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Brock apologized long ago for his role as a Clinton attacker and dramatically shifted sides. Now, he is central to Clinton's run for the White House as a linchpin of her shadow campaign.
"What kind of a movement would we be if we rejected converts?" said Paul Begala, a veteran of the Clinton White House who now collaborates with Brock. "He saw the permanent intellectual and ideological infrastructure they have on the right and brought it to the left."
The man with the impressive shock of silver hair, unexcitable manner and odd personal history is prized by many veteran political operatives on the left for pushing the boundaries of modern campaigning. He's also looked upon warily by the more methodical newcomers to Clintonland who could do without the drama Brock brings.
Brock guides a network of pro-Clinton "super PACs," mega-donors and opposition researchers that operates outside the confines of federal restrictions on campaign spending. At the center is Media Matters, his decade-old nonprofit group that meticulously monitors and counters conservative media, political attacks on liberal politicians and – more recently – unflattering stories about Clinton in the mainstream press.
"What David does that is so successful is show up the mainstream media for being lazy," said former Vermont Gov. Howard Dean, who leaned heavily on Brock for help when he became chairman of the Democratic National Committee in 2005. "He forces them to confront the facts that get omitted."
Some backers of what is now a $28-million web of nonprofits controlled by Brock confess to uneasiness with the way he uses it to undermine mainstream journalists raising questions about Clinton. Brock has taken the lead in attacking the credibility of reporters who exposed the millions of dollars the Clinton Foundation collected from foreign donors while Clinton was secretary of State. An MSNBC anchor found Brock's insistence that the transactions were not newsworthy so exasperating that she finally asked him what planet he was living on.
Brock turned down requests for an interview for this story, saying that plans to promote an upcoming book have him taking a break from such conversations until closer to its publication date.
Brock made his way inside the orbit of the Clintons in the 1990s, amid his falling-out with the right. He had just published a highly anticipated biography of Hillary Clinton that conservatives hoped would destroy her career. Instead, the book offered a nuanced portrait of the then-first lady.
Clinton confidant Sidney Blumenthal saw an opportunity to turn Brock into an informant as impeachment loomed, and the besieged White House was desperate to access the enemy playbook. A mutual friend in California helped bring together the two for lunch in Georgetown, and an alliance was formed. A book Blumenthal later wrote is full of details about how skilled Brock was at going undercover for the Clintons.
Both men continue to reap dividends from the partnership.
Brock's fidelity ultimately earned him entree into a coveted group of super-wealthy liberal donors that was organized by one of Blumenthal's colleagues in the White House, Rob Stein. Stein's group, called the Democracy Alliance, was looking to a build the type of network of think tanks and political organizations that the right had so successfully created during the Clinton years. Few were better positioned to help than Brock.
"There was some angst about how credible, how believable, how steadfast a progressive David could be," Stein said. It "required a leap of faith."
Brock outperformed everyone's expectations. A seasoned Washington insider, he proved particularly adept at captivating donors, who were taken with his plans to put the machinery mastered by the right to work for the left. Stein calls him "one of the best I have ever seen" at raising money.
One tactic he used was bringing donors face to face with a nemesis.
"He interviewed me in front of all his millionaire buddies," said anti-tax crusader Grover Norquist, one of the few figures on the right who still maintains a cordial relationship with Brock. "We had a discussion about what I do, and what my thinking is.... It was a very smart way of educating his donors. He brought me in to show how tough and scary we are, that this is what he is up against."
Brock leveraged his fundraising talent into an expanded empire. By 2011, he had reinvented the art of opposition research with a super PAC called American Bridge, which sought to track every utterance of every major GOP candidate. It did so much damage to Republicans in the 2012 elections that they eventually created their own carbon copy of the organization, America Rising.
The empire continued to spread. Brock took over the board of Citizens for Responsibility and Ethics in Washington, a prominent bipartisan watchdog group. He launched another nonprofit that exists to churn out a steady stream of lawsuits accusing Republicans of ethics and campaign finance violations. Then Brock announced that he was starting yet another liberal super PAC that pushes the boundaries of election law by coordinating directly with the Clinton campaign to respond to attacks against the candidate.
As the network grew, so did Brock's indispensability to Clinton. Brock's abrupt resignation this year from the board of Priorities USA, the super PAC to which wealthy donors can channel unlimited contributions to the Clinton effort, set off panic among influential Democrats. Research from Brock's groups provides the foundation for the multimillion-dollar advertising campaigns created with Priorities cash. And key Priorities donors have long-standing personal ties with him.
Priorities lured Brock back, but not before the dispute erupted publicly. Brock accused rivals in the group of orchestrating a hit job against him. His evidence was unflattering media reports about the eye-popping fees collected by a professional fundraiser he favors.
No sooner did that controversy blow over than Brock surfaced in more Clinton-related drama. This one involves some $10,000 per month Brock's nonprofits have been paying Blumenthal, the man who welcomed him into the colorful world of Clinton loyalists two decades ago. Republicans on Capitol Hill are investigating whether Blumenthal and Brock did anything improper as they helped Clinton manage the political fallout from the attacks in Benghazi, Libya, while she was secretary of State.
Brock seems to revel in the attention. He mocked the investigating committee in a lengthy blog post, which ended with an invitation to its GOP chair to come take a tour of his office.