20 Questions With Sean Spicer

On Debate Day morning, who better to have for a round of 20 Questions than Sean Spicer? Inspired by Vanity Fair's renowned back page series, which offered a playful yet insightful look into the minds of celebrities, politicians, and cultural figures, the acclaimed author and former White House Press Secretary to Donald Trump answers everything from his thoughts on Karine Jean-Pierre and friends voting for Biden (we all have them!) to the motives behind his recent Substack debut and new role as producer for Trump's "Front Row Joes,” a documentary highlighting the passionate supporters at the core of Trump's base. With a front-row seat to the action for decades, it's a pleasure to have Sean here today to indulge our politically-themed curiosities leading up to tonight’s match off.

---

1. What do you love most about where you live?

We live in Virginia  - just outside of Washington. I like the proximity of being close enough to DC that I can run in for a meeting, meal or game (although its not that often) but not having to live with crime and politics of  Washington. We have a great neighborhood with places for the kids and play and restaurants that are walkable. 

2. What does your morning routine look like?

Although I am trying - slowly - to break the habit, I immediately grab my phone right when I get up around 6:30 to check texts, emails, and social media. Once the kids are off to school, I usually get in a quick workout where I am clicking from morning show to morning show trying to get a sense of the issues that are being talked about and some the guests that are weighing in. My daily show/podcast tapes in the late morning, so I am trying to get the most up-to-date topics, issues, and guests as soon as I get up.

3. Something simple in life that is currently bringing you joy?

A smile on one of my children’s faces never fails.

4. What traits do you value most in a man?

Loyalty and trust. My father taught me early on that your word was your bond, and a handshake meant something. I value people I can count on to keep their word and keep our discussions private. Too many people want to share everything and can’t be trusted. If you can’t trust someone to keep their word, what can you trust them with?

5. What traits do you value most in a woman?

The same qualities I look for in men - loyalty and trust - are the same I look for in women.  

6. One song you never get tired of?

Don’t judge, but Sailing by Christopher Cross always gets me in a good mood. I grew up sailing, and my father sold boats for a living, so the song invokes very positive memories and never fails to make me smile. Overall, I am a huge fan of Yacht Rock (who isn’t). 

7. Do you ever worry that Taylor Swift is secretly working undercover as a highly influential DNC operative?

I didn’t think it was a secret anymore.  

8. How old were you when you knew you were conservative?

20ish. My father sold boats for a living — and when the luxury tax was passed into law, a lot fewer boats were sold, and a lot of jobs were lost. I saw firsthand the impact misguided left-wing policies have in the real world and, in particular, on our family.  

9. What do you find most inspiring about current times?

Post-covid, a lot of Americans saw firsthand the impact leftist policies were having on them and their kids and have decided to jump into the arena in some way - some as candidates and some just as more active citizens. I really believe our country is at a tipping point and facing some real serious issues both domestically (debt, deficit, and social media) and internationally (China). I admire the people who are willing to stand up and fight for future of our country.

10. What do you find most annoying?

Two things. First, the lack of appreciation by so many for how great this country is and the lack of appreciation to honor those who have fought and sacrificed to give us all the freedoms we enjoy today. Second, people who lack situational awareness. People who have conversations on speakerphone in public places drive me nuts. With all the covid funds couldn’t we have sent everyone earbuds?

11. Would you rather be stuck in a forest with Hilary Clinton or a Bear?

No question about it - Hillary Clinton. The bear would easily crush me in short order — whereas I could easily tune out Hillary.

12. What outlets do you trust these days for news updates?

I don’t trust outlets; I trust people. There are a bunch of journalists who have a strong track record of taking time to really understand the process and are well-sourced. Too many, though, are in pursuit of the clips and clicks.

13. You are new to Substack. What brings you here and what does your newsletter entail?

I have been sending a newsletter to subscribers for a few years, but Substack gave me an opportunity to bring it to several new audiences and expand my reach. The full spectrum of thought—far left to far right—is on Substack, and my goal is to reach them all.

14. As someone who’s worked in and around politics, witnessing and shaping the inner workings of DC, how would you say both parties have changed over the years, if at all?

A few big things have changed. The amount of money in politics has skyrocketed, as has the amount of time candidates spend raising money. Since Republicans won back the House and Senate in 1994 (Contract with America), the parties have become more institutionalized in the process - both legislatively and politically despite the media narrative, I think play a much larger role. Think about the number of members of Congress who vote almost entirely with their party leadership.   

15. Is anyone in your life voting for Joe Biden?

Unfortunately — I'm working on them, and most of them live in states that won’t affect the outcome.

16. Thoughts on RFK Jr. and his role in this election cycle?

RFK has been interesting to watch. I wish he had stayed in the Democrat primary and made it more of a race for Biden. If you look back on the past couple of cycles, third parties, or the lack of them, have made a big difference. In 2016, Trump won Michigan by just over 10,000 votes — and Jill Stein the Green Party candidate, received over 50,000. While Stein didn’t win any states I don’t think there is a question that she had an impact. RFK won’t win any states but he could take away enough from Biden or Trump in a few states that could have an impact on the outcome of key states that get you to 270 electoral votes.  

17. Is the Donald Trump we see today any different than the Trump we met back in 2017? 

The only difference between Trump of then and now is he is much more aware of the system and who is with him, and who is against him.

18. How would you describe the Front Row Joes? What about them interests you?

The Front Row Joes are the Deadheads of the Trump movement. They are the men and women who have attended 50, 60, 80 rallies and events for Trump. I wanted to make this documentary because there has not been a political movement like this in our history on either side of the aisle, and if we didn’t follow them around and explain who they were and what made them tick, no one would. Some of the folks are spending over $50,000 a year following Trump. It’s one thing to be a fan or a superfan, but these folks head to rallies days in advance and sleep in their cars to be in the front row, rally after rally. Go to SalemNOW.com to check it out — you can even gift the movie to a friend…..or a Trump hater.

19. On Debate morning - any flashy last minute predictions for what we can expect or who might show up as Trump’s grand VP reveal? 

I would be shocked if he announced his VP before the debate because he doesn’t want to take away from the significance and eyeballs debate night will bring. If for some reason he needed to shift the narrative after the debate, I could see that being a time to announce the VP.  My guess is he will want his on-stage performance to stand on its own. Trump has all the upside coming out of debate - Biden has a lot to lose.

20. Lastly, how would you rate Karine Jean-Pierre on an end-of-term press secretary report card?

What’s lower than an F? She is historically unqualified, and if it wasn’t for a press corps that fawns over Biden, her world salads, misstatements, and falsehoods would garner much more attention.

---

Related:

Spicer’s book’The Briefing: Politics, The Press, and The President

SEAN SPICER: Trump Supporters Deserve To Be Covered In A Way Liberal Media Refuses To

“Whether you love or hate Trump, it’s obvious that the movement he started in 2015 is truly historic. No other figure from either party in modern American history has come close to leading a movement like this. In the documentary, person after person (including President Trump himself) likens what he started to the super fans of a rock band, and they are right.

Until they start doing so (I wouldn’t hold your breath), you’ll have to continue to seek out independent media to get the full story.”