Bill Simmons Talks Trump with NYT and Former Obama Speechwriter…Because That is Balance

August 18th, 2016 11:17 PM

Bill Simmons never promised to confine his HBO Show, Any Given Wednesday, to sports and sports alone. He also never promised to discuss politics with both conservative and liberal views represented.

So far, he’s living up to his non-promises.

On Wednesday’s edition of Any Given Wednesday, Bill sat down with New York Times writer Wesley Morris, and former Obama speechwriter Jon Favreau, to discuss, primarily, Donald Trump. I’m not sure why Simmons decided to talk about the Republican Presidential nominee with no Republican in the room, but my Spidey Sense tells me it’s because Simmons thinks having a Republican in the room (other than Caitlyn Jenner of course) would be icky. Here’s what the group had to say:


Bill: So Trump.

Wesley: Yeah. You just killed the whole thing, Bill. The energy was so good in here.

Jon: America was so great.

Bill: More likely Trump drops out before November, or Trump stages a massive comeback?

Jon: Comeback, I think. I just think there is no way that man drops out of this race. There is nothing about his personality that we've seen that makes us think he’s going to walk away. He's too narcissistic.

Wesley:  I think he can devise an excuse for having left. The thing he was trying to do with the setting up of the whole system being rigged against him in November I thought was really –

Jon: Then why not stay in? Then he could say was rigged when he lost. ‘I didn’t really lose, it was just rigged.’

Wesley: But then he has to spend the rest of his life having been the thing he's been spending the bulk of his professional pop culture career accusing other people of being, which is a loser.

Jon: Either way, he's a loser. If he loses, he’s a loser. This is why he's getting worse and worse. It's a spiral. When things go bad, they go bad.

Bill: Do see when the debates are coming, assuming he actually does the debate, do you predict loose-cannon Trump, or do you predict kinder, gentler, I almost seem like I'm sedated Trump?

Jon: I predict loose cannon Trump, but I have this nightmare that the entire campaign has been one big con, and like Trump shows up at the first debate with his pleasant tone and moderate policies and says hello everyone. I don't think that will happen, but in the first debate with Obama, Romney showed up and kind of, like all of his positions were different, he was moderate, Obama wasn't prepared.

Bill: That was a bad debate for Obama.

Jon: Horrible debate.

Wesley: But, I will say, I don't think that is going to happen, ‘cause who is his debate coach now? Roger Ailes is helping him prepare for these debates? I mean --

Jon: Well, the merger is official before the Trump campaign and FOX.

Wesley: Hillary Clinton, it will be interesting to see her in this position as a debater with somebody who, whether he's prepared or not, is not going to be able to talk the way she can talk at length about any policy question they possibly could ask her.

Bill: And is also willing to cross any line. Do we think he is going to use an expletive?

Jon. Yeah. I think, the pinnacle of this campaign, or the low point of this campaign, I've always thought it was Trump throwing an expletive at Hillary at some point in one of these debates

Wesley: That’s actually –

Jon:  I don't think that is out of the question.

Wesley: My nightmare has been just utter disrespect to her during a debate.

Jon: He talked about the size of his dick on a debate stage during the primary.

Wesley: All bets are off!  What he said about Rosie O'Donnell whle, he throws Rosie O'Donnell under the bus to get himself out of driving a bus even more over Megyn Kelly. I think he can say anything.

Bill: So do it in like a passive-aggressive way. ‘Well, that is why you killed the Vince Foster, so anyway’ – And then it would be like ‘Wait, what? What did he say?’ [Wesley laughs]

Jon [playing Trump]: ‘I don't think that's true, but many people have said you killed Vince Foster. That’s just my thing.’

Bill: Oh yeah, he does --

Wesley, playing along: ‘There’s something going on with this Vince Foster.'

Bill: ‘Vince Foster, we’ll never know what happened there,' and then just turns and goes back to his policies.

After a chat about what happens to Trump after he loses -- they went with the conventional wisdom about starting a Trump TV channel -- Fauvreau really drew out the praise for President Obama:

Bill: What was he like as a boss?

