On September 23, Dinesh D’Souza will appear before a federal judge in Manhattan to learn whether he will do jail time for violating campaign-finance law. (He pleaded guilty earlier this year to charges of funneling $20,000 to a friend’s Senate campaign via straw donors.) It will be the latest turn in a remarkable life that has embodied—perhaps more than any other—the passions and commitments of the modern conservative movement.

D’Souza leapt to prominence during his student days as editor of The Dartmouth Review, then emerging as a first-read for pro-Reagan provocation. Those were heady times for the youth corps of the conservative “counter-establishment,” and no star shone more brightly than D’Souza’s. Witty, sharp-tongued, and ingratiating, he was also exotic, a Catholic raised in Mumbai. He seemed on his way to being the next William F. Buckley Jr., an against-the-grain conservative perfectly suited to his multicultural moment. Buckley himself anointed the young writer the future “President D’Souza.” He was only half joking.

D’Souza did work briefly in the Reagan administration, but politics wasn’t his métier. His talent, like Buckley’s, was for attacking the liberal jugular. Where he was once content to do battle on the intellectual circuit, however, D’Souza has increasingly sought to rally— he would say enlighten—the masses. At 53, he now shares stages with Sarah Palin and addresses throngs of “guys who have open shirts and tattoos and wear funny hats and drive bikes of a kind I would never get on.” He has also branched out into filmmaking: 2016: Obama’s America, D’Souza’s first movie, earned more than $33 million, the second-highest box office ever for a political documentary. His second effort, America: Imagine a World Without Her, is just leaving theaters after a successful run.

Yet even as he has expanded his influence, D’Souza has been shadowed by scandal. Along with the campaign-finance case, he lost the presidency of an evangelical college amid allegations of adultery. It is all too tempting to see in this a correlative of intellectual conservatism itself, its dark underside, its extremist gestures.

Or is it, rather, that the self-described “social guerrilla” of Dartmouth in the early ’80s never grew up?  It was one of the many questions I hoped D’Souza might answer when we met for breakfast earlier this month at the boutique midtown Manhattan hotel where he often stays on visits from his home in La Jolla, California.

Sam Tanenhaus: We have to talk about this. You’re about to go back to court for sentencing in your campaign-fraud case. How aware were you that you were breaking the law?

Dinesh D’Souza: Oh, I mean, this is the thing. Wendy Long, the candidate, told me there’s a $10,000 limit per couple. I convincedtwo people to also give her money and I said I would reimburse them.That’s what I did. Had I read the law? No. I certainly didn’t know it was a felony. I mean, I’m not crazy. I knew I was getting around a rule, obviously, otherwise I wouldn’t have reimbursed them. So I did something really stupid. Now, people say, Dinesh, you’re an intelligent man and you’ve been in the political world for twenty-five years. How could you not know? And the answer is: I had never given to a campaign before. Not even to Reagan.

ST: Was Long a Dartmouth friend?

DD: Yeah.

ST: She was running against Kirsten Gillibrand.

DD: It was a quick-slaughter campaign. Wendy had never run for office before. I’ve known her since about 1982. And this is a little bit, I think, the story of the immigrant. In India, I probably had two dozen relatives living in a one-mile radius of my house. When I came to America as a teenager, I was a little bit isolated, and then at Dartmouth, I found an alternative community and who was in it? My conservative pals. They became my surrogate family, and it included Wendy. I’m very close to these people. It’s against that backdrop that these events took place.

I was traveling all around the country promoting 2016. Wendy was imploring me to help: Hey Dinesh, I know these five Indian doctors and I know they’d give me money if you had dinner with them.” I’m like, I don’t want to have dinner with five Indian doctors. Or, “Dinesh, I’m having a fund-raiser, can you be in Westchester?” “No, I can’t—I’m in Tucson.”

I said, look, I need to help this woman. I’ve given the limit. Now, I should have called a lawyer. I could have given to a PAC—there are ten ways to do it. But I took a shortcut. All that being said—all that being said—I should be punished proportionate to the offense, proportionate to what my motives were, which were not corrupt. I wasn’t trying to benefit myself in any way.

