. In the end, Kavanaugh would serve two stints totaling about four years.

At first, Kavanaugh examined the suicide of Vincent Foster, the deputy White House counsel. Records from the National Archives show that Kavanaugh obtained receipts from the hotel that Foster visited days before his death and collected gruesome notes on the condition of his body.

Starr also assigned Kavanaugh to argue before the Supreme Court that Foster’s communications with his lawyers were no longer privileged because he was deceased. In what turned out to be his only appearance before the high court, Kavanaugh lost.

“I was sort of amazed that he was allowed to argue it,” said Craig Lerner, who worked in the independent counsel’s office and is now a professor at George Mason Law School, noting that Starr could have argued it himself. But, he added, “Brett was the leading member of the brain trust.” In an interview, Starr recalled that he “was very proud of him.”

Kavanaugh left the office in 1997 for Kirkland but hurried back the next year, after news broke about Clinton’s affair with a White House intern. Soon, he was helping draft the portion of the Starr report that identified potential grounds to impeach Clinton.

The report argued that the president could be impeached for lying to his staff and misleading the public — a theory that may prove damaging to Trump if applied to the current Russia investigation.

Kavanaugh failed to persuade Starr to remove the narrative portion of the report describing, in explicit detail, Clinton’s relationship with the intern, Monica Lewinsky, according to people involved in the process. In September 1998, when he heard that Congress was set to publicly release the report without having read it, Kavanaugh drafted a letter urging congressional leaders to think again. But Starr, who had already alerted lawmakers that his report contained sensitive material, declined to send the letter. Congress published the report.

Friends say Kavanaugh regretted the publication of the full report, which he felt led to a caricature of the independent counsel’s office reveling in the salacious details of a president’s sex life.

“I think when Brett says, ‘I wish we had done more,’ sure, we could have done more, but I thought we did a lot,” recalled Robert Bittman, who had been one of Starr’s top deputies. “We never thought Congress would abdicate their responsibility and release the report without reading it.”

That experience — and the upheaval Starr’s report caused at the White House — helped crystallize one of Kavanaugh’s most contentious viewpoints: Congress should protect sitting presidents from criminal prosecution so as not to distract them from the critical duties of their office. Kavanaugh’s misgivings about independent prosecutors, articulated in law review articles in 1998 and 2009, reflect a broader deference to presidential power that has infused his career ever since.

Senate Democrats have seized on the articles as potential red flags. Robert Mueller, the special counsel, has indicated he may subpoena Trump. If the issue were to end up before the Supreme Court, Kavanaugh could be the deciding vote. Despite his reservations about independent prosecutors, Kavanaugh has defended Starr in a series of op-ed articles, calling him “an American hero” and crediting him with uncovering “a massive effort by the president to lie under oath and obstruct justice.”

At a November 1999 “Kenneth Starr appreciation dinner” in Washington, Kavanaugh delivered a glowing speech in which he mused about Starr’s becoming an ambassador and hoped to one day “call him Mr. Justice Starr.”

The feeling is mutual: Starr has expressed enthusiasm for Kavanaugh’s nomination.

When President George W. Bush took office in 2001, his first White House counsel, Alberto Gonzales, hired Kavanaugh as an associate counsel in part because, in an applicant pool filled with well-credentialed Republican lawyers, his experience working for the Starr investigation gave him a niche — dealing with oversight and investigations — Gonzales recalled.

Kavanaugh advised the White House on dealing with the investigation into collapsed energy firm Enron. But much of his time went to judicial nominations, particularly to the D.C. Circuit on which he would later serve. He worked on the candidacy of Miguel Estrada, a prominent conservative who was blocked by Democrats, and he strongly backed nominating John Roberts, later to become chief justice.

The night of the Sept. 11 terrorist attacks, Kavanaugh and Brad Berenson, another former Kennedy clerk in the counsel’s office, worked till early morning in American University’s law library researching emergency powers statutes. Though he seems to have had little involvement in the Bush administration’s most controversial counterterrorism programs, his veracity about his involvement in detention policies would later be challenged.

