Dinesh D’Souza’s Life After Conviction

It was seven P.M., and Dinesh D’Souza—political pundit, writer, documentary-film maker, and onetime wunderkind of the intellectual elite—was dining in his new haunt: the Subway sandwich shop in National City, San Diego, a downtrodden Latino neighborhood about 20 miles from the Mexican border. He ordered his usual: six-inch whole-wheat sub with tuna salad and provolone. The girl making it was one step ahead of him. “He’s one of my randoms,” she said affectionately. Indeed, in his glasses, striped sweater over a polo shirt, and clean sneakers, D’Souza looked as if he were heading for a start-up rollout event instead of a community confinement center a few minutes away, where he is serving an eight-month sentence during nighttime hours.

The rest of his evening would look something like this: He would check in to the confinement center at 7:57 P.M., three minutes before his 8 P.M. curfew. Certain that the Obama administration is waiting for him to slip up, he wouldn’t risk being late, which is why he eats near the facility and not at his home, 20 miles away in La Jolla, where he is free to spend the day (though he may not leave the confines of San Diego County). Upon entering the center’s fluorescent-lit, low-ceilinged building, situated across from a pungent recycling dump, he would be given a Breathalyzer test and patted down. He would join about 90 other residents, mostly Latino. After using one of the stalls of his communal bathroom, he would enter the open-plan sleeping quarters and climb onto a top bunk, above a 400-pound guy who, “when he moves, the whole bunk bed shakes.” He would do his best to focus on his book and to block out the conversation. “I’ll be on my bed. I’ll hear four guys discussing the tits on the woman at Los Tacos. It will go on and on and on. I’m just powerless to move.”

D’Souza reports on his new living situation with high energy and a matter-of-fact bemusement punctuated by an eager, slightly dorky laugh—which is odd, given his grim circumstances. Last May, he pleaded guilty to a campaign-finance violation after he was caught getting two straw donors to contribute to the campaign of his old friend Wendy Long, who was running against Kirsten Gillibrand in the U.S. Senate race in New York. At one point, he was facing up to two years in prison, though he ultimately got eight months in a halfway house, plus community service, and a $30,000 fine. Still, it’s no small price to pay given that most people who commit the same crime don’t get caught. So, why is he so animated? According to D’Souza, there’s a conspiracy afoot: he’s a victim of Obama’s anti-colonialist rage.

It makes perfect sense, right? In the past five years, he has turned Obama’s alleged rage into a fortune with three books—The Roots of Obama’s Rage, Obama’s America, and *America: Imagine a World Without Her—*and companion documentaries for the last two, one of which grossed $33 million, making it the highest-grossing political documentary after Michael Moore’s Fahrenheit 9/11.

__Watch: A Rare Glimpse Inside Dinesh D’Souza’s Life After Conviction __

After the charges came down in January 2014, he cried “selective prosecution,” a serious offense in which the government unfairly targets an individual—in this case, for political retribution. Alas, D’Souza didn’t have evidence that the president, or Attorney General Eric Holder, or anyone else in the Justice Department, was out to get him. When he couldn’t get the case thrown out on that basis, he pleaded guilty and claimed to take responsibility for his actions. The act might have earned him points with the judge, who had the discretion to ignore the sentencing guidelines (from 10 to 16 months of incarceration), but D’Souza seemed to squander the judge’s goodwill by publicly and repeatedly announcing that he was a victim of political persecution. The judge seemed perplexed. Why was D’Souza engaging in self-sabotage? Did he have some kind of psychological affliction? Why, in the first place, did a man who had achieved so much success so carelessly flout the law when there was so little to gain? In short, how could such a smart man be so stupid?

Indeed, D’Souza may be the most maddening, bewildering figure in the punditry world. He is eminently likable in person: courteous, avuncular, chatty, quick to laugh, and willing to lay himself open to ridicule. He’s also a doting father to an intelligent, polite 20-year-old daughter, who utterly reveres him. But in his public life he’s pathologically drawn to pushing the bounds of civil discourse, often with a disinterest in backing up his assertions with facts. While this approach has won him hundreds of thousands of fans of the Joe the Plumber variety, it has eaten away at his respectability in intellectual circles. Few members of the media elite, he complains, have been willing to publicly defend him.

