Jack Cashill floats a theory that Barack Obama is a fraud

I would be surprised to learn of a better investigative reporter ever than Jack Cashill,” writes an admirer on the conservative news site World Net Daily. A reader of the liberal blog Wonkette is less impressed: “Whoever is in charge of Jack Cashill’s medications needs to up the dosage.”

The most fearsome or the most disturbed journalist in America — take your pick — arrives at a Plaza café on a day ripe for conspiracy theories. The previous night, President Barack Obama announced that U.S. forces had killed Osama bin Laden in northern Pakistan. Commenters on the websites that publish Cashill and discuss his work have already begun to question the official version of events. Cashill worried about al-Qaida’s response as he waited for the president to make his televised address.

“In that 30-minute lead-up to the announcement, I thought there was a nuclear bomb in New York City and that the country was going to blow up,” he says. “I had spent half an hour imagining the worst.”

Hustling assignments and making a living as a freelance writer requires charm, and Cashill has it. He isn’t the least confrontational, despite talking to a reporter who works at a publication that has described Cashill as a “crackpot” and an “intellectual clown shoe.” He asks after his would-be profiler’s life in a way that reflects genuine interest, but it’s curdled by a certain smugness that’s a hazard for chess prodigies, high-functioning alcoholics and others who think they’re smart enough to stay three steps ahead.

Cashill’s first book to question the government line was published in 2003. First Strike: TWA Flight 800 and the Attack on America (co-written with James Sanders) posited that the U.S. military accidentally shot down a passenger jet that exploded off the coast of Long Island in 1996; the intended target of the Navy missile was a plane piloted by terrorists. The story that the public was fed — mechanical failure — was in reality a cover-up by then-President Bill Clinton to ensure the “scandal” wouldn’t hurt his re-election chances.

Cashill followed it with six more books on the liberal plots to lie to Americans, punish conservatives and remake the country as a socialist prison. His latest release, Deconstructing Obama: The Life, Loves, and Letters of America’s First Postmodern President, has sold 20,000 copies and is on track to become his biggest seller yet.

“I think we’ll probably get another sales bump when the re-election campaign starts, and after that I think we’ll have gone as far as we can go with it,” Cashill says. “But I’m very happy with the response. People want to know the true story about this guy.”

More than any of his other works, Deconstructing Obama has connected Cashill to the zeitgeist. Researchers working for Donald Trump solicited input from Cashill when the reality-television boss was threatening a run for president and was indulging birther fantasies. In March, Cashill appeared on the Fox News morning show Fox & Friends.

This is the theory that has elevated him to national news programs and to tea partiers’ nightstands: Obama did not write the books that helped establish him as a brand on a par with Coca-Cola or Playboy. Cashill believes that the author of Obama’s acclaimed 1995 memoir, Dreams From My Father, was actually Bill Ayers, the former Weather Underground leader whose association with Obama became an issue during the 2008 presidential campaign.

Cashill’s evidence is a tangle of anonymous informants, personal theories on creative writing, and metaphors repeated in both Obama’s and Ayers’ prose. The assembled coincidences can be a potent enticement down the rabbit hole. There’s no smoking gun, but Cashill is convinced.


“Barring a deathbed confession, yeah, it’s hard to know,” he concedes. “There are people who argue Shakespeare didn’t write all of Shakespeare’s stuff. Except my evidence is hugely better than theirs is. I am 100 percent confident I’m right, and if I am right, it’s the most consequential literary fraud since Profiles in Courage.”

When Deconstructing Obama was released in February, Cashill’s friends told him to expect a Pulitzer Prize. He knew better. None of his books, he points out, have been reviewed in major publications.

“So the story sits there, and it’s like I dropped a frog in the Kool-Aid,” he says. “And no one wants to drink it anymore or talk about the frog in the Kool-Aid or whether it’s a legitimate frog.”

