PART ONE The Choice
CHAPTER ONE The Missing Man
In the summer of 2016, Brett Kavanaugh was celebrating his tenth year on the bench, and his growing ranks of law clerks had gathered for a reunion. This one, held in June at the Chevy Chase Club, not far from Kavanaughâs home, came at an odd, even awkward moment, with Donald Trump about to claim the Republican nomination. Some of the clerks were Democrats, and though more were Republicans, few if any were Trump Republicans. All of them, it is safe to say, had been astonished a few weeks earlier when Trump released a list of eleven potential Supreme Court nominees that was notable for the name it did not include: Brett Kavanaugh. By this stage in his career, Kavanaugh was an obvious if not leading choice for any Republican president or presidential contender. He had been on Mitt Romneyâs short list for the Supreme Court during the 2012 campaign and no doubt would have been at the top of the roster for any of the establishment GOP candidates in 2016, such as Jeb Bush and Marco Rubio, except that they had long before fallen to Trump.
Still, at that point the prospect of the blowhard New York reality television star actually winning the presidency seemed fanciful. So when Travis Lenkner, an early Kavanaugh clerk who was serving as master of ceremonies for the event, referred to Trumpâs glaring omission, it was more in the nature of gentle joshing than painful jab. Hereâs to Judge Kavanaugh, he toastedâthe twelfth man on Trumpâs eleven-person list.
Trump had been toying with the notion of that list for months before the plan became public. Before the Iowa caucuses, when New Jersey governor Chris Christie, at the time a Trump rival but also a friend of long standing, asked Trump how he was going to manage the problem of attracting evangelicals, Trump threw out a suggestion: what about getting the Federalist Society to produce a list for him? Good idea, Christie responded; you should talk to Leonard Leo. Trump wasnât going to secure the nomination, he figured, so offering Trump advice was like giving away snow in winter.
Ted Cruz, the conservative senator from Texas, came in first in the Iowa caucuses on February 1, thanks in large part to his support among evangelicals, the very constituency that Christie had identified as a Trump vulnerability. Trump won the New Hampshire primary eight days later. Then came the event that upended the campaignâand, as it played out, helped catapult Trump to victory. Don McGahn, the Trump campaignâs general counsel and, in his spare time, guitar player for a rock-and-roll cover band, was on his way to a gig that Saturday afternoon when he received a text from his wife: âScalia died.â1 McGahn pulled to the side of the road to collect his thoughts. There was a primary in South Carolina that night, and the candidate needed to be prepared for questions on this new front.
Scaliaâs death generated an instantaneous miniversion of the Trump listâand the first inkling that Kavanaugh might have a problem making it. As Trump did his once-over-lightly form of debate prep later that dayâforty-five minutes in a room with key advisers as well as others who called inâMcGahn pressed the point: the candidate couldnât simply rely on a generic pledge to name a justice in the Scalia mold. That wouldnât be convincing, not from Trump. Voters listening to the debate wouldnât have any worries about Cruz filling Scaliaâs seat, McGahn argued. Trump, on the other hand, was an unknown, and untrusted, quantity. He had been, not so long ago, in favor of abortion rights and a ban on assault weapons. He needed to back up his promises with some specifics. So that evening, when moderator John Dickerson of CBS raised Scaliaâs death as the first question of the debate, Trump not only echoed McConnell in calling for âdelay, delay, delayâ until a new president could be elected, he also took the unusual step of volunteering names of those he would consider for the vacancy. âWe could have a Diane Sykes, or you could have a Bill Pryor, we have some fantastic people,â Trump offered. Those names were significantâa calculated signal to the conservative base that Trump would pick judges to their liking.2
Sykes, a former justice of the Wisconsin Supreme Court named to the Seventh Circuit by George W. Bush, was a darling of social conservatives for, among other things, striking down the Affordable Care Actâs requirement that employers provide no-cost contraceptive coverage, a mandate that Sykes said infringed on the religious freedom of Catholic business owners.3 She had attracted the attention of McGahn, an election lawyer who detested campaign finance regulation, with a ruling striking down major parts of Wisconsinâs campaign finance law on First Amendment grounds.4 (After the election, Sykes made it to a first-round interview with the presidentâs advisers. But Trump was put off by her marriage to a leading Republican Trump critic, talk radio host Charlie Sykes, although he kept forgetting the key fact: the Sykeses were divorced.)