Immigrant Narrative

Even as a kid, D’Souza demonstrated versions of these two sides—the hopeful immigrant, determined to excel, and the attention-seeking pest. One of his aspirations as a middle-class boy growing up in Mumbai was to memorize the entire English dictionary. Through a Rotary exchange program he ended up, at age 17, in a small town in Arizona. After “crushing the S.A.T.’s,” he landed at Dartmouth. The ways of the Northeast elite were totally alien to him, but he quickly found a group of students that would become his “surrogate family” and unleash his inner frat-boy knucklehead. With support from a charismatic professor, Jeffrey Hart, who was a senior editor at William F. Buckley Jr.’s The National Review, the group founded The Dartmouth Review, with the aim of challenging in the most offensive ways possible what they saw as liberal campus claptrap. Under D’Souza’s editorship, the paper published a “lighthearted interview” with a former member of the Ku Klux Klan, accompanied by a staged photo of a black man hanging from a tree; an article about affirmative action entitled “Dis Sho’ Ain’t No Jive, Bro,” written in Ebonics; and the names of members of the Gay Student Alliance. In his memoir, Stress Test, former Treasury secretary Tim Geithner, who attended Dartmouth at the same time as D’Souza, recalls running into him at a coffee shop and asking him “how it felt to be such a dick.”

D’Souza allows that some of his behavior may have been “sophomoric.” But, as the leader of the young conservative counter-Establishment, he got national attention. “Here I am. I’m 20 years old, 21, and I find myself being written about in The New York Times and Newsweek,” D’Souza recalls. Soon after graduation, he parlayed his young fame into a stint as managing editor of a right-wing quarterly, Policy Review, before landing a job in the Reagan White House as a domestic-policy analyst. Seeing a career in government as a slog, in 1989 he accepted a job offer from the American Enterprise Institute, the pre-eminent conservative think tank.

He could easily have spent the next couple of years churning out dry policy pieces. Indeed, his first few books went nowhere. But in 1991, his Illiberal Education was a smash hit: an exhaustively researched takedown of the political correctness that was sweeping college campuses and that he believed was undermining academic standards and chilling freedom of thought. His editor, Adam Bellow (son of novelist Saul Bellow), had urged D’Souza to aim to engage even liberals, and D’Souza did just that. The book put on the map a conversation that was necessary at the time, and it became a best-seller, getting rave reviews and prominent cover placement in The Atlantic, The New York Review of Books, and The New Republic. “Illiberal Education was terrific,” recalls Andrew Sullivan, then the editor of The New Republic. “He had a sharp intellect and a gift for provocation, in a good way.”

“Suddenly, I just became a huge mainstream celebrity in the intellectual world,” says D’Souza, who was inundated with speaking invitations. He also became a hot commodity among blonde conservatives. After dating Laura Ingraham and then Ann Coulter, he found the ultimate prize in Dixie Brubaker, a beautiful blonde from a conservative California family, whom he had met while working in the White House; they married in 1992. D’Souza admits, “It was my mission to marry the all-American girl.”

He had the plum job, the perfect wife, and a provocative tack that seemed to work. Emboldened by the success of Illiberal Education, he pushed his argument further, in 1995, with The End of Racism. His being brown himself, he believed, put him in a privileged position to comment on race and would inoculate him against criticism. Among his assertions: slavery in this country was not actually based on race. That if we’re going to discuss America owing blacks reparations for slavery, then what do blacks owe America for the abolition of slavery? He riffed on “widely different personalities” developed during slavery—“the playful Sambo, the sullen ‘field nigger,’ the dependable Mammy, the sly and inscrutable trickster”—that, he claimed, were “still recognizable.” It was another best-seller, but this time the press denounced it as insensitive. Sullivan, who had planned to run an excerpt in The New Republic, declined to publish it. Eventually, recalls Sullivan, “in the office, he was called by his nickname, ‘Distort Denewsa.’ ” Glenn Loury and Bob Woodson, two African-American colleagues at A.E.I., resigned in protest. As Loury wrote, “It violated the canons of civility and commonality.”

But, D’Souza says, “I didn’t believe that sensitivity had a legitimate place in the debate. Sensitivity was the reason why the debate had the artificiality it did. Everyone has to walk on eggshells…. And I’m like, ‘I’m not going to do that…. I didn’t do any of this to you. So I don’t owe you anything.’ ” He ditched Washington for his wife’s hometown of San Diego and got a job at the Hoover Institution, Stanford’s conservative think tank.

