It may be easier if we start with who you think James Edward O’Keefe III is. My guess is this will depend on your political persuasion and media diet. If you lean to the right and keep your television tuned to Fox News, O’Keefe is the YouTube generation’s preeminent muckraker, willing to enter the dregs of the liberal establishment, hidden camera in tow, to expose its hypocrisy and show how The New York Times is a mouthpiece for its socialist agenda. But if The New York Times happens to be your paper of choice and MSNBC your preferred news channel, O’Keefe is a combination patsy, Watergate burglar and sexual predator.
Either way, you probably know O’Keefe best as a pimp. That’s how I first heard of him. A little less than two years ago, friends at Andrew Breitbart’s website, Big Government, told me a couple of 20-somethings (O’Keefe and Hannah Giles, a writer for Townhall.com) had orchestrated a hidden-camera sting on the Association of Community Organizations for Reform Now (ACORN), a national community-organizing group. As part of the scheme, Giles, posing as a hooker, and O’Keefe, pretending to be her law-student boyfriend, visited ACORN offices around the country, asking for guidance on how to smuggle underage prostitutes into the country so they could use the profits to underwrite O’Keefe’s fictional political ambitions. Instead of turning them away, several ACORN employees instructed O’Keefe and Giles on how to account for their earnings on their income taxes. Once the footage—supplemented with a B-roll of O’Keefe dressed as a stereotypical pimp—was posted on Big Government, the public uproar helped tip ACORN into bankruptcy. “That 20-minute video ruined 40 years of good work,” Sonja Merchant-Jones, former co-chair of ACORN’s Maryland chapter, told The New York Times.
“This isn’t your mother’s 60 Minutes,” Breitbart proclaimed at the time. “Maybe James thinks baby boomer elites like Katie Couric, Charlie Gibson and Brian Williams could care less. Their generational zeitgeist—and the knowledge that their kids are personally immune from monster deficits—is all that matters. And they look the other way while believing all organizations on the left—no matter how extreme—are working toward their goals.”
In the ensuing 18 months I have personally witnessed O’Keefe’s rapid rise to Tea Party superstardom and subsequent excommunication. Although I didn’t meet him until after the ACORN footage went live on Big Government, I know most of the people inside our small community of political consultants. I teach political technology at the Leadership Institute, a finishing school for Karl Rove types where O’Keefe once worked. Given that O’Keefe’s generational zeitgeist encompasses Johnny Knoxville, social media and rabid distrust of the establishment, I consider him an ace performance artist–political shit stirrer–jackass. He is fearless, engaging and as paranoid as Richard Nixon. (I am convinced he furtively recorded all our meetings and conversations.)
He also possesses awful judgment, which is why numerous former allies refuse to go on the record. These days they want nothing to do with O’Keefe. After ACORN, a series of embarrassing duds forced many O’Keefe advocates to distance themselves from him. In late January 2010 he attempted to tamper with Louisiana senator Mary Landrieu’s phones, a high-risk, low-reward stunt that landed him in a New Orleans jail. Eight months later a ridiculous plan to seduce CNN reporter Abbie Boudreau aboard O’Keefe’s sailboat unraveled at the last minute, and Breitbart cut him loose. “From what I’ve read, this script, though not executed, is patently gross and offensive,” Breitbart scolded. “It’s not his detractors to whom he owes this public airing, it’s to his legion of supporters.” O’Keefe claims his public banishment is bullshit and that his relationship with Breitbart has merely evolved. I’m not so sure.
Chronicling O’Keefe’s life in detail is usually off-limits to anyone outside his tiny corner of political professionals and paranoid activists. “The mainstream media always has made the story about us—how much money it costs to do what we do and how other journalists perceive what we do,” O’Keefe responded to my overtures for an interview. “Even in the most wildly successful case, when Congress was taking action after our videos, The New York Times wanted to profile me but not do a political story. My challenge is to get the media to cover the substance of what we do. Do you understand my burden and reluctance to do an interview with Playboy?”
Ever since, he has sent me e-mails about how the Times and other mainstream media organizations are out to get him by covering his arrest on the front page but ignoring his successes. But because we inhabit the same circles, he eventually relented and let me into his world—albeit in his own uncomfortable way—so I could see if anyone really knows who he is.