Perhaps unsurprisingly, the hero of Deconstructing Obama is Cashill himself. His literary avatar inhabits an Orwellian world. He runs through a busy airport with a giant head of James Carville following him on televisions tuned to CNN. The few people who can see the truth die before their stories can reach the public. In this world, Obama is being forced on people who lack the intellect to defend themselves from the media onslaught, and the candidate’s public persona is built entirely on the reputation of his memoir.

But the conspiracy doesn’t succeed because Cashill wanders into a bookshop and purchases a paperback edition of Dreams From My Father before he boards a flight to Buffalo.

He begins his quest to disprove Obama’s authorship by sending baiting e-mails to suspected collaborators in the hopes that they’ll confess. (They don’t.) A potential link to Ayers emerges during Cashill’s reading of Fugitive Days, a memoir that Ayers released in 2001. Cashill notes the similarities between it and Dreams From My Father, including the use of nautical imagery and the word “midafternoon.” The aha moments often take place in Cashill’s study as he pores over the prose or exchanges e-mails with friends who have their own suspicions about Obama.

Cashill’s literary detective work began with the idea that Obama did not have the capacity to craft the prose in Dreams From My Father. “Although the book lacks discipline and occasionally grinds on in useless detail, long stretches of Dreams are very well written,” he writes in the first chapter of Deconstructing Obama. Cashill argues that Obama, a lawyer by training, did not have the writing experience to craft an exceptional piece of nonfiction.

Cashill acknowledges that it’s common for authors with political aspirations to work with ghostwriters. That revelation on its own would hardly be a bombshell. Lucky for Cashill the conspiracy theorist, Obama didn’t get just anyone to help him — he got, in Cashill’s view, a terrorist bordering on a supervillain.

“It doesn’t matter if people use ghostwriters,” Cashill says. “I’m not saying some ghostwriter wrote Dreams From My Father. I’m saying the Rosenbergs or Tim McVeigh wrote Dreams From My Father.”

Ayers issued a blunt dismissal of Cashill’s theory in 2009. “You’ve all lost your minds,” he wrote in an e-mail to the Daily Beast. “Best of luck in the twilight zone.”

Cashill’s claim that Obama was incapable of producing a decent book opened him up to charges of racism. Cashill says he can’t understand how anyone could see racism in his ideas.

At the same time, Cashill is not oblivious to the politics of race. He notes, for instance, that liberals call Supreme Court Justice Clarence Thomas an intellectual lightweight.

“Well, there’s a racial element to the Thomas thing,” he says. “There’s a racial element because he’s black. But the charge of racism only goes one way, used against the right. It’s totally political.”


In any case, Cashill argues, Obama is immune to racism by virtue of his upbringing, which took place mostly in multiethnic Hawaii.

“The irony is, Clarence Thomas grew up about as black as you can grow up,” Cashill says. “Raised by his grandfather who was a sharecropper, no indoor plumbing, all that stuff in the Jim Crow South. Obama, culturally, he’s no blacker than you or I am.”

Cashill, 63, grew up in Newark, New Jersey, in what he describes as a typical Irish-Catholic family. Poker games, horse races and the bottle were as much a part of their lives as Sunday Mass. His father, William Cashill, was a police detective who every day walked in suit and tie to the police station, at the end of their block.

Later, Cashill’s father was made to work as a patrolman at a station across town. Blame for the demotion fell on ethnic rivalries within the police force. Forced to work nights in uniform, Cashill’s father became sullen at home.

“He killed himself when I was 15,” Cashill says. “It was the same year Kennedy died. They both died the same way, bullet to the head.”

His father’s experience hardened Cashill to political realities. “Yeah, I probably saw things a little differently than people who hadn’t gotten that close to it,” he says. “That was Newark. The guy who gave me my Eagle Scout badge died in prison.”

Though he came from a cop family, Cashill decided not to pursue a career in law enforcement. “My mother would’ve killed me,” he says.

