Newsletter 112: Anthony Scaramucci, Civility and How We Will Be Judged

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I’ve decided to start putting some of the best newsletter essays here on Medium, so more people can read them. You’re still better off just subscribing. Here is last week’s newsletter, about interviewing Anthony Scaramucci at this particular moment in human history. I enjoyed my friend Jason Gay pointing out that I look like I’m acting out the LeBron/J.R. Smith meme here.

You can watch this whole show on Amazon or on SI TV.

Friday night, at the Red Hen restaurant in Lexington, Virginia, presidential press secretary Sarah Huckabee Sanders sat down with her family for a meal. According to a server there, the meal lasted about two minutes. The owner of the place, recognizing Sanders as the most forward-facing member of the Trump administration, kicked her and her family out before they even got their menus. This has led to the usual cycle of recriminations, with one group of people flooding the Red Hen with negative Yelp reviews and calling them Nazis and another group of people saying the owner of the place is heroic and a true patriot. All roads end up with one group of people yelling at another group of people. I once joked that you could put up a picture of a cute puppy on a random Yahoo blog page and comment three would be “Obama’s a Muslim!” and comment 13 would be “Bush took down the World Trade Center!” (Comment 17 would be “First!”) On Twitter no one even waits that long: Eventually, the Blinking Man GIF and Pepe the Frog are coming.

The source of the Red Hen owner’s decision, though, is one that is deeply relatable: Helplessness. Every day brings some sort of new horror, with this week bringing some of the worst of them, and it is difficult to sit by and watch them get away with it. You want to do something, and simply Trying To Get Out The Vote can feel inadequate. There are monstrosities happening out there, every day, every second, and they are happening in our name. What can you do? I touched on this in my previous newsletter about Being Followed By Kellyanne Conway, but the helplessness makes you want to find anyone connected to this madness and scream at them to STOP! Most of us aren’t White House reporters, or even slightly adjacent to the political process and those in charge: You can feel so impotent, just sitting and watching it happen. And just going on social media and yelling about it — especially if it’s the only action you take — can feel like it’s making the problem worse. You want to be angry, you are angry … but being angry all the time is no way to live. It’s a quandary, captured well, I thought, by a Grierson Tweet of last week.

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So when you have that moment, like the Red Hen owner, to actually say something, to confront one of the people responsible for this and for defending it, you can’t help but want to make your stand. It’s a small thing. It will probably cause you even more headaches in the long term. There are even some good moral arguments against it. But one of them is right there. You want to be able to say, when all of this is over, when we’ve hopefully survived it, that you said something. That you stood up. That you made it clear to everyone someday looking back: I was not OK with this.

Which leads me to the episode of “The Will Leitch Show” we taped this week.

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No, not that one, though Lea Thompson was wonderful and honestly one of the most pleasant people I’ve ever met. But not her. Him.

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It felt like a photo you don’t smile for.

We booked Anthony Scaramucci as a guest weeks ago; he’s friends with a previous guest who told him coming on my show was a good time. Ever since we booked him, I’ve been agonizing over the show, how to handle it, how to get the right tone down, how to talk to him without screaming, how to balance my natural affability and desire to please with someone who, I think, is connected to this mess and must be confronted about that. One thing I did not consider, however, was not having him at all. When I put up an Instagram post of that picture, a few commenters said that simply sitting down with him was somehow appeasement, or “normalization.” I suspect this is a reaction to the infamous Jimmy Fallon moment when he tousled Donald Trump’s hair, a moment that Fallon will never live down and never should. But there was no way I was going to be, “Hey, it’s The Mooch! Mooooooooch! Love this Mooch!” And I don’t understand why sitting down with someone with whom you disagree, someone defending something you find abhorrent, is somehow “enabling.” The idea that you’re supposed to just piss on the shoes of someone on the opposite side of you — or even that everything is a “side” — is one of the things that got us into this mess. Though, to be clear: What really got us into this mess is people like him.

I wanted to have this discussion, and I wanted to have it in, yes, a decent, civil fashion. I do think there is a place for that and, frankly, don’t feel particularly apologetic about it. I know Twitter would have me punch the guy in the face when he walked into the room, but that does nobody any good and is just empty talk; none of the people claiming they want that would actually do that in that situation, and thank heavens for that. So I was ready for the interview. I talked to many close friends and associates about it. I mapped out every question, and possible followup. I even got myself a special lapel pin for the occasion.

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And then the child separation story exploded. Suddenly an urgent moral imperative became an urgent moral emergency. It got a lot more difficult to remain emotionally detached. And it put everybody in a much more defensive crouch … or a much more eager position to fight.

So, we did the show. How did it go? It was very tense! I am not inherently a television professional, and I also have a quality inherent to my personality to try to make people feel at ease, even if I don’t want them to. But I also felt like I need to push, at every opportunity, and it led to an interview that was awkward and uncomfortable and, above all, exhausting. Scaramucci was against the child separation policy — which, you know, good for you! — but supported Trump wholeheartedly otherwise, including repeating his absurd claim that Trump “is the least racist person who ever lived.” (I asked him who the second-least racist person was, and Scaramucci said it was his late Uncle Sal. I turned to the camera and said, “Sorry, Sal: You were so close. Second place is nothing to be ashamed of!”) It is worth noting too that Scaramucci is in fact not part of this administration right now; he’s just a guy who defends it on television. There is only so much feet-to-fire you can do there. I pushed. But I am not Jake Tapper, or Mike Wallace, or Chris Hayes. I am not a confrontational person at my core. I did the best I could. But I did not piss on his shoes.

But you want to do something. You want to make sure people know where you stood. The one thing I wanted to make sure to say, the one thing I was gonna say no matter what, was my final question. I’ve written before about worrying about what my boys are going to say when they look back at this era in 30 years, when they look back and wonder “how did my parents handle that? How did they react when faced with this?” It makes you want to make sure everybody knows where you stood, that you were on the record. So I asked, essentially, the question I want to ask all of them: Because of your connection to this, your grandchildren are going to be asked about you their entire lives. They are going to be connected to this, no matter what. Long after you are gone, everyone in your family will be known for this connection to what’s happening right now. Are you OK with that? They’re going to be apologizing for you their entire lives. People are going to be whispering when they enter a room forever. Is this worth it? Is this what you want to give them?

I probably stumbled over that question and didn’t ask it as forcefully as I imagined it in my head. But I did ask it. We all do what we feel we have to do. We take our stand in our own little ways. It’s probably inadequate; it’s surely not enough. But someday the kids are gonna ask. You have to be able to show them something.

The show will be up next week. I’m sure I fumbled some stuff, most stuff. But I did my best. We can only do what we can do. I wish it were more.

Written by

Writer, New York, NYT, MLB, WaPo, others. Founder, Deadspin. Author of four books, with fifth, “How Lucky,” coming May 2021. https://williamfleitch.substack.com

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