After making wild arguments about race, he would make even wilder arguments about 9/11, in the 2007 book The Enemy at Home: The Cultural Left and Its Responsibility for 9/11—whose title summed up its thesis. The real reason terrorists destroyed the Twin Towers, he wrote, was anger stirred by the left—Hillary Clinton, Nancy Pelosi, Planned Parenthood, Brokeback Mountain, and The Vagina Monologues. He placed special blame on divorce and adultery, inventions, he wrote, of the left. The logic was as tortuous as it needed to be: the Abu Ghraib scandal, for example, was actually the fault of liberals because the soldiers who enacted the despicable acts, Lynddie England and Charles Graner, were divorced, sex-crazed partiers who were therefore “act[ing] out the fantasies of blue America.” As a remedy to terrorism, he advocated that God-fearing right-wing Americans should join forces with their natural ally, traditional Muslims, including those who agree with Sharia law. Many right-wing critics, including some at the Hoover Institution, hadn’t encountered such creative hypothesizing, and they were nearly unanimous in their appraisal—calling his arguments “dishonest,” “intellectually obtuse,” and “suicidal.”

He recognizes that he may have gone overboard with his thesis. “Look, I may be wrong about it,” he says today. “I am attracted to arguments that have a certain plausible originality to them.” But he ascribes the criticism coming from his Hoover colleagues to jealousy. “There was a simmering resentment against me at Hoover,” he says. “They all sit around and have coffee once a week. I live in San Diego. I’m not at Hoover. And so they have these very chic events, and I literally parachute in. I’m the celebrity over there. And then I parachute out and I’m gone.” Whether it was their resentment over his stardom or simply that they hated the book, the rift was untenable, and he resigned. His intellectual allies were dwindling.

On a Wing and a Prayer

But as that world appeared to be closing on D’Souza, another, larger world was opening to him. D’Souza’s other beat had been Christianity (with such books as What’s So Great About Christianity and Life After Death), and he eventually gained entrée to the mega-church speaking circuit. In venues such as Rick Warren’s Saddleback Church, in Orange County, which claims to have more than 20,000 congregants, D’Souza says he was selling 800 books in a day. He’d never encountered the American masses before, but they seemed to love him.

As passionate as these folks were about God, they were as fearful of Barack Obama, who had just taken office. Where did this guy come from? Was he African? Muslim? What was the deal with his name? In The Roots of Obama’s Rage (2010), D’Souza answered those questions for them. Obama was born in Hawaii, he admitted, and he wasn’t, to anyone’s knowledge, Muslim. But he had a single goal: to avenge the injustices inflicted by colonialism upon his father’s Kenyan homeland, by intentionally weakening America’s economy and power in the world. The book was written in two months, he boasted in the introduction. And with sentences like these, it showed: “The most powerful country in the world is being governed according to the dream of a Luo tribesman of the 1950s—a polygamist who abandoned his wives, drank himself into a stupor, and bounced around on two iron legs … raging against the world for denying him the realization of his anti-colonial ambitions. This philandering, inebriated, African socialist is now setting the nation’s agenda through the reincarnation of his dreams in his son.”

The conservative Weekly Standard called the book “lunacy,” but to thousands of Americans—among them Newt Gingrich—D’Souza’s theory sounded about right; the book was an instant best-seller. But D’Souza knew there were millions more out there who needed to hear this message. “The battlefield is much bigger. To reach that battlefield, you have to go beyond books.” Inspired by the success of Fahrenheit 9/11, D’Souza partnered with Gerald Molen, the right-wing co-producer of Schindler’s List, raised $2.5 million from private individuals, and made the 2012 documentary 2016: Obama’s America. It received a 26 percent score from critics on Rotten Tomatoes, but what did he care? He was a rock star again, this time doing large arenas. He found in his new fans “foot soldiers that are looking for leadership, intellectual leadership, cultural leadership…. Some of them regard me as a hero.”

But in typical Hollywood fashion, just as he was lapping up his newfound glory, the wheels began to come off his private life. Back in 2010, D’Souza had been asked to be president of the King’s College, a small evangelical college in Manhattan. D’Souza wasn’t strictly evangelical—he was raised Catholic—but says he was leaning in that direction. And he had the name recognition King’s was looking for in its quest to raise money. The offer came with a reported seven-figure salary, and he accepted. While he was packing his bags for New York, “I discovered, to my horror, irrefutable evidence that my wife was involved with someone else.” D’Souza says that Dixie had grown bored with his political life and had no interest in repairing their marriage, so he went to New York without her, traumatized. (Dixie says this is “simply untrue…. I signed us up for a marriage-counseling retreat … and attended marriage-counseling sessions.”)

Given his leadership role at a Christian college, he might have handled the situation with as much grace and care as possible. Instead, his old recklessness took hold. In the summer of 2012, before any divorce papers were filed, he began secretly seeing Denise Odie Joseph II, a D’Souza groupie, married and 22 years his junior. She kept a blog called “I, Denise, Lust After … ” on which she called D’Souza “one of our favorite conservative activist philosophers.” He admits, “I was completely blown away.”