ST: Let’s talk a little about your time at Dartmouth. You started college in 1979. You were kind of a literary guy when you got there, right? Didn’t you even want to be a fiction writer at some point?

DD: Yes, that’s all right.

ST: But by the time you graduate, you’re a star writer for The Dartmouth Review and a rising conservative intellectual. You were singled out: Here’s a bright guy who doesn’t fit the stereotype. How conscious of that were you, that they saw you as somebody who was different, and could contribute to this burgeoning movement?

DD: I probably was not fully aware of it. What I was more aware of then was that every year we typically would have—almost by peculiar coincidence—one black kid at The Dartmouth Review. Every year, all of us would apply for an internship to The Wall Street Journal. And inevitably, they would take the black kid. I remember being slightly indignant, thinking, What is this?

ST: Indignant because it seemed like tokenism?

DD: Right. It seemed like a formula. But I think I was simply innocent of the politics of racial representation. For The Wall Street Journal, it was kind of cool to have a young black conservative Ivy League kid on their little team of interns. The Journal guys were conscious of that in a way that I was not.

ST: A piece of the history that I never really knew was the time you spent at Princeton editing a new conservative magazineProspect, I think it was called.

DD: The Princeton guys were impressed by what we had done at The Dartmouth Review. They said, “We can’t find a Princetonian who is sort of like Dinesh.” So they imported me.

ST: This is after you graduated?

DD: It was my first job.

ST: Did they pay you well?

DD: They paid me very poorly. But I had an ulterior motive. I was applying for my green card.

ST: And then you were hired as managing editor at Policy Review. You seemed on track to make it to National Review, like another member of your generation, David Brooks, or Ramesh Ponnuru later.

DD: Right. It was for a time my undergraduate aspiration to be the editor of the National Review. I realized I would be a very implausible Bill Buckley from India.

ST: But you were aware of him as a model.

DD: Everybody was.

ST: Brilliant intellectual, great charm, commands the television waves, is expanding a set of what might seem abstract ideas, realizing that ideological battles are often best expressed as a kind of culture war.

DD: He was witty, he was naughty.

ST: “Social guerrilla” is a phrase you’ve used.

DD: Yeah, he saw that there is a value to iconoclasm and outrage, and he did not hesitate to outrage the other side. Recognizing that it always had to be done in the right way.

ST: Did you ever do it the wrong way, do you think?

DD: I think a couple of times I went over the line. We all did.

ST: What are some of the examples? That piece written in dialect?

DD: Yes, that’s a good example. Keeney Jones got the diabolical idea of writing a defense of affirmative action, but done in a preposterous Ebonics.

ST: There’s a phrase from the past.

DD: It had footnotes. That was his little malicious addendum.

ST: And that was too far?

DD: At the time, I didn’t think so. I thought it was very clever and very witty. Remember, National Lampoon had done a parody of “Archie Bunker” called “All in de Fambly,” written in black jive.

ST: Is that a double standard? Or is there a justifiable reason why it’s OK for them, but not for you?

DD: Well, if a humor magazine that is, you might say, undiscriminating, does it, it’s just another campy, hilarious take on society. It doesn’t have an agenda.

ST: What are some pieces from that time that you are still proud of?

DD: There was one for Policy Review called “The Bishops as Pawns.” The Catholic bishops at the time had written a pastoral letter on the economy and another on nuclear weapons. They were a big part of the debate. I called up about twenty of them and asked them questions like, “What percentage of our budget goes to defense?” Or, “What does the SALT treaty stand for?”

ST: And they didn’t know?

DD: They came across as total fools. The piece was a bit of a cause célèbre on the right, because it was a new type of polemic.

ST: Well, here’s one of the points I wanted to get at. Your first two books were one on Jerry Falwell and an introduction to Catholic thinkers. You were the guy in the think tanks. And then you wrote Illiberal Education, which was on the best-seller list for fifteen weeks. What were you able to do in that book that you didn’t do in the first two?

