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21 Questions For 'FOX & Friends Weekend' Co-Host Will Cain

Will Cain on the set of "The Will Cain Show."

After five years at ESPN, Will Cain left the company this summer for a fresh opportunity. That new gig will be at Fox News, where Cain will be a co-host of "Fox & Friends Weekend" starting Saturday.

In his new role, Cain will be dipping back into politics, which is where he got his start in media. He previously worked for CNN and The Blaze before joining the Worldwide Leader.

We caught up with Cain recently for our "21 Questions" series. In our conversation, we discussed what he'll be doing at Fox News, his favorite debating sparring partners, his time at ESPN, his recent family road trip and more.

Let's get started:

1.The first, most obvious question is how have you and your family been able to handle this whole pandemic?

WC: Thanks for asking. We’ve handled it together, as a family. I know this has been an incredibly difficult time for people physically, spiritually, and economically. And I don’t think enough attention has been paid to the effect on children. But it’s also a time that has clarified what and who are the most important in life. We’ve traveled the country, gone through career and life changes, talked about our values, hiked, and spent time together as a family.

2. Your new role on "Fox and Friends" begins on August 15. Will you be discussing more politics, more sports or a little bit of everything?

WC: A little bit of everything. I’m excited that this move is not closing doors on topics and content, but opening new doors to connect with the audience.

3. Outside of the material itself, how different is preparing for a political show than preparing for a sports show?

WC: No different. I always saw my job the same regardless of the content: tell the truth. Yes, be smart, read vociferously, study, be entertaining, have fun, debate with goodwill, work hard. But above all: tell the truth.

4. You're a die-hard Dallas Cowboys fan. What's the most-painful loss you've experienced?

WC: The Catch. The 1981 NFC Championship game. It’s my first real sports memory. My parents had a watching party and I cried. I was devastated and embarrassed. Joe Montana and Dwight Clark made me cry and I’ve never forgiven them or the 49ers.

5. Rank the places you've lived in from best to worst (or best to least best): New York, Montana, California, Texas

WC: It’s definitely best to least best. I have - to some degree - loved every place I lived.

  1. Texas - I’m a Texan. It’s who I am. I don’t expect or need everyone to agree, but Texas will always come first.
  2. Montana - I moved to Montana for two reasons: “Lonesome Dove” and “Travels with Charlie.” In “Travels with Charlie”, Steinbeck says if you asked a 10-year-old boy from Washington DC to describe Texas, what he would in actuality describe would be Montana. Montana lived up to these lofty expectations. But even better than the beauty and the culture were the people. I love Montana.
  3. New York - Though I am very worried for NYC’s future.
  4. California - I do think if I lived in CA again as an adult, it would climb these rankings.

And although you didn’t ask, we spent most of our quarantine in East Tennessee and quickly grew to love the Volunteer State and the people there.

6. As a Texas fan and UT law school alum, who is the one player you wish Texas football could have landed but didn't?

WC: Adrian Peterson. There is a list of quarterbacks that Texas could’ve and should’ve had that includes Robert Griffin, Johnny Manziel, and Andrew Luck. But I don’t remember a recruiting loss that hurt more than Peterson and I think Mack Brown agrees.

7. We did a recent Q&A with NFL Network reporter and fellow Texas alum Jane Slater and she was a bit less than complimentary about Tom Herman. What are your thoughts on the job he has done?

WC: I like Tom and I am rooting for not just Longhorn success but also Tom Herman success. I think this year will define that success. He’s shown progress and had some nice bowl wins. But for better or worse, success at Texas is defined by championships. And in year four, with Sam Ehlinger, championships need to be won.

8. As a Cowboys fan, what do you think about how this whole Dak saga played out and where do the two sides go from here?

WC: Dak will be the long-term franchise quarterback of the Dallas Cowboys and one of the best QBs in the league. I didn’t expect the franchise tag but I do expect they’ll work out a long term deal.

9. Is Ryen Russillo more jacked or less jacked than you would expect in person?

WC: Haha. More? I don’t know what you expect? I should say “less” just to get in his head a little and make him squeeze out a few more reps. But, Ryen is jacked.

10. You get $10K for a layup, $100K for a free throw, $500K for a 3-pointer and $2 million for a halfcourt shot. You can only take one shot: which one?

WC: $500k for a 3-pointer. Half court will never be better than pure luck for me. I can hone my three for some decent odds at half a million.

11. Where can one find the best BBQ in Texas?

WC: Well everyone says Franklin’s in Austin but I’ve never been there. So for me it’s Kruez Market in Lockhart, TX. Just go to Lockhart and you’ll hit the best: Kreuz, Smith’s Market, Blacks Barbeque. Chisholm Trail.

12. You played collegiate water polo. What are some things about the sport that the average sports fan might not know?

WC: The size of the players. Most, not all, but most are NFL tight end sized. 6’4, 230.

13. What reporters/analysts have you most enjoyed debating or discussing things with on the air throughout your career?

WC: Stephen A, Russillo, [Kate] Fagan, [Dan] Orlovsky...there are so many more and too many to list. So let me limit it to this: my former producers Nuno, Bubba, Mike A, and Pat, and the listeners of the Will Cain Show who challenged me every day.

14. Can you tell us a little more about the recent road trip you went with your family? What spurred it on and what moments stood out for you from it?

WC: We were gone for almost four weeks, traveled almost 7,000 miles, and hit 15 states.

Although we saw Yellowstone, Zion, and the Grand Canyon, the highlight was probably frog gigging (first time in all of our lives) in my hometown. Both of my boys caught giant bullfrogs.

America is an overwhelmingly beautiful place. Every state is awe inspiring in its own way. I mean that. It’s stunning. But, even more impressive is her people. Americans are tough...and caring, they are obstinate...and rational, they are innovative ...and resilient.

15. Many of ESPN's prominent personalities either are or are perceived to be left-leaning. It seems like you were always pointed to as the guy "on the other side." How did you feel about that?WC: It’s true. I represented a minority viewpoint in sports media. There are others who share my views but don’t feel comfortable expressing them publicly. I felt comfortable because I knew my views are not extreme or even in the minority across this country. Also, I was right. Sports media is out of touch.

16. Most underrated Dallas athletes of all time? Any sport.

WC: 1. Dirk Nowitzki. Dirk was revolutionary. A top 5 power forward of all-time, a top 20 player of all-time, and one of the few to win a championship when not surrounded by a super team. Dirk is recognized nationally but not fully appreciated.

2. Darren Woodson.

3. Both Aikman and Romo are underrated but Dak Prescott is on his way to being the most underrated quarterback of all time.

17. What is your guilty pleasure television show

WC: Survivor, Love is Blind, and I’ve recently made it through more episodes of Floor Is Lava than I care to admit.

18. If you had focused on law and were a practicing lawyer right now, how do you think your career would have turned out?

WC: I think I could have been a successful trial lawyer.

19. Who is the person you would most like to interview that you haven't already?

WC: Charles Barkley (and I soon will).

20. Fishing or hunting?

WC: Hunting.

21. Who was the most influential teacher or professor you had during your time in school and why?

WC: I could give a long list of names from elementary to law school but I learned the most debating my dad at the dinner table.

You can read more of our interviews with sports media stars here.