At his 2006 judicial confirmation hearing, when asked about notorious legal memos allowing a variety of torture techniques, Kavanaugh testified that he had not known about them and had had no involvement in “questions about the rules governing detention of combatants.”

That statement came under scrutiny the next year, when The Washington Post reported an anecdote about a 2002 White House debate over whether to deny two U.S. citizens — terrorism suspects who were being held as wartime detainees — access to defense lawyers.

Because lawsuits challenging the suspects’ indefinite detention were likely to reach the Supreme Court, where Kennedy was a swing vote, Gonzales consulted both former Kennedy clerks on his staff. Berenson and Kavanaugh told him that Kennedy was likely to rule that citizens have a right to lawyers, so they advised that the administration grant that access rather than inviting defeat in the courts. Vice President Dick Cheney’s lawyer, David Addington, opposed that position. Democrats asked whether The Post’s account suggested that Kavanaugh — by then on the bench — had delivered misleading testimony. Sen. Patrick Leahy, D-Vt., who was then chairman of the Judiciary Committee, went so far as to make a criminal referral to the Justice Department, though nothing came of it.

Kavanaugh’s defenders portrayed that episode as an exception in which he was consulted because of his insights into Kennedy, saying he otherwise had no role in detainee policy. Potentially dovetailing with that account, as late as January 2003 Cheney — a chief architect of the administration’s post-9/11 national security policies — had apparently not even heard of him.

According to Gonzales’ 2016 memoir, when Kavanaugh conveyed to the White House Bush’s instructions on an affirmative action case, Cheney summoned Gonzales to his office and sternly asked, “Do you have a Brett Kavanaugh working for you?”

Kavanaugh, who during the Starr investigation had gone to a few parties with conservative pundit Laura Ingraham, had started dating Bush’s personal secretary, Ashley Estes. When the two married in 2004, the president and first lady attended the ceremony. By then, Kavanaugh had left the counsel’s office to become White House staff secretary, a role that controls the flow of papers into and out of the Oval Office.

Edward McNally, who worked on homeland security legal issues in the White House, said Kavanaugh had to ensure that every word of proposed executive orders or speeches was vetted by the relevant agencies before going to the president, sometimes trying to reconcile competing views. “He was regarded as a fair, neutral, straightforward arbiter,” McNally said.

It was a White House colleague, D. Kyle Sampson, who suggested he might make a good judge. After asking whether Kavanaugh was interested, Sampson told Gonzales, who told Bush, who nominated him to the U.S. Court of Appeals for the District of Columbia.

But he would stay at the White House for the next three years because Democrats, citing his partisan history, including his work on the Starr investigation, initially blocked his confirmation.

He makes $220,600 as a federal judge, and Ashley Kavanaugh earns about $60,000 as town manager. Given that pay and his parents’ wealth, the assets he reported last year were surprisingly modest: less than $65,000. (The number excludes the value of his house and retirement account.)

By 2006, the American Bar Association, sometimes accused by conservatives of leaning left, had downgraded its 2003 rating of Kavanaugh as “well qualified” to become a federal judge to merely “qualified.” One of the evaluators found him “sanctimonious” and another “stubborn and immovable.” Several found his experience scant, noting that he had “never tried a case to verdict or judgment.”

Those critiques proved no obstacle. After a bipartisan group of senators struck a deal to resolve Democrats’ filibustering of several of Bush’s judicial nominees, including Kavanaugh, the confirmation process finally moved forward. At the opening of Kavanaugh’s confirmation hearing, Sen. Orrin Hatch, R-Utah, noted the nominee’s status as the scion of his lobbyist father, who had retired a year before. “He is deservedly admired by many in this town,” Hatch said of Ed Kavanaugh.

Brett Kavanaugh was confirmed 57-36, with only four Democrats voting in his favor. In his dozen years on the D.C. appeals court, the balance has shifted: Republican appointees initially dominated, but since 2013 they have been outnumbered by Democratic appointees, and Kavanaugh has found himself dissenting more often.

