This week, Ana checked back in with our favorite Never Trumper Rick Wilson. Ana and Rick haven’t talked since February, and a lot has happened in the intervening period. Rick spent a lot of the time working on his book, but hasn’t stopped following the latest developments from the Trump Administration. Their conversation began with a question from Ana about the most important thing that’s happened since they last spoke.

“It is evident that Donald Trump is out of control. That is the biggest story,” Rick said.

Rick also spoke about the way that attacks on the FBI and the rule of law from conservative media and Republican elected officials have bothered him, which led Ana to bring up the about-face that has happened in American politics in the last 18 months: some liberals now love the FBI while conservatives no longer trust it. This led to a longer discussion about the long-term implications of the shift.

“What happens when you have, not just a Democratic president, but a skillful, charismatic president, and aggressive, populist president, who decides that they’re going to apply the exact same principles of executive power that Donald Trump is doing?” Rick hypothesized.

The problems posed to rule of law don’t stop with the FBI, but extend to judgeships, and the administration’s frequent appointments of judges who have endorsements from The Federalist, but are often unqualified and overwhelmingly male.

“I have a corollary to the [William F.] Buckley rule about appointing judges. I want the most qualified, most conservative. I want judges who aren’t gonna be overturned in the lower courts, I want judges who are gonna display solid legal reasoning,” Rick explained.

They also talked about Rick’s upcoming book, “Everything Trump Touches Dies: A Republican Strategist Gets Real About the Worst President Ever.” In it, he not only plans to criticize Trump and the Trump movement, but to also point to a path forward for conservatives who want another way, in part opened by the tax plan and Trump’s desire for a trade war.

“I think there’s a large number of people out there that are gettable that would surprise the Trump advocates. Those people are the folks who legitimately were economic anxiety cases. Because there are people that voted for Trump who really, really looked at the overall economy and the tax system and everything else and said, ‘we’re getting screwed, and no one’s gonna help us, and no one’s gonna save us, and no one’s here for us.’”

Rick and Ana also drew a distinction between people who voted for Trump because of legitimate economic anxieties and the “pointy white hat economic voters.”

Rick explained that moving forward, any large-scale economic problem will pose massive problems for Trump with the people who voted for him because of economic anxieties, and pointed to Conor Lamb’s election as what could be waiting for the President before too long. That led Ana to ask about what sort of platform Democrats should run on. The answer both landed on was not on impeachment or corruption, but on accountability and a message that makes people excited about going out to vote.

Alongside the conversation about messaging and the upcoming midterm election, Ana and Rick dove into the Trump Administration’s ongoing negotiations with North Korea. Despite recent positive developments, Rick reminded listeners that progress has happened before, and sounded a note of caution about hopes for a long-term solution.

“If Donald Trump manages to in some way help broker a non-nuclear North Korea, God bless him. Halle-fucking-lujah. Great job. That said, I am deeply skeptical of any kind of deal that isn’t a done deal,” he explained.

Before their conversation ended, Ana brought up Rudy Giuliani’s disclosure to Sean Hannity that President Trump repaid Michael Cohen for his $130,000 payment to Stephanie Clifford. Rick, a former Giuliani staffer, had a typically witty take.

“The surviving Rudy alumni society’s email chain last night was lit,” Rick said.

In addition to talking with Rick, Ira Madison III, the host of Crooked Media’s Keep It!, joined Ana to answer a listener question about having a conversation with someone who is racist but doesn’t want to admit it despite espousing openly racist sentiment. Ira addressed the inherent whiteness of the question, and found it difficult to understand why someone would ask it.

He spoke directly to the listener, and said, “I don’t know who this person is, but I would love you to stop talking with them. Ever.”

Although the two agreed on how they knew that it was a white person asking the question, because a person of color never would, they disagreed about what to do when you have an openly racist person in your life.

“If someone in your life is a racist, you have to decide, is this person important enough in some way to keep in my life, and that should be a pretty high bar,” Ana said.

Ira disagreed, and said that “they never are.”

Editorial note: In our April 20th episode, Ana talked to Chris Stedman about movement atheism and the alt-right. During the course of their conversation, Ana mentioned Sam Harris’ interview with Charles Murray, and said [34:16], “I’m thinking about Sam Harris and race science, and thinking I can’t possibly be a racist, because my feelings about black people are based on science.” Since then, listeners have pointed out that Harris himself was unequivocal that he does not endorse race science. He explained his own views at length in a joint-podcast episode with Vox’s Ezra Klein (here). Harris’ support of Murray is perhaps the more problematic aspect of this debate, not Harris’ support of race science itself.

Get in touch with us at withfriendslikepod@gmail.com or on Twitter at @crooked_friends.

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