How Democrats can beat Trump in 2020: data science and fighting dirty

Few people have given Democratic campaigns more headaches than renegade GOP strategist Rick Wilson. But today, Wilson’s main cause is saving the Republican Party from Trumpism.

How Democrats can beat Trump in 2020: data science and fighting dirty
Rick Wilson on stage during the 2019 Fast Company Innovation Festival [Photo: Celine Grouard for Fast Company]

My interview with Republican media strategist Rick Wilson came under somewhat ironic circumstances at the Fast Company Innovation Festival last week in New York City. While we sat discussing the meltdown of American democratic standards in the Trump Age upstairs from the festival’s main stage, people had sealed off the building for a security check before the appearance of Trump’s friend and supporter Kanye West. West would say during the appearance that he may run for president in 2024.


It is exactly this kind of statement that Wilson now uses his influence to fight against—though that wasn’t always the case. Wilson is best known for creating GOP TV ads that bedeviled opposing Democratic campaigns, such as the controversial 2008 spot featuring disturbing soundbites from the sermons of Barack Obama’s pastor, Jeremiah Wright. But these days, Wilson is a public speaker, author, and Twitter celebrity who frequently speaks out against Trump’s brand of politics.

I spoke to him about lies in political ads, data science, the GOP after Trump, the economy’s impact on 2020, and the follow-up to his bestselling Everything Trump Touches Dies, called Running with the Devil, which is due out in January.

The following interview has been edited for clarity and brevity.

Fast Company: [Trump campaign manager] Brad Parscale is running Facebook ads saying untrue things, like the Democrats want open borders. He’s going to keep doing that because Facebook said it won’t check the facts in political ads. Is Facebook doing the right thing here?

Rick Wilson: It just boggles my mind. I spent 30 years making television ads for candidates, super PACS, and associations, and for the state and national parties. I had to tell the truth in those ads. The FEC [Federal Election Commission] says if the ad’s fake you can go to the [television] station and go, “This is a false and defamatory ad—take it down,” and they’ll take it down. Not every time. Sometimes there’s an edge on it. Sometimes there’s a little bit of gray area, but for the most part you operate under a set of rules. They can put things on Facebook basically saying, Democrat candidate X wants to have drag queen story hour at the local mandatory Sharia training center, and scare the crap out of people.

Look, I’m a free speech guy, but this is also a corporate platform where there is some responsibility. They’re not guarantors of the First Amendment. And they certainly exercise their corporate discretion on all kinds of things they dislike. You can’t run an ad for gun parts on Facebook. But you can say Bernie Sanders eats babies.


You can’t run an ad for gun parts on Facebook. But you can say Bernie Sanders eats babies.”

FC: If that kind of provocative and fact-challenged advertising works on Facebook, and it does seem to work, why shouldn’t the Democrats do the same thing against Trump? Do they have the stomach for it?

RW: Democrats are holistically bad at politics. They don’t know how to fight in the way Republicans do. And part of it was they were a majority for so many decades. They had all this power and Republicans, we had to come up hard. We had to fight and scrap for everything. Democrats are still in that [power] position, and I don’t understand it. They have a majority of the House, but they’re up against people who are fucking killers. For the most part, this is a business where you lie, cheat, steal, and go all the way up to the legal limit on all these things. If the Democratic side thinks that anybody in Trump World will hesitate to pull a punch on anything, they’re out of their minds.

FC: Let’s say that Biden is the nominee in 2020. Do you think that he’s going to hire data science and digital people who are ready to fight on those terms?

RW: If he doesn’t, it will be the worst political malpractice in history, because all those tools are out there. There is no reason why the Democrats can’t pick this up. And every person in Silicon Valley would beat down their doors and send their best data scientists, their best engineers, and they would be on deck in a hot minute. They just have to ask. And unfortunately, there are people who still believe that yard signs win campaigns. It’s an ugly reality, but it’s an existential threat to them if they don’t have an A-tier data science operation.

FC: What would happen if you personally got that call next year, to go and work for the [Democratic] nominee?

RW: It depends on who the nominee is. Bernie Sanders is not viable. I wouldn’t go to work for somebody who was going to lose 44 states. But if it was Biden, maybe. But look, my position on Trump is abundantly clear. I do not have to agree with the Democratic candidates, philosophies, policies, or anything else to recognize that all the probable nominees in that field are progressive and liberal. But they are also fundamentally from the same basic American strain of politics where we have a back and forth, where we have a homeostasis in our political tensions, where both sides deal with each other.


