How Democrats Lost the Courts

Justice Stephen Breyer hasn’t retired yet. But filling Supreme Court seats is just one battle in a war over the judiciary—one that progressives worry they’re losing.

Merrick Garland, Stephen Breyer, and Brett Kavanaugh feature on a light-red background with imagery of the court.
Illustration by Valerie Chiang; Andrew Harnik-Pool / Getty; Pete Marovich / Bloomberg; Chip Somodevilla / Getty

Every political coalition likes to talk about how its opponents are more organized, more ruthless, and better funded. As progressives plot their response to Donald Trump’s mostly successful project to remake the federal courts, they are reviewing the times they’ve been outworked, outfought, and outsmarted on judicial nominations. One not-so-familiar name jumps out: Before Merrick Garland’s stint in purgatory, before Brett Kavanaugh’s furious denial of assault allegations, before Amy Coney Barrett’s eleventh-hour confirmation, there was Goodwin Liu.

In 2010, Democrats comfortably controlled both chambers of Congress and the White House. Liu—the son of Taiwanese immigrants, a celebrated academic, the same kind of hyper-driven polymath as a certain former senator from Illinois—was up for a seat on the Ninth Circuit Court of Appeals. At the time, Liu was also the chair of the American Constitution Society, which had been founded a decade earlier as the progressive answer to the Federalist Society, the group most responsible for the conservative movement’s intellectual takeover of the judiciary. At least on paper, Liu was a top leader of what aspired to be the foremost progressive legal network in the country. He had the enthusiastic backing of the Democratic establishment—“He’s as sharp as they come,” Senator Dianne Feinstein told the Los Angeles Times—and court watchers considered him papabile as a Supreme Court justice. If progressives had had a well-oiled judicial-appointments machine like the one associated with the Federalist Society, Liu’s nomination would have been a cinch.

But well-oiled, the progressive machine was not. Republicans set the narrative on Liu: Instead of a bright legal thinker, he was “far outside the mainstream,” then-Senator Jeff Sessions of Alabama said. A few years earlier, Liu had harshly criticized soon-to-be Supreme Court Justice Samuel Alito’s permissiveness toward policing, comments that were “vicious and emotionally and racially charged, very intemperate,” then-Senator Jon Kyl of Arizona said. Liu’s nomination languished, held hostage—along with nearly two dozen others—by Republican procedural maneuvers. In the end, it was the Obama administration that sold out its star: With the White House’s blessing, Senate Democrats struck a deal to get most of the hostage nominees through, as long as Liu and a few others got dropped.

When Democrats recite the parable of Goodwin Liu, they tell a story about Republican bad faith and foul play, but also one of their own failures. Progressives have largely ceded the judiciary to conservatives. Republicans have long been engaged in total warfare on the courts. They see liberal courts as an existential threat to the conservative project, and they have responded accordingly, building a well-funded machine to get true believers confirmed as judges. For years, Democrats never built an equal and opposite infrastructure for installing progressives on the federal bench.

The possible explanations are many: Democratic voters don’t care as much about courts as Republicans do; donors on the left didn’t invest in the courts the same way as those on the right have. But some Democrats are starting to suspect that the story is simpler: They’ve been chumps. They have clung to norms Republicans long ago abandoned. They have championed moderates in order to appeal to their enemies, only to watch those moderates twist in the wind. And they have turned up their nose at the idea that outside groups should run the judicial-nominations process, even when those groups are effective at what they do. Some progressives argue that they have honorably pursued good governance, trying to work within the federal government while their opponents turned the Federalist Society into an HR firm for Republican administrations. But grievances don’t change the facts: The conservative movement has been winning the battle for the federal courts.

After the past four years, though, some Democrats claim they are finally ready to fight for the third branch of government. They are starting with a number of disadvantages: President Donald Trump favored younger and more ideologically conservative nominees than his predecessors, and those new judges could dominate the courts for decades. His imprint on the courts is most obvious at the top, where judges’ decisions have the most sway over the definition of the law: Trump seated three Supreme Court justices, and in only one term, he appointed nearly as many influential appeals-court judges as President Barack Obama did in two. Republicans had no trouble persuading former Supreme Court Justice Anthony Kennedy, who was nominated by Ronald Reagan, to retire while the GOP held a comfortable margin in the Senate. But Stephen Breyer, whom many Democrats hoped would retire last month, shows no signs of stepping down. The 82-year-old justice embodies an earlier generation of liberal legal minds, who believed that courts could be insulated from partisan battles.