DD: The first two books I had written literally right out of college—I think the first one I might have started while I was still in school. But then I had gone to Policy Review and then the White House and then AEI. So I had a little more exposure to the intellectual world. And while I was at AEI, I went to lunch with Morton Kondracke. He was part of the Dartmouth old-boys network, so to speak.

ST: And The New Republic in those days!

DD: Yes! I was running all my book ideas by Mort. I had about seven of them.

ST: Do you remember what they were?

DD: I mean, some of them were crazy. I had an idea of doing a dialogue among all the great thinkers—Plato, Aristotle, Mill—as if they were all invited to the same cocktail party. Mort gently but wisely saw that I was getting carried away. Then I started railing about Dartmouth. I said, “We keep telling the alumni what’s going on, and they refuse to believe it.”

ST: This is during the “canon wars” over whether curricula were inclusive enough, the campus shantytowns to protest apartheid investment, etc?

DD: That’s right. And Mort said: “That’s what you should do. Put on your backpack and go to a bunch of campuses. Be a scout, and tell us what’s happening out there.” There, my first big book.

ST: I read somewhere that the conservative editor, Adam Bellow, told you at some point that what you want to do in a book like this is write in a way that liberals have to take seriously. And that book accomplished that.

DD: I wrote it partly to create a schism between liberals and the left, and I was successful in doing that, to a degree. Many prominent liberals defended Illiberal Education, and I think it made a difference in the political-correctness debate.

ST: Your next book, The End of Racism, was really ambitious. It was seven hundred pages. But some liberals criticized it for a lack of empathy. That is, you made a case that society is no longer systematically racist, but still, in those instances where there is discrimination, it wasn’t clear how sympathetic you might be.

DD: I had come to the issue as an outsider. It’s a very different angle from someone who has grown up with Selma and Montgomery and the civil rights movement. So built into that is a certain insensitivity, which is also another word for objectivity.

ST: At what point did you decide or realize that you didn’t want to or didn’t need to operate in the world of book reviews? That rather than write books aimed at the intelligentsia, you could reach audiences much more directly?

DD: Ironically, the answer to that story also relates a little to The New Republic. I was friends with Andrew Sullivan when he was editor of the magazine. I gave him the manuscript of The End of Racism. I remember distinctly, we had lunch together, and Andrew said something like: “You know, you’ve got a very radical idea here. That public discrimination should be prohibited, but private discrimination should be permitted. And that, that is the true principle of a liberal society.” He said he’d been thinking along the same lines about homosexuality. He thought I could make a much bigger argument, and he wanted me to do a piece for the magazine. And I said great.

Andrew called me up a week later, and he said, “Oh, Dinesh, major bloodbath at The New Republic. There’s huge opposition to me doing this.”

ST: And you saw a lesson in that.

DD: I realized that finding common ground with liberals had some natural limits. The argument in The End of Racism went one step too far. I didn’t take the fact that The New Republic rejected my piece as intellectual cowardice. It just showed me how the spectrum plays out.

The other thing was that the culture was shifting. I began to realize that it was much more important to market your own books.

ST: You mean market them yourself?

DD: I picked up that there are two ways to sell books that were much better than book reviews: speaking and media. After Illiberal Education, I just got an avalanche of speaking invitations. For a while, I felt like I was a political candidate. I was speaking every day.

ST: Where?

DD: At campuses for the most part. And then from campuses to civic groups. Women’s Republican clubs all over the country. I realized that I could speak every day—

ST: And get paid for it.

DD: Get paid for it, but also sell a hundred books. Then I realized that there’s radio and television, too. People are interviewing you about your book directly. There’s no intermediary telling the audience whether they like the book or not.

ST: At a certain point, does that alter the way you write?

DD: It can. One of the things I discovered in the late ’90s is there is a large populist conservative audience of people who want to learn. And yet, don’t know. A typical Tea Party member isn’t an intellectual. But he or she has a real affinity with the American founding, a belief that a return to our original principles can save us, and wants to know what those principles are. Not just in crayon outline, but in fleshed-out detail. And I say to myself, I can help that guy, and make a much more valuable contribution than by operating in what I now saw as the very small world of the ambivalent liberal.