Pryor, a former attorney general of Alabama tapped for the Eleventh Circuit by Bush, was even more controversialâand therefore an even more potent signal for Trump to send to conservatives. Among other things, Pryor had dismissed the Supreme Court as ânine octogenarian lawyersâ and criticized Roe v. Wade as âthe day seven members of our highest court ripped the constitution and ripped out the life of millions of unborn children.â5
As McGahn later described Trumpâs approach to the debate, âI knew then that President Trump was a different kind of guy. For him to go up in a debate and say âJudge Pryorâ showed me he was the real deal when it was going to come to judges. There was no hesitancy. There was none of this, âWell, you know, who are the moderates?â â6
There was one name McGahn floated on the night of Scaliaâs death, as his candidate did his debate prep, that Trump waved off. No one from the swamp, Trump instructed. That meant no Kavanaugh.
There was another, related problem as well. âWhen people think of Brett,â one campaign official explained, âthey think of Bush.â That was not exactly a plus in Trumpworld, and certainly not with the candidate himself. Jeb Bush, the brother of the president for whom Kavanaugh had worked, was still in the raceâhe dropped out a week laterâand even after that the hostility between the Trump and Bush camps festered.
Scaliaâs deathâand McConnellâs vow to hold the seat open for the next presidentâtransformed the campaign equation. For voters in the Republican baseâfar more than for Democratsâcourts, and the Supreme Court in particular, are always a motivating force. These voters are tired of what they view as unelected judges writing policy preferences into constitutional law. For decades, these liberal judges prevented ordinary citizens from protecting the lives of the unborn and from allowing their children to pray in school. Now they were trying to tell them not only that gays and lesbians had a constitutional right to marry but also that a baker whose religion held that same-sex marriage was sinful had to bake a cake to celebrate the marriage or else be put out of business. Now Scaliaâs death brought those concerns to the forefront. Hillary Clinton could not be permitted to replace Scalia with a liberal justice.
The future of the court was comfortable terrain for Cruz, a Harvard-trained lawyer, clerk to Chief Justice William Rehnquist, and former Texas solicitor general. The Texas senator was delighted to exploit the issue not only against Clinton but also, more immediately, against Trump. And he had a handy weapon to wield against his rival: Trumpâs sister Maryanne Trump Barry. Older than Trump by nine years, Barry was a veteran federal judge, first appointed to a federal trial-court judgeship by Reagan and elevated to the Third Circuit in 1999 by Bill Clinton. Trump had raised the prospect of tapping his sister for the high courtââjokingly,â he insistedâand managed to dig himself into an even deeper hole with social conservatives.7
âI think sheâd be phenomenal. I think sheâd be one of the best,â Trump told Bloomberg Politics in August 2015 about the idea of his sister as a justice. âBut frankly, weâd have to rule that out now, at least temporarily.â Again, in October 2015, he told Fox News about the idea of naming his sister to the high court, âI would love to, but I think she would be the one to say, âNo way, no way.â â8
Trump may have been joking, but conservatives were not amused. Barry was anathema to conservatives for a 2000 ruling in which she struck down a New Jersey law banning the procedure known as partial-birth abortion. The Supreme Court had just overturned Nebraskaâs nearly identical law, but that didnât matter.9 Conservative activistsâand Trumpâs Republican rivalsâstill railed against Barry.
Trumpâs âbreezy adulationsââphenomenalâ and âone of the bestââgloss over the reality that Barry is a pro-abortion judicial activist,â warned Carrie Severino of the Judicial Crisis Network, the Leo-linked group that eventually fell into line and spent millions of dollars promoting Trumpâs Supreme Court picks after the election. In a USA Today op-ed piece headlined DONâT TRUMP THE SUPREME COURT, she cautioned that Trump âhas yet to prove that he can be trusted with that most precious of presidential powers: the power to shape the high court.â10
Likewise, conservative activist Penny Nance of Concerned Women for America called Trumpâs praise for his sister âalarming and disturbing,â adding, âThat Mr. Trump can so easily offer effusive praise of a judge who is in favor of giving constitutional protection to partial-birth abortionâsimply based on the fact that the judge is his siblingâcalls into question not just his readiness to be the nominee for the party that fights for the unborn, but his overall fitness for the most important job in the world.â11
In the days after Scaliaâs death, Cruz flayed Trump for the comments about his sister. A âBill Clintonâappointed federal appellate judge who is a radical pro-abortion extremist,â Cruz said.12 For Trump, producing that list, and getting it right, was going to be more important than ever.