His record in the Supreme Court has been exceptional, with the justices adopting positions advanced in his opinions 13 times.

Sometimes the Supreme Court sustained his views after hearing an appeal in a case in which he had written an opinion. At other times, it agreed with a position he had advanced, but in separate cases from other courts raising the same issue, often citing Kavanaugh’s earlier opinion.

His successes involved cases concerning environmental regulations, criminal procedure, the separation of powers and limits on suits against corporations accused of complicity in human rights abuses abroad. He took almost uniformly conservative positions. When a closely divided Supreme Court agreed with him, its conservatives tended to be in the majority. But the justices also favored his views in several cases by lopsided majorities or unanimously.

He was reversed just once, on an environmental case. Writing for a divided three-judge panel, he said the Environmental Protection Agency had exceeded its authority in how it held states responsible for air pollution that drifts across their borders and causes harm in downwind states. The Supreme Court ruled by a 6-2 vote that the agency’s approach was permissible.

Kavanaugh often expressed his views in an unusual format, dissenting from the full (or en banc) court’s decision not to rehear a case decided by a three-judge panel of which he had not been a member. Not all judges approve of such dissents, particularly when they are aimed at eliciting Supreme Court review.

“The judge steps out of the robe and into the role of an advocate, urging the Supreme Court to take the case,” Judge A. Raymond Randolph, one of Kavanagh’s current colleagues, wrote in 1992.

But Kavanaugh has used such dissents to press his views to several audiences: to the Supreme Court, which pays close attention to them when deciding whether to hear an appeal; to litigants, who have pursued legal strategies that Kavanaugh mapped out; and to the conservative legal movement, which got a detailed account of his views on legal issues not directly before him.

A dissent last year did all of those things. A three-judge panel had upheld the Obama administration’s “net neutrality” regulations, and the full D.C. Circuit declined to rehear the case.

Kavanaugh used the occasion to set out his views on two issues that are central to the conservative legal agenda: limiting the power of administrative agencies, and subjecting regulations involving speech to skeptical First Amendment scrutiny.

“The net neutrality rule is unlawful,” he wrote, “because the rule impermissibly infringes on the Internet service providers’ editorial discretion.”

In their appeals to the Supreme Court, which are pending, internet service providers and trade associations relied heavily on Kavanaugh’s dissent.

He has also been popular with the justices as a feeder judge, sending his law clerks to serve with Supreme Court justices across the ideological spectrum. A small number of feeders provide a large proportion of Supreme Court clerks, and the justices’ reliance on those judges is a mark of respect.

Kavanaugh’s main competitor as a feeder in recent years has been Judge Merrick Garland, whose nomination to the Supreme Court by Obama was blocked by Senate Republicans.

The White House first indicated in December that Trump would consider nominating Kavanaugh to the Supreme Court, when it issued a list of potential contenders if another vacancy arose. But in May 2016, when Don McGahn, then the top lawyer on the Trump campaign and now the White House counsel, put together the first list of potential Supreme Court picks to fill the vacancy left by the death of Justice Antonin Scalia, Kavanaugh was not on it.

Indeed, none of the 11 candidates on the first list were from inside the Beltway, underscoring Trump’s pledge to “drain the swamp” of the establishment.

If Kavanaugh was upset by the omission, he gave no public sign of it. Two weeks later, at a conference in early June 2016, he delivered a keynote speech on Scalia and judges’ deference to the administrative state.

“I loved the guy,” he said of the conservative icon. “To me he was and remains a hero and a role model.”

Kavanaugh praised Scalia’s influential dissents, naming a few that he predicted would someday become law. Then, as if anticipating such a future time, he teased the audience about the conservative positions that might win a majority of the high court — say, with a new appointment.

“Can you name some?” he said, chuckling. “Which do you want to become the law of the land? Which do you fear will become the law of the land?”