ST: Overall, where do you place yourself among David Brooks and David Brock and the rest of your generation of conservative intellectuals who came up in the ’80s? Have you moved further right or have they moved left? Have their views mellowed while your views have sharpened?

DD: There are differences of ... belief. But also of temperament. I don’t write now the way I did when I was twenty, but I am inherently attracted to a certain kind of intellectual originality. I like provocateurs on the left and on the right.

ST: Do you see your style now as being a kind of intentional provocation?

DD: I always have. I’ll never write a book that I don’t think says something original. I’m struggling to find ground that is unoccupied, and I’m kind of surprised and thrilled that there’s so much of it. When I stumbled upon the thesis of The Roots of Obama’s Rage, about Obama being an anti-colonialist, it looked to me like the most obvious thing. Yet when I said it to conservatives, they were both surprised and fearful. They would say, (a) Where’d you get that idea? and (b) Dinesh, why are we talking about Kenya? It sounds like black, black, black. I live in California now, but if I still lived in D.C., those vibes might have terrified me into not writing that book.

ST: You’d have been convinced it would be seen as a racial attack.

DD: Yeah.

ST: You’re saying it’s not?

DD: I’m saying it’s not at all. Actually, the key thing to understand about anti-colonialism is that it has nothing to do with race. It happened to be a Third World movement, but its leaders, with a few exceptions, were nonracial guys. Their point was that the rich countries are essentially looters, and they could have been anybody. The British didn’t come to impose racial domination, they just came to rule. I was moving away from the racial interpretation, saying, look, the key to Obama is not black, it’s historical.

ST: A question about the title of that book. I think fans and critics of Obama will both say, if anything, that his manner can almost seem detached. So why call it rage? Do you actually see an intense anger in Obama? Because it’s not evident to a lot of other people.

DD: Right. But there are two types of rage. Think of it in terms of movies. Look at the rage of Mel Gibson in The Patriot. That’s the rage of the guy who says, This is outrageous and I’m gonna put a stop to it! The other kind of rage is the rage that says nothing. This would be Robert De Niro in Taxi Driver. It pisses you off, but you are stoic. In fact, it would not seem like you’re angry at all.

ST: But De Niro’s not stoic in that movie.

DD: That’s my point. The rage accumulates.

ST: So you think Obama is the Travis Bickle of American politics?

DD: I think with Obama, there is a quiet but nevertheless molten fury that drives him.

ST: How then do we explain his electoral success? He’s the first president since Reagan to be elected to two terms with more than fifty percent of the vote. Is he hoodwinking the public?

DD: This is why there are some people on the conservative side who turn around and say we lost America, the American people are not with us.

ST: Do you say that?

DD: I don’t. The political winds shift and the times change. I don’t see Obamaism as permanent. There are no permanents.

ST: But then why describe Obama in the very strong terms you do, warning that America will become a place we don’t want to live in? Why isn’t he just a skilled guy who comes out of the Democratic Party following an economic collapse and a war that didn’t work? Why this other more alarmed narrative?

DD: Well, I’m completely convinced that Obama is not a normal Democrat. I think if we posed the following question to Bill Clinton, we would already know the answer: Would you like to see America remain as the wealthiest, most successful, and most powerful society in the world for as long as possible? Yes or no? Without asking, I know Bill Clinton’s answer is yes. Incompetent nincompoop that he was, I believe that would be Jimmy Carter’s answer as well. But I don’t think it’s Obama’s answer.

If you put on my sunglasses and you assume not that Obama’s a traitor, not that he’s a secret Muslim, but that he has a view of global justice that requires a shrinking of American power, so that he’s not just a domestic but a global redistributor—you just put on those sunglasses and you look at the world, a lot of what Obama is doing will make complete sense.

ST: How much time have you spent in Hollywood working on the documentaries?

DD: Not much. We had a temporary office in Burbank for the making of America. And we had a premiere in a very cool theater and bowling alley in L.A. That was a first for us. For 2016, we had ignored Hollywood completely. With this film, we were with Lionsgate, and they said, “Let’s do the Hollywood premiere.” We said no. They said, “Yeah, really, let’s. It’ll be cool.” So we did it.

