Brian Fallon was once one of the most sought after operatives in Democratic politics: a brass knuckle brawler with experience at the highest levels of government, a cellphone filled with the top journalists in town, and a reputation for being preternaturally on message.

Most offices would have died to hire him. But that was before he decided to devote his career to making the courts more progressive—and to doing so with little care for who he pissed off along the way. Now, many top Democrats can’t stand him.

“I get two varieties of responses,” Fallon said of the reception his judicial advocacy gets among his Democratic brethren on the Hill. “Obviously, some of these Democratic senators that we’ve been not shy about calling out, hate it. I’ve been disinvited from a lot of meetings that I used to get invited to on the Senate side of the Capitol. On the other hand, I hear privately all the time from people that say I can’t have anything to do with this but I’m glad somebody’s doing it.”

“ I’ve been disinvited from a lot of meetings that I used to get invited to on the Senate side of the Capitol. On the other hand, I hear privately all the time from people that say I can’t have anything to do with this but I’m glad somebody’s doing it. ” — Brian Fallon

Under the informal codes of Washington D.C., one is usually exiled from establishment circles only after episodes of personal or professional humiliation. And even then, an excommunication usually proves temporary. But Fallon’s path from top flight communicator—press secretary for, among others, Sen. Chuck Schumer (D-N.Y.), Attorney General Eric Holder, and presidential candidate Hillary Clinton—to persona non grata for many in elected office was for a different reason entirely. He chose it.

In the wake of that Clinton loss, he started the progressive organization Demand Justice in the spring of 2018. In theory, it was dedicated to stopping President Donald Trump’s judicial appointments. But in practice it’s been about redirecting the Democratic id as it pertains to the judicial wars. The group has rattled many Democratic senators who, Fallon believes, are supporting the president’s judges as an olive branch to Republicans or out of some bygone commitment to courtesies and norms. The group has issued report cards going after Democratic senators’ voting patterns, run ads calling out Democrats who vote with Trump the most, and pushed progressives to embrace new liberal priorities like getting rid of the legislative filibuster and expanding the Supreme Court.

It’s not gone unnoticed on the Hill, where mention of Demand Justice can elicit fiery—bordering on incensed—responses from lawmakers and their staff. Nor has it gone unnoticed by Hill veterans, who wonder whether Fallon’s strategy of antagonizing fellow Democrats is productive or respectful.

“Maybe I’m old-fashioned but sometimes I find his willingness to criticize the leadership, including his former boss, a little off-putting,” Jim Manley, a veteran of the Senate told The Daily Beast. Manley described Fallon as the best Schumer press secretary he’s ever dealt with who not only knew politics but the nitty gritty of policy. “Brian obviously believes in what he’s doing but I find it sometimes a little surprising how much he’s willing to criticize the Democratic leadership which includes his former boss.”

But Fallon doesn’t mind angering a few of his fellow Democrats. In some ways, he views it as a legitimate and useful part of the brand, even embracing the notion that he’s gotten more “radical.” His drift from establishment flack to establishment antagonist, he says, has more to do with the politics of the moment—when his party is reimagining what governance truly is—than his own personal journey. His contemporaries agree.

"I remember sitting at a bar with Fallon when he started talking about SCOTUS reform, and giving him shit for being radicalized—he said it wouldn't be a radical position in two years when we were all frantically refreshing Twitter, praying John Roberts would save Obamacare again or stop Roe from being overturned by partisan hacks,” said Jesse Lehrich, a former Clinton campaign staffer close with Fallon. “That day doesn't feel so far away now."

Fallon didn’t immediately know what to do with himself after Clinton lost a razor-thin election to a man she and her staff warned was an existential threat. Like many who worked on her campaign, he had assumed she would be the first female president up until the campaign began receiving election returns at 8:30 P.M. on November 8, 2016.

That night, he had stayed up until around 4 A.M. working with the Clinton staff in a Peninsula hotel room devising remarks for the following day. He ended up walking to a different hotel where he was staying, which brought him directly in the path of the Hilton Midtown, outside of which people in Make America Great Again hats were exulting in their victory.

The next day, at the site of Clinton’s concession speech, Fallon was asked by another staffer what he was going to do next. “I have no idea,” he responded. Later in the day, he was back at the campaign’s Brooklyn headquarters where members of the communications team gave speeches to buck up the group. Fallon told those assembled that he believed they’d end up on the right side of history and that they’d helped pave the way for a future woman president.

It was self-assurance too. Fallon had plans for a Clinton presidency that were now scrapped and a sense of personal failure that he had to grapple with.

