The fight of David Brock’s life ended on a billionaire’s rooftop overlooking Manhattan’s Upper East Side. It was election night around 9:30 p.m., and he was alone after hopping across the city for return-watching parties with wealthy donors, including investor George Soros. Standing high above Sutton Place, Brock got a text from a reporter that confirmed his creeping fears that Hillary Clinton would lose to Donald Trump. “I had my little cry, and that was that,” Brock tells TIME, before dipping into morbid humor. “It was good to be on that roof in case you had to throw yourself off.”

Brock has spent all of his adult life fighting over the Clintons, first as a conservative muckraker who discovered the sexual harassment claims of Paula Jones, sparking the fuse for Bill Clinton’s impeachment, and then as the Clintons’ chief attack dog, working with her campaign to target anyone who tried to attack her. Now it was over. “What pisses me off right now is that it looks like they won the Clinton wars,” he says.

Before election night, he had concocted a plan for what he would do if Trump won. It involved moving overseas, as so many liberals had promised, to start a new life, perhaps in London working for the public relations arm of a friend. But in the hours that followed the letdown, his plans began to shift, first with a call from the longtime Clinton adviser James Carville, then with a tearful 6 a.m. conversation with a donor, and finally with a few hours of sleep.

By the time he woke up, he had the beginnings of an answer, which he tapped out in a memo to his fundraising partner Mary Pat Bonner. The basic idea was to double down and update his organizations for the next fight, with new technology, new targets and a singular focus to hobble the Trump Administration at every turn.

He was not the only one in the vast, well-heeled infrastructure that funds the Democratic Party and progressive movement to be thinking ahead. But as is Brock’s habit, his ambitions tended to be more sweeping. For years, he has employed eight researchers whose only job was to dig up dirt and impugn the motives of Charles and David Koch, the billionaire industrialists who have endeavored to remake much of the conservative movement. Now Brock decided, once again, that he wanted to be more like those he had railed against. “Donald Trump famously threw out the political rulebook,” he wrote, in the prepared remarks for his donors. “If we are to succeed in this period, we Democrats must suspend the normal rules of politics as well.”

To make a statement, he decided to time the kickoff of this Koch-like project on the day Donald Trump was inaugurated on the steps of the capitol. Brock called together about 120 wealthy liberals at a posh hotel outside Miami for a counterevent—two days of closed-door meetings to plot strategy and raise money. The barrier to entry for donors was the ability to give $100,000, and about 20% of the group were new donors, Brock says.

The slate included a combination of new and old faces to progressive activism: Chicago Mayor Rahm Emanuel, Silicon Valley titans Mark Pincus of Zynga and Reid Hoffman of LinkedIn, along with several candidates to lead the Democratic Party and employees of Brock-controlled groups like Media Matters. “This is to fund us, plus there are half a dozen things that have to get done that we are not doing,” Brock says.

Among Brock’s plans are new efforts to shift his media-monitoring operation to focus more on smaller news websites, which often work by looser editorial standards in an effort to win converts to the conservative cause, and to pressure Facebook and Google to further clamp down on false news stories. He hopes to pivot his social-news brand, Shareblue, with a new editor who has long railed against the Democratic establishment, to become a competitor to the conservative powerhouse Breitbart. He is also seeking $8 million to $10 million more to build a legal team. “What we are going to do is use litigation as a way of tying Trump up in knots every way we can,” Brock says.

Among those who have advised him on the plan is Hillary Clinton, who suggested to Brock in a phone call after the election that he should sign up some top-notch litigators who would do pro bono work against Trump. “She spoke about trying to construct a suit that would get you discovery on potential or alleged contacts between the Trump organization and the Russian government,” Brock remembers. Brock has since been in talks with attorney Gloria Allred to help fund the defamation suit she has led against Trump on behalf of a former contestant from The Apprentice, who has said Trump made unwanted sexual advances on her.

The failures of the past year hang heavily over his new effort. During the campaign, Brock publicly boasted of his powers to stop Trump and expressed absolute confidence in Clinton’s victory. His lawyers engineered a complex arrangement where he could work with the campaign, raise money for the independent super PAC supporting Clinton and still have a hand in some of his outside groups working on election-related matters. But the efforts failed to protect Clinton’s reputation or stop Trump’s rise.

If anything, the past year further exposed the fault lines that have long existed between Brock and others in the progressive movement. The Russian hack of Clinton campaign chief John Podesta’s email revealed regular grumbling about Brock’s actions. “I truly believe he’s an unhinged soulless narcissist,” Neera Tanden, a long- time Clinton adviser who runs the Center for American Progress, wrote to Podesta in one message. (Tanden apologized in an email to Brock after the release, and their groups continue to work together.)

During the campaign, there were deep divisions between Brock and the Clinton campaign over strategy, on issues like how to treat members of the press and the best way to assail the business record of Trump. In early January 2016, Brock threatened to demand that Clinton’s rival, Senator Bernie Sanders, release his medical records, bringing a quick public rebuke from Podesta on Twitter. “The effect it had could not be understated,” Brock says. “It discouraged any kind of innovation and aggression.”

For the moment, Brock is no longer bound by such constraints, though Clinton is likely to remain a counselor to him. He has other sources for motivation. During the campaign, he was targeted with regular death threats, as was his ex-boyfriend, who owns a D.C.-area pizza restaurant that was slandered with fake news stories in what came to be known as Pizzagate. “These were far more specific and menacing and really horribly homophobic,” Brock says of the threats. The dark side of politics has become a lot darker since Brock entered the game in the 1990s. And that may help explain why his fight goes on.

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