Jon: He was the best boss I ever had.

Wesley: Burn, big burn!

Jon: No, he never lost his patience, never raised his voice, was always calmer than anyone else who worked for him. That is the temperament, you don't realize that, but that's the temperament you need in a president.

Bill: Are you talking about Trump or Obama? [Laughter]

Jon:  No, but that is true, whatever party you are from, like I think you need that calm personality, like, not focused on short-term problems that you may have, now focused on the news cycle all the time.

Wesley: This is also a guy who is spiritually Hawaiian. And he's got chill. I think people who wanted like, like a crazy black man to be in the White House and people who feared a crazy black man being in the White House --

Jon: Well, don't think that wasn't in the back of his mind.

Wesley: Oh, of course, but that is everything you get as a black person.

Jon: You know subconsciously he is thinking to himself, I'm not going to be the angry black man. I have to avoid that --

Wesley:  Right. But if you got to college as a black male, you are aware that white people are watching you. And if you have any ambitions to go, to do anything important, that there is this other self that you have that you have to keep in check. But  I think he is just naturally chill.

Jon: That’s true.

Bill: My theory about the presidency, which I think both of you have heard, is basically our stepfather. We are not related to them, we didn't choose them, but they are there and you kind of have to make do. At that point it can go any way. Like with your stepfather he could be a good guy. He could be a surrogate father, pay for stuff. Or he could be an absolute nightmare. He could be like Robert DeNiro in This Boy's Life. Obama is about as good of a kind of stepfather president as we are going to get. You can pick his policies apart forever --

Jon: He also, he came to the White House not that far removed from being a normal human being.

Bill: Right.

Jon: And so, like, he used to say that when he was running in '08. Michelle and I know what it is to be normal. Not just paid off our loans financially, but we had friends, we had fun, they didn't spend all of their lives in Washington.

Bill: And you think he is the last great pop culture president?

Wesley: Yes, basically yes. He is the first and he is the last. He has created popular culture, popular culture has responded to him. A lot of the things that people find fascinating about him have nothing to do with policy. Unlike Bush. It's not about what Bush did, it's about with Obama, who Obama is or who we think he is.

Bill: I do feel like twenty, thirty years from now, we're going to be like remember when we had that president who is really funny at the Correspondents Dinner and who could give a speech to 15,000 people and seem like Cyrus from The Warriors?

Jon: It’s like he’s chill, but he’s also self-confident, and I think  a lot of that comes, cause in politics, you are always nervous, you’re always cautious. You are always saying ‘If I say that I like this song, is that going to hurt me? If  I like this, if I talk about the sports wrong?’  You know, like he just doesn't care as much. He knows who he is, he feels comfortable,

Wesley: He knows what he knows.

Jon: And he knows what he knows. And that leads to all that, you know?

Bill: You helped him work on the speech that he gave at the DNC. What was his demeanor during that whole thing?

Jon: He was very excited to give that speech. Like I walked, I saw him Tuesday morning before that speech, and I walked into the office and he was like, I'm ready to give this right now, let's do this. And you always know when he is excited about giving a speech a few days out, it is going to be a good speech.

Wesley:  He was like in the back saying I'm ready to go.

Bill: What else do we see them doing?

Wesley: I think Obama wants to shape an aspect of the culture, at least that's what I'd like to see. I'd like to see him weigh in on things and just sort of pontificate.

Jon: In that convention speech was that he just gave, when he said, you know,  democracy, you have to want it to make it work. That is what he wants to do post-presidency, make sure that people are into it, that they're willing to participate.

Utterly horrifying that Favreau considers pre-presidential Obama to be “normal.” Though, if you consider organizing poor people to protest in favor of policies that won’t help them, and launching your political career in the living room of a known terrorist to be normal, well then maybe he’s on to something.

It also in no way corrects the stereotype that the American man has gotten soft, when we see three grown males snorting and guffawing over the toughness of a 67 year-old woman notorious for lying about being an Indian. Then again, it’s an Obama speechwriter, a New York Times guy, and a liberal sportswriter.

What do you expect?