The Bill Simmons Podcast - Ep. 75: Jon Favreau and Dan Pfeiffer

Episode Date: March 11, 2016

HBO and The Ringer's Bill Simmons welcomes Jon Favreau, former director of speechwriting for President Obama, to break down the 2016 primaries, Donald Trump's lack of a speechwriter (10:00), and this season’s WWF-style debate format (21:00). Then, Dan Pfeiffer, former senior adviser to Obama for strategy and communications, joins to discuss Ted Cruz's lack of likability (26:30), advising the Trump campaign (31:00), the Obama-Clinton Cabinet dynamic (39:00), Obama’s post-presidency (45:00), flaws in media coverage (50:00), and the impact of technology on the political landscape (1:05:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Yeah. Okay. Yeah. We were big Tupac. Big Holy cross week here on the BS Podcast. Joe House and I talked about Holy Cross somehow sneaking into the madness. And now Jon Favreau here, former Obama speechwriter, but more importantly, a Holy Cross graduate. 2003.

Yeah. That was really the last decent run for holy cross hoops the last ralph willard era the ralph willard era very close three years i was there uh oh one oh two and oh three we made the tournament and then every time lost in heartbreaking fashion in round one yeah yeah and blowing leads in 2003 we were up against Kansas. And I remember we were leading by five with 10 or 11 minutes left. And it was just pandemonium at the school. And we almost didn't even care. We were just like, the fact that we got that close.

We never had that moment where we just, that one upset that I think would have gotten the momentum going. It just never happened. I know. So when you graduated, what happened next in your life? How did you end up in the White House? So I graduated and I had done, Holy Cross has like this DC internship program. Yeah. Junior year. So I went and I was an intern for John Kerry because he was my home state senator. Yeah. And it was right when he was preparing his presidential run. So I ended up sitting and interning with his communications director, speechwriter. And I thought it was a great job. And when I went back to Holy Cross, I basically bugged him every single month, the communications director, this guy named, uh, for a job on the campaign, any job.

Uh, he didn't call me back until the night before graduation at Holy cross. And he was like, so, uh, good news is I think we can get you on the campaign as an assistant. Uh, bad news is,

uh, we're not gonna be able to pay you anything at all. And I was like, what? And I'm just like, there's like a pause in the line. And I was like, what? And I'm just like, there's like a pause in the line. And he's like, I'm just,

I'm just fucking with you. So, but it wasn't much. So I went there and I was, I moved to DC like two weeks after I graduated and I was a press assistant, uh, on the campaign. And then when Carrie looked like he was losing to Howard Dean,

yeah, they needed a deputy speechwriter. No one would join the Kerry campaign at that point. It was a sinking ship. They didn't have money to pay a real speechwriter. They were paying me like $20,000 a year. And so they were like, you know what? Let's just promote Favs and make him deputy speechwriter because this thing is probably going to be over anyway.

Yeah. So they did. And then Kerry wins the the the uh primary and uh and so i was his deputy all through the all through the year general now when kerry loses um at one point during that campaign robert gibbs who was my first boss uh had gone to had quit the campaign and went to go work for brock obama so obama wins the senate seat in 04 carrie loses the presidency and gibbs reaches out and says you know obama's never had a speechwriter before and i i'm trying to convince him that now he's in the senate he's going to need a speechwriter and he's sort of resistant to the idea but why don't you come have breakfast with him because

he liked writing a lot of his stuff right yeah no he wrote the 2004 convention speech by himself yeah and he didn't think he needed a speechwriter and so we have we have this uh this breakfast meeting obama's first week in the senate and it's like a really easy interview you know and he's just where'd you grow up where'd you go to college why'd you get into politics all this kind of stuff and at the end he's like you know uh i don't think i need a speechwriter but gibbs keeps telling me i do and you seem nice enough so let's try this out wow and that was it that was it when did you think he had a chance to actually become the president like what year oh six oh six oh five and oh six i mean it was funny i i had this bet with with robert gibbs um because he was like you know hillary clinton's

going to be the nominee in 08 and i said i just don't think i don't think the party's going to go with her yeah and he's like well who do you think who do you think it's going to be and he's like you think it's going to be our old friend john kerry you think it's going to be john everett's i'm like no i don't think it's going to be those guys either i just think i'm like what about our guy and and uh gibbs is like there's no way he's gonna run at this point he just got here it's not gonna happen and i'm like i just i know that hillary won't be the nominee and um and gibbs is like i will bet you a dinner of kobe beef that that hillary clinton is the nominee of our party wow he's still not paid that bet yet seriously after eight years i know it's it's bullshit um when you think about like he didn't

