First He Went After Anita Hill. Now He’s Coming for Clarence Thomas.

David Brock speaks calmly and deliberately, exuding the kind of knowingness you would expect from someone who has been immersed in Washington politics for decades. But in 2004, when he started Media Matters for America, the left-leaning advocacy group that monitors the right-wing press, he encountered a situation he wasn’t quite prepared for.

“Our liberal researchers would debate whether they were being fair to Rush Limbaugh,” Brock recalled recently, referring to the ultraconservative radio host. Media Matters had little trouble finding instances of Limbaugh saying outrageous things — in any given episode there was a decent chance he would call a woman a “feminazi” — but Brock’s young staffers were earnestly discussing their moral obligations: “Let’s not rip it out of context. Let’s be fair and portray what he’s saying accurately.” Brock laughed, remembering how incredulous he was.

“Coming from the right, that was a shocking concept to me, that you were trying to be fair.” After all, Brock made his name in the 1990s as a journalist for whom fairness was not much of a priority. He was a proud conservative then, writing high-octane hit pieces that gleefully mowed down liberal targets. Among his career-defining coups was “His Cheatin’ Heart,” a 12,000-word 1993 article for The American Spectator in which Arkansas troopers dished about President Bill Clinton’s alleged sexual assignations when he was governor of the state. Christened “Troopergate” by the media, the story Brock broke became one more scandal in the lurid chain leading to Clinton’s impeachment in 1998.

By then, Brock had renounced his past as a “right-wing hit man” in an essay for Esquire, declaring that his Troopergate story had “launched the print equivalent of poison-gas canisters on the Clinton White House.” The essay featured a photo of Brock lashed to a tree and staring moodily into the distance, ready for his auto-da-fé.

Even in our age of political disarray, Brock’s tortuous trajectory stands out. Here is someone who went from having “conspired to damage you and your presidency,” as he confessed in an open apology letter to Bill Clinton; to allying himself with the Clintons; to founding the Democratic super PAC American Bridge in 2011; to being a vocal surrogate for Hillary during her presidential run in 2016. He quickly proved his formidable skills at creating organizations, political strategizing and raising money.

But earning trust — perhaps the most valuable currency of all — has been stickier. His political journey to the other side of the aisle has been anything but smooth; he continues to be a lightning rod, not just for the right but also for those on the left who recoil at his evident comfort in the shadowy world of opposition research and dark money. His attempts to redeem himself are bedeviled by his enduring fascination with the machinations of political power.