By the end of March, Trump was improbablyâalarmingly, to much of his partyâon the verge of clinching the GOP presidential nomination. But he faced the same vexing problem he had discussed with Christie in Iowa: winning the trust of social conservatives and persuading them to turn out for him in November. On a triumphal trip to the capital as the partyâs all-but-certain nominee on March 21, Trump visited the Washington Post for a session with the editorial board, unveiling a list of foreign policy advisers and, ever the real estate developer, complimenting the newspaperâs gleaming new offices. He toured the new Trump International Hotel under construction on Pennsylvania Avenue, touting its granite exteriorââthey donât build them like that anymore, that I can tell youââand the cavernous lobby, soon to be adorned with âmarble, beautiful marble, from different parts of the world.â13 He pledged fealty to Israel before the American Israel Public Affairs Committee, assuring the crowd, âMy daughter Ivanka is about to have a beautiful, Jewish baby.â14
And he convened a group of conservative lawmakers and activistsâincluding Alabama Republican Jefferson Sessions, the first senator to endorse Trump; Heritage Foundation president and former South Carolina senator Jim DeMint; and former House leaders Newt Gingrich and Bob Livingstonâto help him tackle the conservative problem.
âThe meeting wasnât philosophical. The meeting was political,â Gingrich recalled of the session in a conference room at Jones Day, McGahnâs law firm. âThe meeting wasâthere are a large number of conservatives who are still not convinced youâre a conservative. What can he do to reassure people that heâs really a conservative?â15
Judges were the obvious answer, and Trump now floated his audacious solution before the group: releasing a list of prospective Supreme Court nominees. Under normal circumstances, with normal presidential candidates, such short lists of potential nominees are closely guarded secrets. Trump turned that convention on its head, much to the discomfort of some of his advisers. It wasnât having the list that mattered, as Trump saw the situationâit was making the names public. âI donât think any experienced politician would have done that,â said Trump adviser and former New York mayor Rudy Giuliani. âBut heâs different. And I think he felt because Iâm different I have to do things differently to satisfy people that I know what Iâm doing.â16
Trump, never a man to keep a secret, telegraphed his plans later that day in a news conference held amid the construction of the Trump hotel. âIâm gonna submit a list of justices, potential justices of the United States Supreme Court that I will appoint from the list,â he said. âI wonât go beyond that list. And Iâm gonna let people know. Because some people say, maybe Iâll appoint a liberal judge. Iâm not appointing a liberal judge.â17
As the group discussed the judges list, the Heritage Foundationâs DeMint volunteered his organizationâs services in putting together some names. But one man in the room that day had come forewarned by McGahn of Trumpâs desire to have a list and was forearmed with a roster of names. The Federalist Societyâs Leo stayed behind after the gathering broke up to speak with Trump and McGahn. He reached into his jacket pocket and pulled out a list of six possibilities.
âI was really hoping for twelve,â Trump told him.
âWe can try,â Leo replied.18
Leoâs answer was telling. As Trump pressed him to come up with more names, there was one obvious candidate whom Leo nonetheless omitted. Once again, Kavanaugh was the missing man.
Kavanaughâs absence from Leoâs list was no accident. Kavanaugh and Leo had known each other for years; they had worked together on judges back when Kavanaugh was at the Bush White House. But privately, Leo harbored concerns about the reliability of Kavanaughâs conservatismâworries prompted by, but not limited to, the fact that Kavanaugh had demurred a few years back, when he had the chance, to vote to overturn Obamaâs signature health care law.
Leo âdidnât trust that Brett wasnât going to pull a Souter because of his background, being a swamp creature, born and raised in the D.C. area, being very much a Bush Republican,â said one close observer. âAll the credentials ⌠pointed to someone who was high risk.â
Those worries werenât well known outside conservative circles, butâmuch as his Bush ties served as a black mark with Trumpâthey threatened to keep the well-credentialed jurist from the Supreme Court seat that he had long coveted.
Well before the meeting at Jones Day, the Federalist Society had become the conservative movementâs established clearinghouse for legal talent. For Trump, the Federalist Societyâs imprimatur served as a kind of Good Housekeeping seal of approval for judicial nominees. If the Federalist Society blessed Trumpâs picks, conservatives could relax.
Not in their wildest, most ambitious dreams did the founders of the Federalist Society imagine that their group would eventually wield such influence when they organized their first event, held at Yale on the last weekend of April in 1982. âA Symposium on Federa...