It was too dizzying a time to deal with the mundane obligations he’d taken on, like helping to fund-raise for Wendy Long, his old Dartmouth Review compatriot, in her Senate race. The campaign was hopeless, “a joke,” according to D’Souza, and she kept asking him to do tedious tasks, like meeting with groups of wealthy Indian doctors in Westchester to ask for their support. He completely blew it off but was starting to feel guilty.

He’d already reached the legal donation limit by giving $10,000, on behalf of himself and his estranged wife. But there was a lot more needed. So he asked his new lover and her husband to contribute $10,000 and said he’d reimburse them. He asked the same of his young assistant, Tyler Vawser, and Vawser’s wife. Vawser was concerned; according to court documents, D’Souza assured him it was fine. If anyone should ask about it, D’Souza said, Vawser should say that he knew Long and that he supported her candidacy. When Long later asked D’Souza about these unusually large contributions, D’Souza assured her that the individuals had the means. Despite the trail of untruths, D’Souza casts the act as one of generosity of spirit and misguided friendship. “All of my friends supported Wendy Long, but none of them supported her like this. Why? They were too smart to do it.... I felt inwardly that I should do more. I felt an obligation to do more.” Not so obligated, it should be said, that it was worth fund-raising the legal way—like traveling to Westchester to meet with a group of Indian doctors.

D ’Souza felt indestructible, and he was on a roll. Weeks after orchestrating the illegal contributions, he brought Joseph along to a conference in South Carolina. The subject was how to apply a Christian worldview to one’s life, and D’Souza was the keynote speaker. He introduced Joseph as his fiancée to several people, even though both of them were still married to others. Alas, a reporter named Warren Cole Smith from the Christian publication World Magazine discovered that he and Joseph were sharing a room. Six days later, Smith called D’Souza to ask how he could be engaged when he was still married. D’Souza replied that he had filed for divorce “recently.” When Smith checked, it turned out that D’Souza had filed for divorce that very day.

D’Souza maintains that he was the victim of a vendetta: Marvin Olasky, the editor of World Magazine, who had been provost at the King’s College, had fought against D’Souza’s appointment. The reporter, Smith, had been a consultant to the King’s College until D’Souza ended his contract. In addition, says D’Souza, the suggestion that he was committing adultery and lying about it to his employers was disingenuous; he says that he’d already told then King’s College board chairman Andy Mills that his marriage was effectively over before taking the job. Mills, however, disputes D’Souza’s account. “I had no sense that the marriage was over, no sense that he’d separated,” says Mills. “On the contrary, it was, ‘We’re having difficulties, but we’re working on it.’ In fact over the next year, the reports [about their marriage] were quite positive…. So it was a great shock to me when we found out about the ‘separation from his wife’ and this girlfriend. That was completely out of left field.” D’Souza was promptly asked to resign. As for Joseph, “here she is, emblazoned all over the Internet, and people are discussing her breasts…. It put a strain on our relationship,” recalls D’Souza. They broke up soon after. Things were about to get worse.

At some point in 2013, after conducting what the government called a routine review of Long’s campaign filings, the F.B.I. reported to the Justice Department a couple of red flags—two contributions totaling $10,000 each from individuals not known to Long, in a sea of smaller contributions. In January 2014, after investigators questioned Joseph and Vawser, neither of whom were prosecuted, Preet Bharara, the U.S. attorney for the Southern District of New York, charged D’Souza with two counts: violating federal campaign-finance laws and causing a false statement to be made to the Federal Election Commission. The two charges could bring up to seven years’ jail time. D’Souza hired Benjamin Brafman, whose clients have included Michael Jackson and Dominique Strauss-Kahn. For four months D’Souza refused to plead guilty. Instead, Brafman sought to have the charges thrown out on the grounds that D’Souza was the victim of selective prosecution. According to the motion, D’Souza was being targeted because he was “a sharp critic of the Obama presidency who has incurred the president’s wrath.”

To back up this claim, Brafman cited several similar straw-donor cases that were settled by fines, not criminal prosecution. The cases that resulted in jail time, he argued, involved either larger sums of money or larger schemes of corruption. The prosecution countered that D’Souza’s case had distinguishing characteristics that made it egregious enough: he had involved a person in his employ, Vawser, whom he encouraged to lie, and he had repeatedly lied to Long. In the end, U.S. District Court judge Richard M. Berman determined that D’Souza’s claim of selective prosecution was “all hat and no cattle.” The case would not be dismissed.