The mood among Democrats has changed, though. Over the past few years, progressive groups have set up powerful dark-money networks and advocated for starkly progressive nominees. Earlier this month, President Joe Biden bragged that his administration was “on track to have confirmed the most judges by July of the first year of a president’s first term in over 50 years.” After the long parade of indignities, the Garlands and the Kavanaughs and the Barretts and the Lius, Democrats say they’re ready to stop being chumps.

Progressives have theoretically been plotting their judicial takeover for a long time. Two decades ago, a law professor named Peter Rubin decided that progressives needed a counterweight to the conservative legal movement, which was growing in influence and power. Since the early 1980s, wealthy right-wing donors had been pouring money into the Federalist Society, which served as a clearinghouse on law-school campuses for every future scholar, judge, and public servant interested in conservative ideas. Over the course of years, the Federalist Society had come to loom over elite legal thought; it set the terms of legal debates, even for groups that disagreed with conservative principles. After the Supreme Court decided the 2000 election in Bush v. Gore, the progressive legal world mobilized against what many liberals saw as a shocking decision—and the conservative movement that made it possible.

The group they formed, the American Constitution Society, attracted some of the biggest figures—and funders—of the liberal legal world. But from the start, ACS was at a disadvantage. Although FedSoc quickly became the default home for conservative law students, progressive law students had plenty of other options for how to spend their time on mostly left-leaning law-school campuses. ACS’s money never caught up to FedSoc’s: Liberal students at ACS events got pizza dinners while conservative students hobnobbed over steaks with the judges who would soon hire them as clerks. And ACS just wasn’t focused on explicitly influencing who was in the mix for big legal jobs, including on the judiciary, in part because many progressives found the idea of an outside group influencing the president’s nomination process distasteful. Judgeship nominations were “definitely not the focus of progressives for some time,” Dawn Smalls, a former ACS board member, told me.

When Obama was elected, a glowing write-up in The New York Times cited Attorney General Eric Holder’s ties to ACS; surely, the reporter implied, this administration would move quickly to counter the conservative judicial takeover that had unfolded under President George W. Bush. Those predictions proved misguided. To be fair, a lot was happening during those early Obama years: The economy was failing, and the president was determined to pass major health-care legislation. Judicial nominations took time to source and vet, and then they took up committee time and floor time in the Senate; in this hectic legislative environment, nominations assumed a back seat. Staffers who served in the White House at the time told me the judicial-nominations process was disorganized, without clear staffing or an urgent mandate. One reason was political: “There was a sense that any time Democrats are talking about judges, they’re losing,” Chris Kang, a special assistant to the president at the time, told me. Judges were a winning talking point for Republicans who wanted to appeal to their pro-life, Christian base. The issue didn’t have as much salience for Democratic voters, who came to the party’s big tent with diverse backgrounds and priorities. Obama’s first chief of staff, Rahm Emanuel, reportedly considered fights over controversial judicial nominees a distraction from the important business of governing.

Besides, Democrats were still operating according to an old mode of politics. Senator Patrick Leahy of Vermont, the Democrat who became the head of the Judiciary Committee, decided to reinstate the so-called blue-slip process—which effectively gives individual senators veto power over judicial nominations from their state—even though Republicans had done away with the tradition when they were in power. For its first circuit-court pick, the Obama administration chose David Hamilton, a centrist judge from Indiana who was a preacher’s son and a widely admired figure in his home state, thinking Republicans wouldn’t be able to find anything objectionable in his record. Instead, Republicans painted Hamilton as a radical, anti-Christian extremist and boycotted his initial hearing. The lesson the administration took away from that experience was not that Republicans were going to oppose anyone Obama nominated; it was that they needed to pick the most moderate, palatable candidates possible if they had any hope of getting nominees through. Meanwhile, Republicans had started filibustering even district-court nominees.

By the end of the Obama years, when Democrats no longer held the Senate, confirmations had basically ground to a halt. “The Republicans just decided that whatever President Obama wanted, they were going to be against,” Neil Eggleston, who served as White House counsel from 2014 to 2017, told me. His office still tried to put nominees forward, but Republicans weren’t the only ones holding up the process. “I found that I just wasn’t getting quality names from the [advocacy] groups—and I’m not going to name them, because they’ll all call me and yell at me,” he said. Perhaps ACS once aspired to be FedSoc for progressives, but the organization had nowhere near the influence in Washington of its conservative counterpart.

