Filmmaker James O'Keefe and friend Hannah Giles, dressed in costume as a pimp and prostitute respectively, pictured at the Washington Monument.

James O’Keefe’s Most Infamous Stings: A Retrospective

O'Keefe may have a lifetime of pranks to show for himself, but three stand out: ACORN, CNN and NPR

READ OUR EXCLUSIVE PROFILE OF JAMES O’KEEFE HERE

James O’Keefe’s inflammatory political punking began at Rutgers with the launch of his conservative journal, The Centurion, and a variety of on-campus pranks, including running an affirmative-action bake sale. But it’s his post-graduation stunts—Project Veritas’ ACORN sting of 2009, O’Keefe’s attempted CNN takedown of 2010 and his 2011 NPR bust—that continue to make waves for their calculated, humorous and (mostly successful) infiltration into mainstream political life. Below, a look back at O’Keefe’s most controversial stings:

ACORN

What was it?

O’Keefe launched his most controversial—and ultimately most successful—sting in early 2009: a large-scale takedown of Association of Community Organizations for Reform Now (ACORN), one of the government’s pre-eminent poverty advocacy groups. Dressed as a pimp, O’Keefe traveled to ACORN offices across the country with activist accomplice Hannah Giles, dressed as a prostitute, to question the government group’s employees about tax issues, child prostitution and founding a brothel. The pair (who met on Facebook, according to The New York Times) taped their conversations with low-level ACORN workers, immortalizing their efforts to help the pimp-prostitution team evade the law.

Why was it controversial?

Published in September 2009, O’Keefe’s videos spawned a slew of government investigations into individual ACORN offices, ACORN’s funding and the legitimacy of O’Keefe’s heavily edited clips. Already under fire from conservative groups for its voter registration practices, ACORN slowly disintegrated, and with little funding left over after O’Keefe’s sting, the government group filed for bankruptcy and officially disbanded in April 2010. Meanwhile, O’Keefe and Giles won the support of publisher Andrew Breitbart, who indoctrinated O’Keefe as his protégé and gave the pair a large stipend to pursue related stings.

CNN

What was it?

In August 2010, CNN reporter Abbie Boudreau sought to interview O’Keefe as part of a documentary on young conservative activists. O’Keefe, hesitant to meet with Boudreau and to let her into his “inner sanctum,” scheduled a preliminary interview with the journalist at his home in suburban Lusby, Maryland. After reaching an agreement regarding the pre-interview, Boudreau traveled from New York to Lusby, where she was met by Project Veritas activist Izzy Santas, one of O’Keefe’s confidants. With O’Keefe nowhere in sight, Santas alerted Boudreau of O’Keefe’s plan to punk the reporter, staging an interview on his boat behind the house. The boat, Santas told Boudreau (and later confirmed by documents obtained by CNN), would be monitored by hidden cameras and would be filled with prank items such as a “condom jar, dildos, posters and paintings of naked women” in order for O’Keefe to hit on—and make fun of—Boudreau and the news organization. Realizing Santas had revealed his plan, O’Keefe ultimately emerged from the boat where he was hiding, and Boudreau departed shortly after without an interview.

Why was it controversial?

Following his successful ACORN sting, the attempt to entrap Boudreau proved to be a damp squib and ultimate failure. Media outlets slammed O’Keefe for his highly sexualized stunt, citing that “none of it made any sense.” Andrew Breitbart, O’Keefe’s mentor, admonished him for the flop, telling the sting artist he owed the world a “candid and public explanation” for his plot.

NPR

What was it?

In March 2011, O’Keefe disguised two of his hit men as representatives of a U.S.-based front group for Egypt’s Muslim Brotherhood, the Muslim Education Action Center. The two met for lunch in Washington, D.C., with Ron Schiller, NPR’s former senior vice president for development, and Betsy Liley, NPR’s senior director of institutional giving, with plans to hand over a $5 million check to the news organization. Prompting the NPR executives with questions about their funding, O’Keefe’s operatives recorded Schiller slamming conservative groups, citing that “the current Republican party, particularly the Tea Party, is fanatically involved in people’s personal lives, and very fundamentally Christian.” He continued: “It’s this weird evangelical kind of move,” adding that the Republican party had been “hijacked” by “seriously racist, racist people.”

Why was it controversial?

At the time of O’Keefe’s sting, NPR received $90 million in federal tax money, making Schiller’s slams of Conservatives in office particularly inflammatory. O’Keefe’s stunt forced Schiller, along with Vivian Schiller, then NPR president (unrelated to the vice president), to resign. Blaze editor-in-chief Scott Baker subsequently reviewed O’Keefe’s published video, shown above, with his raw footage, ultimately determining that O’Keefe had set out to “intentionally” confuse his viewers.

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