Jolly Good Felon

On May 20, 2014, the day the trial was to begin, D’Souza pleaded guilty to the illegal campaign contribution charge (taking the second charge off the table) and professed to take responsibility for his actions. The next few months would be critical, as the judge would be deliberating on the appropriate sentence. The moment called for humility. D’Souza enlisted 27 people—colleagues, friends, and family members in India—to write to the judge on his behalf. While they got busy attesting to his remorse, he began publicly conveying just the opposite. Brafman begged his client to keep his mouth shut, but D’Souza couldn’t resist. He was finishing up his second documentary, America: Imagine a World Without Her, which was to be released imminently, and had to insert one last scene: Dinesh himself in handcuffs, rubbing his eyes, accompanied by a treacly voice-over: “I’m not above the law. No one is. But we don’t want to live in a society where Lady Justice has one eye open and winks at her friends, and casts the evil eye at her adversaries. When will it stop?” He repeated a similar line in interviews with Megyn Kelly on Fox and elsewhere. On September 3, as his sentencing day approached, he wrote to the judge that he was “ashamed and contrite.” Two days later, he posted on Twitter: “The Obama campaign to shut me up: is it working?” Although Brafman has come to “grudgingly respect” D’Souza’s decision to speak out, he admits that “Dinesh was trying to do everything possible to alienate the government and the court while I was working my ass off trying to develop arguments to support a very lenient sentence.”

Judge Berman could only wonder. “I’m not sure, Mr. D’Souza, that you get it,” he told him on September 23, the day of the sentencing hearing. “The defense says it has accepted the court’s rulings in this case, yet Mr. D’Souza … continues to deflect and minimize the significance of the crime and of his behavior.” D’Souza’s public pronouncements, he went on, were “totally thoughtless and not self-reflective and not self aware…. I’m totally confident that Lady Justice is doing her job and that she’s not taking off her blindfold to target Dinesh D’Souza.” D’Souza’s trail of bluster had finally caught up with him in court. The judge sentenced him to five years’ probation, a full day of community service each week for those five years, eight months in a confinement center, and therapeutic counseling. A week later, D’Souza reportedly had a request. Could he delay the sentence? Because he really wanted to, among other things, promote his new movie. The judge wrote, “Respectfully denied.”

In October, D’Souza entered the confinement center, joining the kind of people he had publicly referred to as “parasitic.” Luckily, none seemed to be familiar with his work. Those first days had their Orange Is the New Black moments. The first night, he slept “with one eye open.” While he was lying there, his 400-pound bunkmate struck up a conversation: “He goes, ‘Hey, man, what are you in for?’ I go, ‘Campaign-finance violation.’ He goes, ‘What the fuck does that mean?’ I go, ‘Well, my friend was running for the Senate, and I gave her too much money. I raised money for her in the wrong way.’ So he goes, ‘Shit! Can you raise money for me?’ I go, ‘No.’ Then there was the mandatory rape class, which was about ‘establishing that all of us have a right not to be raped.’ Very reassuring.”

But D’Souza also shows flashes of self-reflection. Looking back on the recent events in his life, he says, “Part of what you learn about life is that a wrecking ball can come out of nowhere, and it isn’t just going to take out your left toe. It can hit you right in the middle and take you down.” His personal experience has made him re-assess some of his public stances. His community service, teaching English to Mexican immigrants, some of whom are undocumented, has softened his stance on immigration. He once had a credo that “the quality of the immigrant is directly proportional to the distance traveled to get here.... But I now see that the adults in my class are incredibly industrious, determined, and hardworking, and no less strenuous in their pursuit of the American Dream than any other immigrant group.” Likewise, his own divorce has “sobered and humbled me and made me a lot more tentative about things I was sure about.” It seems he’s no longer convinced that the country’s acceptance of divorce led to the destruction of the World Trade Center. And he is as productive as ever. His future plans include starting a PAC, to pay for getting his America documentary shown on hundreds of campuses, and writing a new book with a companion film about the “secret history” of the left. He is also trying his hand at Christian-themed feature films and, to that end, is busy writing screenplays for a thriller and a family film.

Still, old addictions are hard to break. On Martin Luther King Jr. Day, he tweeted, “An interesting parallel: MLK was targeted by J. Edgar Hoover, an unsavory character. I was targeted by the equally unsavory B. Hussein Obama.” You’d think he’d made his point already. But in his view, it was working—since his sentencing, he says he has raised $10 million toward his new film—so why stop? “This whole episode,” he says, “far from denting my career, has actually brought me to the attention of a wider audience.”