
Dinesh D’Souza (Photo by Imeh Akpanudosen/Getty Images)
Every election season creates new celebrities. Earlier this year I told you about Dilbert creator and political oracle Scott Adams, and today I am going to tell you about political commentator, author and filmmaker Dinesh D’Souza.
(If you’ve heard of D’Souza and want to skip my introduction, and get right to the conversation then by all means scroll down to where our conversation begins.)

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It is hard to be lukewarm on D’Souza — you either love him or think he’s “batshit crazy” (GQ’s words not mine). Even if you haven’t read his books or seen his movies, there is a good chance you’ve come across D’Souza’s influence without even knowing it. For instance, when Donald Trump recently called the Democrats the party of slavery and Jim Crow, it was clear that he had seen D’Souza’s movie Hillary’s America, the top grossing documentary of 2016 which was rereleased in theaters this weekend.
Audiences love it, critics not so much. More on that in a minute.
D’Souza’s movie starts in court where he is being sentenced to eight months in a halfway house for a campaign finance violation, a crime to which D’Souza pleaded guilty. D’Souza believes that he was targeted by the Obama administration for another movie he made, Obama 2016, which would explain why he received an unreasonably harsh sentence for a violation which normally gets a slap on the wrist. D’Souza’s eureka moment comes when he strikes up a conversation with a fellow inmate at the halfway house who tells D’Souza about the elaborate insurance con that landed him in prison. The films then goes through a history of the Democratic party beginning with Andrew Jackson all the way through LBJ showing how the Democrats championed slavery, segregation, and removing Native Americans from their land. D’Souza, who never pretends to be unbiased, thinks the people running the party are, like his fellow inmate, running the biggest con of all. And, as the title would suggest, he sees Hillary as a worthy heir to the throne.
Dinesh is joining me today for a conversation about his movie. He has done many interviews (the best one I’ve seen was with Larry King), but today is his first ReplyAll conversation, so I’m going to try to ask questions I haven’t seen others ask elsewhere. As always, this conversation isn’t a “live chat,” it is a real-life conversation so for the best experience, follow along below.

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Zach Abramowitz is a former Biglaw associate and currently CEO and co-founder of ReplyAll. You can follow Zach on Twitter (@zachabramowitz) or reach him by email at [email protected].