By the time of Merrick Garland’s long and fruitless wait for a Supreme Court hearing, Democrats realized just how far the Republican recriminations went. Eggleston spent many hours prepping Garland for a hearing that would never happen; if by some miracle Republicans changed course, he wanted his nominee to be prepared. When the end of Obama’s term arrived and Garland was still in limbo, “I was disheartened, but not terribly surprised,” Eggleston said.

When Trump took office, progressive activists’ judgment against existing liberal legal-advocacy groups was basically universal: They had failed. As the Trump years wore on and Democrats’ panic grew more intense, new groups with urgent-sounding names started to form. Take Back the Court argued for expanding the number of justices on the Supreme Court, because conservatives had “stolen” seats among the nine. Demand Justice targeted senators whom the organization saw as out-of-touch defenders of a bygone era, including Feinstein, the lead Democrat on the Judiciary Committee. After 14 years working in the Senate and the White House, Kang, the former White House staffer and one of Demand Justice’s co-founders, came to believe that Republicans saw courts as a matter of raw power. “As much as you might want the judiciary to not be politicized, you can’t achieve that depoliticization if only one side decides to sit it out, and the other side ramps up,” he said.

How were Democrats going to get their base to care about the courts? Money. Democratic donors started funneling cash to organizations such as the Sixteen Thirty Fund, which are managed by an enormous umbrella group called Arabella Advisors. These groups were exactly the kind that Democrats had spent years decrying on the Republican side: With the Sixteen Thirty Fund functioning as a “fiscal sponsor,” groups such as Demand Justice aren’t legally required to disclose basically any information about their funders, budget, or board of directors. Since 2018, Demand Justice has spent $1.8 million on television ads and another $1 million on Facebook ads, according to Anna Massoglia, a researcher at the watchdog group OpenSecrets, and Democrats have generally outspent Republicans with dark money across all areas of politics. Leonard Leo, who helps lead an influential network of groups that work on conservative issues, including judicial advocacy, was so inspired by Democrats’ use of dark money that he restructured his organizations to mirror his opponents’, he said recently.

The explosion of dark money funding progressives’ court advocacy is uncomfortable for progressive activists to talk about. Molly Coleman, a recent Harvard law graduate who leads a group called the People’s Parity Project that pushes to limit the influence of companies and corporate lawyers in the judicial system, is part of a coalition with Demand Justice and several other groups called Unrig the Courts. Although PPP doesn’t take dark money or corporate money, “that’s just us, and we totally understand why people make other decisions,” she told me, carefully. Progressives still perceive conservatives as having the upper hand in terms of funding and infrastructure in the war over the courts, even though that’s less true now than at any time in recent memory. “Until it’s an even playing field,” it’s not worth it to try and “get the left to be ideologically pure,” Coleman said. Demand Justice says that it has recently become independent, but Kang defended its longtime secrecy: His side will not embrace “unilateral transparency,” he told me.

The biggest change—even bigger than the money and the sense of urgency—is the universe of ideas that progressives are willing to entertain. Late in the Trump administration, while all the drama over Amy Coney Barrett’s nomination was unfolding, a new idea seemed to suddenly take hold, largely thanks to this network of shadowy, communications-focused advocacy groups: The only way for progressives to regain judicial power was to add seats to the Supreme Court. Progressives justified this position by arguing that core democratic functions, especially voting rights, had been so undermined that drastic action would be necessary to save the country. Biden, a Supreme Court institutionalist, even convened a group of leading lawyers to study this and other issues, although the number of legislators who vocally support extensive court-reform measures is small. But the contrast with an earlier era of progressive legal thought was stark. A generation ago, even progressive Democrats would have seen packing the court as the absolute end of judicial legitimacy. “I, frankly, would have been appalled in the past at the idea of adding Supreme Court seats or term limits for Supreme Court justices,” former Senator Russ Feingold of Wisconsin, who took over the top job at ACS in 2020, told me. Feingold sat on the Judiciary Committee for years. He’s a norms guy, through and through. But after all that happened under Trump, “something has to give,” he said. “The right stole the Supreme Court. And there needs to be reparations for that.”