Instead, he became a scholar. In 1982, he received a doctorate in American studies at Purdue University, where he met his wife, Joan FitzPatrick Dean. She accepted a job teaching English at the University of Missouri–Kansas City a year after they graduated.

Cashill, unsure about his direction in life, went to work for the Housing Authority of Kansas City, Missouri. He hated it. The bureaucracy was slow and, he decided, corrupt. “We [the staff] actually staged a walkout at one point because we didn’t want to just take it,” Cashill says. “You know how The Kansas City Star covered it? ‘Three-Ring Circus at Housing Authority.’ Just no attention paid at all.”

It was around this time that he met R. Crosby Kemper III, the scion of the banking family and a lifelong conservative.

“He was still coming out of his liberal phase when I met him,” Kemper says. “You know that quote, ‘If you’re in your 20s and you vote Republican, you don’t have a heart. But if you’re in you’re 40s and you don’t vote Republican, you don’t have a brain?’ It was that sort of thing, but Jack didn’t need until his 40s to catch on.”

Cashill and Kemper shared an interest in American literature. They talked about the scarcity of novels with businessmen as heroes and guessed that it had something to do with the prevalence of left-wing types in the arts.

Kemper says Cashill liked to argue, and he was good at it.

“One thing about Jack is that he’s very calm,” Kemper says. “I remember having a dinner at my house, and Jack was there, and there was also another friend of mine who’s liberal. They got into a debate about abortion — Jack’s pro-life. My friend who was a liberal just kept getting angrier and angrier as the debate went on, but Cashill just sat there totally cool and collected and just destroying the guy’s arguments.”


Cashill began to make a name for himself in his adopted hometown. He hosted a talk-radio show and became a columnist at Ingram’s, the monthly business magazine. Writing at Ingram’s, Cashill rapped knuckles but kept ideology largely out of it. His conservatism was more evident in the occasional essays he sold to The Wall Street Journal and The Weekly Standard.

Then, in the mid-1990s, while editing a series of programs for public television in Kansas City, he came up with the idea of making a documentary on TWA flight 800.

“I was at a dinner party once with a guy who was in the military, and it came up, and he says to me, ‘I can get you the serial number of the missile that shot it down. I can’t say who fired it, though,'” Cashill recalls.

Cashill says he wouldn’t have attempted to write such a book in an age before search engines. “Before the Internet came along, are you kidding? I could never be an investigative journalist. Once that was at your fingertips, you could find any expert you needed.”

First Strike made Cashill a minor star on conservative websites. But the editors at established publications in New York and Washington suddenly lost interest in him.

“Once I started writing about what happened to Flight TWA, that was the end of it,” Cashill says. “The Wall Street Journal and The Weekly Standard never returned my calls again. That’s fine. I can write for those publications or I can cover the biggest stories of our time and still make $100,000 a year. I don’t need to have my name in The Wall Street Journal.”

Still, Cashill seems bothered by the loss of prestige. The Deconstructing Obama book jacket omits that the author lives in the
Midwest and that his work is most often featured on partisan websites. Instead, his fleeting appearances in the pages of The Washington Post and The Wall Street Journal receive mention. In the author photo, he’s standing in front of the Golden Gate Bridge.

Two years before the Simon & Schuster imprint Threshold Editions released Deconstructing Obama, Cashill used the far-right website World Net Daily to mull over his theories about Obama’s writings.

World Net Daily was founded by Joseph Farah, who edited newspapers in California before launching the site in 1997. One of the site’s most popular columnists is action star Chuck Norris. In recent years, the site has become infamous for catering to the birther movement.

Farah met Cashill through mutual friends. “There’s an intellectualism in Jack’s work that appeals to, I think, people who are thinkers,” Farah tells The Pitch. “The insights you get from reading Cashill are unlike any you can get from reading anyone else. I think that’s what makes him so special.”

Though his background is in newspapers, Farah admits that his columnists do not always practice standard journalism.