At first, he stuck with what he knew best: operating at the high-end of conventional Democratic politics. He joined the party's biggest super PAC, Priorities USA, scored a gig on CNN, and offered pearls of warmed-over punditry, such as theories that Democrats would find political nirvana by winning over disaffected Republicans in the suburbs. He took meetings and entertained various career opportunities: from political consulting to running comms for a Fortune 500 company.

But he gradually became irked by how quickly many Democrats expressed willingness to work with the incoming Trump administration. During the campaign, they’d called Trump a threat to the foundation of the United States. But within days of the election, some were already positioning themselves to cut legislative deals with him. Nowhere was this more apparent than in the willingness of some Senate Democrats to greenlight Trump’s judicial appointees.

“This seemed like an issue where Trump was having an immense impact, in fact arguably going to be his biggest legacy beyond the tax legislation or anything he’s done administratively,” Fallon said. “You have these Democrats, some of whom now want to run for president, that present themselves as champions on climate change or champions of reproductive rights but they’re voting for huge swaths of Trump appointees that when those cases touching those issues reach them they’re going to rule exactly the wrong way. Why is that viewed as acceptable?”

“ You have these Democrats, some of whom now want to run for president, that present themselves as champions on climate change or champions of reproductive rights but they’re voting for huge swaths of Trump appointees that when those cases touching those issues reach them they’re going to rule exactly the wrong way. Why is that viewed as acceptable? ” — Brian Fallon

Fallon saw that activist-driven movements were having a strong impact on lawmakers, particularly in ginning up opposition to President Trump’s Muslim travel ban and the fight against the repeal of the Affordable Care Act. And he decided that such a model was sorely missing from the Democratic Party’s agenda for the courts.

For decades, Republicans have prioritized turning the judiciary conservative. The foundation of the Federalist Society in 1982 was predicated, in part, on the notion that Court rulings had codified the liberal agenda and that only a counter reaction would help undo the damage. The GOP prioritized both the development of young, conservative legal talent and the immersion of that talent into and throughout the judiciary. It was a massive project that culminated in the most brazen of political acts: Senate Majority Leader Mitch McConnell’s (R-KY) decision to deny Barack Obama’s Supreme Court nominee, Merrick Garland, a vote.

For many, that (successful) gambit removed any lingering suspicion that the judicial branch was immune from partisan squabbling. For Fallon, it was an epiphany: opening his eyes to how operatives like him needed to think of political change on generational scales.

“On our side,” he said, “we tend to have more people that fashion themselves the next James Carville or at least want to be that as opposed to thinking of themselves as a movement progressive whose goal, whose timeline, is not the next two years but who is thinking about how we can shift the window and move the landscape to the left over a 10- or 20-year time horizon.”

Fallon’s career path was pretty much a straight line through establishment institutions before a dramatic turn left. In the early 2000’s, he was writing about sports for the Harvard Crimson, before going on to work on John Kerry’s 2004 presidential bid. By 2006, he he’d gone to the Senate where he served as press secretary for Sen. Bob Menendez (D-NJ) and then Schumer. Before moving to the Justice Department in 2013, Fallon had accrued almost a decade of experience in Democratic politics and had married Katherine Beirne, who went on to serve as the White House director of legislative affairs for President Obama.

Those who have worked with Fallon described him as a fastidious colleague, someone who could effectively steer stories for his employers. Reporters would occasionally complain of his prickliness and his reputation for publicly bashing stories that either he or the campaign hated. Multiple reporters said he often served as one of the top enforcers on the campaign’s comms staff, pushing back against tough stories. But even his competitors appreciated his craftsmanship.

“Brian and I don’t always agree, but I watched a lot of his tape in 2016 and without a doubt he’s one of the best communicators I’ve ever seen,” Mike Casca, a former spokesperson for Sen. Bernie Sanders (I-VT) said. “If you gave him any daylight, he saw it and knew exactly how to maximize the pain.”

“ Brian and I don’t always agree, but I watched a lot of his tape in 2016 and without a doubt he’s one of the best communicators I’ve ever seen ” — Mike Casca

His work ethic was memorable. During the 2016 campaign, Fallon would take a bus on Fridays from the headquarters in New York back to Washington, D.C., to be with the couple’s newborn twins on the weekends. On Mondays he would come back early, often jumping on the campaign’s weekly communications call while on the bus back.

“Actually we kind of joked that during the week that’s when he was able to catch up on his sleep,” Karen Finney, a former spokesperson for the campaign said.

Fallon himself was acutely aware of his image as a bit of a mercenary that he’d built throughout his career. And didn’t particularly care for those who sought to dispel it.

"I remember once, BuzzFeed did these silly profiles on a bunch of us in 2011 and 2012,” Adam Jentleson, former deputy chief of staff to Sen. Harry Reid (D-NV) told The Daily Beast. “Young congressional staffers. It was Brian, me, Brendan Buck and Brad Dayspring. Each of us talked to the reporter for the other person. I said something like Brian had a heart of gold. And he was never more mad at me than when I said that. He wanted to be seen as this hard-bitten operative.”