The leaders of the conservative legal movement have little sympathy for the left’s narrative about Republican intransigence. For years, these conservatives argue, the courts were biased toward progressive policy goals, and hundreds of Democratic advocacy groups united to bring down the conservative legal hero Robert Bork’s Supreme Court nomination in the 1980s. “Their sense of helplessness and victimization is a joke,” Leo told me, referring to progressives. “We wouldn’t be where we are today as a conservative movement, fighting the judges wars, if they hadn’t polarized the issue in the 1980s.” At this point, it’s not even possible to tell which side of judicial fights is better funded; the arms race of opaque money has continued unabated. But the story progressives tell about being outmatched on the courts is potentially strategic, conservatives pointed out: That narrative is useful for raising money. Members of the conservative legal movement are not impressed by progressives’ arguments for adding seats to the Supreme Court, either. “A lot of their grievances come down to, ‘Well, we didn’t win that one, and that is super outrageous to us,’” Carrie Severino, the president of the Judicial Crisis Network, a conservative advocacy organization, told me. “That doesn’t justify the level to which they are proposing to take it.”

Each side in the judicial wars is deeply invested in painting the other as a well-funded evil empire. And perhaps progressives are playing up their own helplessness to aid their political aims. Still, it’s striking that so many elite liberal lawyers are willing to say that they botched the past few decades. I asked Feingold about the chump theory of Democrats and the judiciary—whether a reflexive reverence for norms and a naïveté about power led the left to yield too much ground to the right. “It’s completely accurate,” Feingold said. “ACS is declaring, ‘The days of chumpness are over!’”

Two hours after Joe Biden was declared the winner of the presidential election in November, ACS did something that prior iterations of the organization had apparently never tried: It submitted a list of 400 potential federal judges to the Biden transition team. The staff of the incoming administration clearly had judges on their minds. A month before Biden’s inauguration, the head of counsel’s office, Dana Remus, sent a letter to Democratic senators asking for three names for every open district-court vacancy by the time Biden took office. The candidates they were looking for would be diverse not only in terms of race and gender, the letter said, but also by practice area. Instead of just the ex-federal prosecutors and Big Law partners who typically get tapped for judicial seats, they wanted labor lawyers and public defenders and civil-rights advocates. Not long after the inauguration, a group of senior staff had convened a weekly meeting to check on the progress of nominations. “There is a bone-deep feeling about the importance of the judiciary that comes straight from the top,” Paige Herwig, the White House’s day-to-day point person on nominations, told me.

Herwig’s leadership role on judicial nominations is evidence of how much more aligned the progressive legal-advocacy machine has become with this White House; before she joined the administration, Herwig was one of the first hires at Demand Justice. Republicans have noticed: Senator Chuck Grassley of Iowa has taken to questioning Biden’s nominees about whether they’ve had any contact with Chris Kang or Russ Feingold during their nomination process.

Democrats still fancy themselves to be taking the high road—that none of this is about winning. “The president feels strongly that the courts are a place where ordinary Americans go to vindicate their rights … For litigants to feel heard and like they got a fair shake in a court of law is the most important thing,” Herwig said. When I asked Senator Dick Durbin of Illinois, the current chair of the Judiciary Committee, whether Democrats have built a judicial-nominations machine to rival Republicans, he scoffed. “No one was going to get to first base with the Trump White House—even considered for an important judgeship—unless they had signed up with the Federalist Society long ago,” he told me. “We’ve not done that on the Democratic side. I hope we don’t do that. We can judge men and women based on their qualifications, without looking through their résumé for some organizational endorsement.”

The Biden administration is on the clock: For the next 18 months, while Democrats know they have control of the Senate, their mission is to fill as many vacancies as possible, as quickly as possible. In early June, Biden’s first two judicial nominees were officially confirmed by the Senate. These were not the harbingers of a new mold of progressive judges. Both candidates, Julien X. Neals and Regina Rodriguez, came out of corporate law and had been knocked by activist groups, including Demand Justice. These were revenge nominations: Neals and Rodriguez were both in the cohort of Obama picks whose candidacies withered when Republicans refused to move them through. As senators gathered to vote, Democrats hailed a new era of professional diversity on the federal bench—an aspiration, if not entirely reflected in the day’s work. The long haul is still ahead: A handful of vacancies down, roughly six dozen to fill, and only a few hundred judges to nominate and confirm before Biden can claim a judicial revolution of his own.