Opinion: 10 questions I can’t wait to ask Rick Wilson at Uncharted

Republican political strategist and #NeverTrumper Rick Wilson and I disagree on most things politically, but I am looking forward to hearing him at Uncharted, and I have questions.

Since its inception, I have wanted to attend Berkeleyside’s Uncharted Berkeley Ideas Festival, but I have always had a conflict. This year, I am finally able to attend, and I’m especially excited to hear Rick Wilson.

Rick Wilson is a veteran Republican political strategist. Rick is known for his keen insights and sharp wit. I also appreciate how well-read he is. But Rick is recently best known for his role as a #NeverTrump-er: a frequent guest on Real Time With Bill Maher, his Daily Beast column, his behind-the-scenes Periscope broadcasts, and his new crowdfunded documentary, Everything Trump Touches Dies.

Politically, we disagree on most things. But, we can both recognize crazy. I can’t wait to meet Rick at Uncharted, and I would love to hear how he would answer these questions:

  1. How sophisticated do you think the Russian bot attack was with regards to application of data, and where do you think that data and expertise came from?
  2. Are any there any viable trans-electoral approaches to our current political crisis? Impeachment? The 25th ammendment? Or, does it come down to the ballot box in 2020?
  3. Who could successfully challenge Trump in 2020 on either the Republican or Democratic side? Third Party?
  4. Evan McMullin seems to be a genuinely good guy, but he felt like a candidate from the 90s, and seemed out of touch with the mood of everyday Republicans. If he can’t excite “the base,” how can he excite the nation?
  5. Where’s Rudy Giuliani?
  6. What do you see for the future of party structure with regards to both Democrats, Republicans, and potential splits in each party?
  7. You are BFFs with Louise Mensch, but you never promote her direct reporting, especially her most colorful allegations. What do you think of deep #TrumpRussia?
  8. Although your politics differ, you and Matt Taibbi have razor sharp, acerbic humor. What do you think of Matt?
  9. Recently, you tweeted “Some days, I swear. I just finished a meeting in Hollywood, because that’s my strange new life.” What do you make of the intersection of celebrity, social media and politics?

And of course, wanna go to Top Dog?!

Welcome to Berkeley, Rick. I know you will be treated warmly!

Rick Wilson will be in conversation with Peter Leyden at Berkeleyside’s fifth Uncharted Berkeley Festival of Ideas in downtown Berkeley, on the afternoon of Saturday Oct. 28 at the Freight & Salvage. See the full program and buy tickets at BerkeleyIdeas.com

John Holland is a Berkeley resident and an armchair political scientist.