I do not believe that is the case with Trump. I believe he is an existential threat to the country. And I believe in the Republic before I believe in the Republican Party. So I wouldn’t walk away from the challenge if the time came. I’m not looking for a job right now. I’m not pitching my services. And I think there would be a lot of pushback anyway. Because you know, one of the reasons I have some credibility in this whole discussion is that I was a central figure in the demonology of the Republican Party for a long time. I was a bad guy. I mean, I was the devil. I was the guy bringing in these horrible ads.

FC: What is the future of the Republican Party after Donald Trump?

Unfortunately, there are people who still believe that yard signs win campaigns.”

RW: I think that Republicans are going to deeply, fundamentally, and profoundly regret the way that they have—the way Trump has—framed the party with Hispanics. I was born in Florida. My first political campaign was as a field director for George Herbert Walker Bush in 1988. Even then, there was a high-order effort to communicate with Hispanic voters.

I think Trump is so dangerous because the people that he appeals to the most have this sense of despair and oppression that has become a central defining characteristic of their lives. And they feel like only he is their avatar; only he will fight for them; only he will keep the wolf from the proverbial door.

FC: When I talk to these people in my home state who are very, very loyal to Trump, it makes me wonder if there’s anything that could be said, any kind of messaging, that might turn some of them away from Trump.

RW: Some of them [might turn away] on the economic heartbreak side. Some of them on the broken-promises side. You know, he said he would do X, [and] he did not. He claims there are 150 new steel plants—there are none. There was one that was planned back under Obama. He claimed that we’re going to add a half-million coal jobs—they’ve added like 400. I think some of that could break, especially if the economy takes a dive.


But I don’t think the economy is going to take a dive. I think the stock market is perversely incentivized to keep Trump there because his tweeting allows algorithmically based trading. Trump puts out a tweet that says we have a trade deal with China and software sees it—no human eye has to touch it—and the market bumps up 10% to 15%. These guys make a ton of money on the delta. I think they are perversely incentivized to keep the economy bubbling along.

FC: We hear a lot about Trump’s connection with fundamentalists and the religious right? Is there anything that might break them away?

I don’t think the base will ever accept anything other than a clown.”

RW: They all love them some Donald. I don’t think there’s anything that breaks the evangelical cohort off again. Modern evangelical Christianity exists in a perceived bubble of oppression and threat that the culture and other religions are all seeking to destroy them. And so they’re willing to make any compromise to prevent that destruction, even though it’s imaginary.

It’s like me saying, “I’m afraid of being gored by a unicorn.” I’m not going to be gored by a unicorn. But if somebody came to me and said, “Oh, I know you’re afraid of unicorns; I’m going to kill all the unicorns,” I’d go, “Okay!” But [they’d say], “You have to forgive me for being a unicorn killer and also for being a guy who [has sex with] porn stars and all this other stuff.” They forgive him for all that stuff because he’s their avatar.

FC: Can they even forgive him for being a toady to Putin?

RW: Yeah, I think they have. I think they’ve already forgiven it. I don’t think they care. One of the things that led guys like [Steve] Bannon and [Sebastian] Gorka and all these other people to a sort of pro-Russian stance is the perception that Vladimir Putin was part of the Christian West. And they believe that he’s an anti-Muslim and that he’s pro-white-birth and all these other things. I think that’s where that bizarre fetish for Putin emerged.


FC: After everything that’s happened since your first book, Everything Trump Touches Dies, what is the worldview of this next book? How is it different?

RW: My worldview is honestly a little darker because I was still talking to Republicans when I wrote the first book. People would call me up and say, “Oh my God, he’s horrible. What are we doing? He’s destroying our country. He’s destroying our party.”

Those guys are all gone now. They either quit or were beaten. There’s a couple left. But they all live in absolute fear. And every single one of them, including the ones you think love him, every one of them hates him. Ted Cruz, Marco Rubio, even Josh Hawley—they hate him. Really. They cannot believe that this guy is president and they are not.

But they’re all trying to define this vision of a post-Trump Republican Party that keeps all the aspects of political Trumpism, without being Trumpish. I don’t think it’s possible. And I don’t think the base will ever accept anything other than a clown. A showman. A jackass like Trump, from now on. That’s scary. That’s pretty scary.