As he has moved from the world of partisan politics to more overt activism, Fallon hasn’t lost the pugnacity that defined him. If anything, he’s used it to his advantage: applying his knowledge of the Senate to his efforts to try and influence those who remain in that chamber.

One of Demand Justice’s first campaigns tackled an issue largely off the radar of the vast majority of the public but deeply consequential to both the courts and the average Senators’ sense of personal and institutional self worth. McConnell had announced his intent to dispense with the concept of blue slips, the process by which a judicial nominee’s home state senator got to sign off on advancing their nomination. The group attacked him vigorously. But it did so with a twist: demanding that no Democratic Senator at all vote for any nominee if she or he did not have the blue slips returned.

One of the group’s most recent campaigns is to focus attention on a slew of anti-abortion laws being passed in states across the nation. But instead of just hammering state lawmakers for supporting those measures, Fallon has placed part of the onus on national Democrats for backing the judges who could uphold the constitutionality of the effort.

As the 2020 elections approach, Fallon seems more keen on aggressively calling out Democratic senators by name. And among his favorite pinatas appears to be Sen. Michael Bennet (D-CO), a moderate who has voted the most frequently for Trump’s judges among the massive field. In March, the group published a report card grading Senate Democrats on their voting record for the president’s nominees. Bennet earned an “F,” largely for not joining the Democratic filibuster of Justice Neil Gorsuch (the senator argued that the caucus should have waited to use that procedural tool for the nomination of the next justice, who turned out to be Kavanaugh). When Bennet announced a presidential bid two weeks ago, Demand Justice responded by launching an ad campaign against him in New Hampshire.

Bennet, in a recent Meet the Press interview, said Demand Justice itself “deserve[d] an ‘F’”—a bit of pushback that seemed to do little more than delight Fallon.

“[He] wants to look reasonable to a panel on Morning Joe and the Washington Post editorial board,” Fallon said of the senator.

A Bennet campaign spokesperson responded by calling the war of words, a “fundraising gimmick for a dark money Super PAC, not a real strategy to protect the independence of our judiciary or the interest of the American people. Michael is sick of losing as McConnell and Trump rack up judge after judge.”

That Fallon spends a good chunk of his days calling his fellow Democrats squishes isn’t lost on him. Nor is he entirely unmoved by the argument that his time would be better spent focused on Republicans exclusively. It’s just that he no longer buys into that worldview. If anything, he’s grown more convinced that the lack of political willpower of the “centrist go-along, get-along Democrat[s]”—as he calls them—is the fundamental hurdle Democrats face.

“I suppose we could take the very dog bites man approach to focusing attention on Republicans,” he said. “But no one would be surprised or fault Republicans for voting for judges that they agree with. The twisted thing that’s going on is Democrats are voting two-thirds of the time for judges that they don’t agree with.”

Being a professional pain in the ass for the Democratic Party is not cost free, of course. And as Fallon has embraced his new role, his old colleagues and bosses have not always embraced him. In particular, his work has damaged his relationship with Schumer, who earned a “C” in Demand Justice’s first report card on judicial appointees.

Multiple people told The Daily Beast that the Minority Leader, who spoke at Fallon’s wedding, no longer talks to his former top communications staffer. When asked about his relationship with Schumer, whom he doesn’t directly criticize, Fallon declined to “answer any questions about Chuck.”

Then he proceeded to answer with effusive praise.

“I learned from him more than I’ve learned in any other job,” he said. “It was the most instructive opportunity and experience I’ve ever had. And I greatly respect and admire him. I’m not going to do any other analysis or grading of his performance as Leader.”

Those who know Fallon say that they’re not terribly surprised by his turn away from the establishment. For them, it’s more akin to an awakening than an evolution.

For years, Fallon and other operatives of his age functioned under the idea that politicians needed to work within the realm of the possible. Those who drifted outside of those constraints were deemed hopelessly naive at best, and irritating idealists at worse. Then Donald Trump happened, and the idea that governance was about trade offs, incremental changes, and backroom deals, seemed itself to be painfully meek.

“He was investing faith in the ability of the system to work and then he saw that faith blow up in his face,” Jentleson said.

But, of course, there are still people who operate within that “system”—the Schumers and Bennets of the world who, while in the minority, still have levers of power to pull, platforms to push, and stages to occupy. And while Fallon may be a liberated, even radicalized, man outside of that system, he is still on the outside.

"We’re not going to be able to help with your Fallon story," is all that Justin Goodman, a spokesperson for Schumer, would say when asked for a response.

With reporting by Sam Stein