“I get in trouble when I say this, but we have columnists across the political spectrum, and columnists have a certain leeway,” he says. “They’re trying to make a point, and certainly we hope and pray they’ll use facts to make their point, but sometimes they don’t. Sometimes they bend the rules quite a bit.”

The flexible standards at World Net Daily were evident in April, when Cashill attempted to report on the “discovery” that a well-known photograph of a college-age Obama and his grandparents was a forgery.

Working with images that he received from an amateur sleuth, Cashill claimed that Obama had been digitally inserted into a picture of his grandparents sitting on a park bench. But the supposedly original photo of the grandparents was clearly a bad Photoshop job. Obama’s right knee was still visible in the picture that Cashill had deemed authentic.


Cashill’s column on the site was live for only hours before Media Matters for America, a liberal watchdog group, drew attention to the floating knee and mocked Cashill’s detective skills.

“I was absolutely crushed when that happened,” Cashill says. “I felt very foolish. But I’d say that in all the years I’ve been reporting, there’s never been an error like that before.”

The images and any references to it were immediately scrubbed from Cashill’s column. World Net Daily readers who visited the site later that morning were told nothing of the error. Cashill says he can’t say for sure how the changes were made.

Farah says he, too, is at a loss. “I wish I could tell you what happened there, I really do,” he says. “I’m the editor and CEO. That’s not a copout, but I’ll be very honest with you. I don’t have time to read all the commentary on WND after it’s published, let alone before it’s published. We honestly don’t follow the back and forth all that much.”

Cashill has a history of working across party lines. He advised Claire McCaskill when the U.S. senator served in the Missouri House of Representatives in the 1980s. Former Kansas City Mayor Mark Funkhouser added Cashill to his kitchen cabinet midway through his term. At the time, Funkhouser was dealing with criticism and lawsuits stemming from his decision to allow his wife, Gloria Squitiro, to function as a sort of co-mayor.

Funkhouser identified himself as a liberal Democrat. “At first, I thought we wouldn’t get along and that our political differences would be too great to work together,” Squitiro tells The Pitch.

Cashill proved to be an affable adviser who didn’t push his conservative views. He gave the Funkhousers two suggestions. First, he wanted Squitiro to raise her visibility. He felt that if she spoke out, the city would see her as something different from the crass, unbalanced, woman depicted in the media.

The second piece of advice was even more unconventional. Cashill encouraged Funkhouser and Squitiro to attend random weddings around Kansas City.

“Not every single wedding,” Cashill says. “They’d call the couples and ask permission, and the ones that accepted them, they’d come. It’d be great for them because it’d show people how committed they were to marriage. So many of the problems we have are because of broken homes, and people would’ve loved it.”

Neither of Cashill’s suggestions was adopted.

“I’m not sure about the weddings, but I do think he was right about getting me in front of the cameras more,” Squitiro says. “I wish we’d done that. If we’d done that, I really think we would’ve been re-elected.”

Cashill is consistently contrary. Rather than get his morning coffee at Starbucks or any of the other coffee shops around the city, he starts most days at Panache Chocolatier, a specialty sweet shop on the Plaza.

He likes to enjoy his coffee at one of the tables placed outside the store. He’s there often enough that he’s a familiar face. The UPS man stops to ask him about a column he wrote, shaking his head at the things that Cashill has uncovered. Cashill smiles, sips his drink and smooths down his gray comb-over before the wind scatters it.

Despite everything else he has questioned, Cashill has always accepted that Obama was born in the United States. But now that the long-form birth certificate has been released, he’s not so sure. Some sleuthing might be in store.


Cashill insists that his research process is a cautious one. He says he vets the experts he finds on the Internet.

“When I was working on the TWA book, I met a mechanic who told me he had absolute evidence. And he completely believed it. So while he was telling me about it I thought, ‘Well, maybe this is something.’ Then it turned out he was absolutely wrong about everything and couldn’t back up his statements. So, of course, I didn’t pursue that line.

“The most dangerous people are the ones who are sincere and are truly convinced of what they’re saying.”

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