ST: When you say “we,” who are we talking about?

DD: There are about eight of us. We’re a small team. I have a couple other executive producersJerry Molen, who’s my producer and partner in these enterprises.

ST: He produced Schindler’s List.

DD: Jerry is a self-made man. He drove trucks on film lots. Then he became the head of trucking. Then he came to the attention of Steven Spielberg as an associate producer, just basically making sure the trains ran on time. Spielberg liked him and made him producer of a bunch of his films. Jerry’s in his seventies now, but he has come out of retirement to partner with me on these films.

ST: Tell me about Michael Moore as a filmmaker, what you’ve learned from him.

DD: I went back and watched Roger and Me, which I think is his best film. It’s got an interesting premise: General Motors closes down a big auto plant that his dad happened to work at, and he’s going to go find the CEO of General Motors and demand to know why. Now, it fails intellectually, because there is an obvious reason why General Motors might want to close that planti.e., it’s not making money. And one possible reason it’s not making money is General Motors has been paying people like his dad way too much and can make cars much cheaper in North Carolina or other countries. You can’t proceed without confronting that argument. But Michael Moore’s presumption is that the CEO of General Motors, Roger Smith, is just a mean guy who wants to deprive working people of their livelihood. So intellectually, it’s ridiculous. But visually, cinematically, narratively, it works. This clownish Michael Moore showing up everywhere, the cops in dogged pursuit. All of that works. What Michael Moore understands is that a movie traffics in the language of emotion. The intellect is subordinate to that.

ST: And at the very end of your new film, it says, “A D’Souza Entertainment.”

DD: Right.

ST: Will you walk me through what happened at King’s College?

DD: I came to King’s because I liked the idea of King’s. The idea was that Christianity has been in a sort of sectarian environment. Christians speak to other Christians, they write for other Christians. I thought the school’s goal of articulating Christian arguments in secular terms and advancing them in the public square was exactly what our debate needs. Part of what I’d been doing before that was debating atheists on campuses in secular terms. I found those, particularly my debates with [Christopher] Hitchens, just hugely interesting to people.

ST: Did you like him?

DD: Oh yeah. Hitchens and I were pretty close. We’d often put away a bottle of wine together after our debates. We had a fair amount in common and a fair amount to disagree about.

ST: What did you have in common?

DD: First of all, the British English thing. Both of us were more products of Tennyson, Browning, and Jane Austen than we were of Fitzgerald, Hemingway, and Mark Twain. We had a whole education in common.

ST: Back to King’s. You took the position hoping to do big things. Then what happened?

DD: Basically, I was in an unfortunate personal situation. My wife had come to me in the fall of 2010 and essentially told me that she didn’t want to be married to me anymore. I would go back to California and spend time with my daughter, but I was in a separated situation that was known to me and my wife and King’s, but not known publicly. In the summer of 2012, two years later, I met and got involved with another woman. Under ordinary circumstances, that would be something that can happen, but I made the mistake of (a) becoming engaged to her before becoming divorced and (b) taking her to a Christian conference, which I shouldn’t have done.

ST: Are you remarried now?

DD: No.

ST: Afianced?

DD: No, I’m very—I’m single.

ST: So your sentencing, that’s scheduled for September 23.

DD: I go before a judge and he assigns the penalty.

ST: There was a suggestion, maybe it was Sean Hannity who said it, that this was political payback by the Obama administration. Do you think that’s true?

DD: The government said it was the result of a routine review. Apparently, it was a routine review that yielded a single offender—me.

ST: But you don’t have any actual evidence.

DD: Correct.

ST: Is jail a realistic possibility? Does your lawyer think that you will be sentenced actually to serve time?

DD: My lawyers tell me that there is no one in the United States who has received a substantial sentence for doing what I did under similar facts. Hopefully, it will be just community service and a fine, but we don’t know. The judge has guidelines that would allow him to sentence me to up to two years.

ST: So what happens if they send you away? What are you going to do?

DD: I’m just gonna have to go to jail and write something about it.