have a ton of experience no before he became the president which is the big thing everyone's using against trump right now right not that there's not a million different things to use against but i mean the history of politics there's a lot of people who didn't have a ton of experience that yeah kind of snuck into the white house when you were when he actually got in and when i when i interviewed him for gq and he talked about that first year you think you know what you're doing but um do you remember feeling overwhelmed those first six months i felt a little overwhelmed but it was actually a little bit easier for me because on the campaign there was i mean speech writing is all about how many people you have with writing right yeah like the more writers you have the easier

your job is and in the campaign there was first just me and then me and two other people and then a couple more and then by the time i got to the white house i had a team of speech writers and so the workload wasn't as bad as it was in the camp so you're like kind of uh sprucing up other people's first drafts and things like that sometimes? I was doing more editing. Yeah. So that part was better. The problem with the White House, I mean, the real challenge in the White House is not that you're working around the clock.

It's that you can't, you have no, you can't plan any time. You can't plan a weekend. You can't plan, because if something goes on in the world, the president has to comment on it. Yeah. And so, you know. You're talking about you couldn't plan anything. Right. No. I mean, it was like I could be out at a bar and suddenly something horrible happens and then that's it.

I'm done. I'm back in the White House and there until 2 in the morning. And that's why you didn't have alcohol the entire time you worked there. The whole time. I was sober. You're sober. It's amazing. Yeah, no.

I mean, it was when I remember walking into the White House when we all got there that first week. And there was a moment where Obama invited sort of all the communications press, speech writing staff who had mostly been on the campaign into the Oval. And we all sort of walked around the Oval together looking like, what are we all doing here? And it wasn't like we're here with the President of the United States. It's like, we're here with Barack Obama, who we've known for the last couple years. And who just, how did we all get here? What the hell is going on? Did you see, when did you notice people just changing the way they acted around him?

Not the inner circle people, but just in general people. Fairly quickly once he was elected. It didn't happen before? No, I think in the camp, because he's just such a like laid-back person yeah i mean the whole like the kind of aura of celebrity that grew around him yeah was invisible to most of us during the campaign because we were working so hard oh yeah you're in it so it's like you didn't have time to sit there and step back and think you know what's going on? He's the most one of the most famous people in the world right now because you were just trying to get through day to day.

Yeah. So there was almost never a moment. And that was pretty much true through the White House. There was almost never a moment where you could step back and appreciate or sort of sit in awe at all the things that were going on. You were on my radar pretty quickly because I was like the youngest successful holy cross person in that list they have with like clarence thomas i was like the last year it's you clarence thomas and chris matthews it was nobody after me so i kind of was like this is great i'm like the i'm like the young blood and then all of a sudden you popped in i'm like what the hell oh three now I feel like a dinosaur. But you stayed there.

How long? Five years? Yeah, I stayed in the White House five years. So I left in March of 2013. When you're in the campaign, like right now, like trying to get elected and he's giving speech after speech after speech after speech. Like how many are you writing a day? So you write a stump speech, which is the speech that the candidate delivers at almost every event. But then he does.

He ad libs a little bit off that. Right. So it's not the exact same every time. Ad libs off of it. And usually what you do something called a topper or insert so that you have the candidate respond to the news of the day. Yeah. And then just goes into the stump. Right.

And hits his like little touch points for what the campaign's about exactly yeah and then there are policy speeches so if he's rolling out his health care plan or rolling out a foreign policy plan then you've got to do those speeches so that happens so if you're trump do you have a speech like today's the speech i sound like a racist let's write that one i think he's got that one memorized yeah he's got no i, I mean, he's an interesting case because he doesn't have a speechwriter. Yeah. So he said, which I believe. I actually believe that too.

Oh, I totally believe it. I think he ad-libs this whole thing and he's actually really good at it as long as you're not listening to what he's saying. No, he has the whole thing down. Yeah. the whole thing down yeah trump my theory on trump is he is um a candidate who has basically just like what you what you'd get if you had someone who just watched cable news all day right and and specifically fox and listening to right-wing radio like if cable tv created a candidate had a baby yeah because he knows just enough it's all surface level yeah it's all bad news right it's all about how like everyone in washington of both

parties uh is a bunch of crooks and liars yeah it's all punditry it's all talking about poll numbers and this is like what he does he's he's better at political punditry and like reciting poll numbers and reciting like who's up and who's down and all that kind of stuff then he is about talking issues and you can see like in the debate last night, every time you press him, it's like an inch deep and a mile wide, his knowledge about just about everything. So if you press him more than like five or ten seconds on a given issue, he can't because he doesn't know. I mean, is Bernie Sanders that much different though in terms of being a surface guy? I think he's not. I think he's appearing that way because he's, I mean, Bernie Sanders is a great case in message discipline.

Yeah. Because he literally brings everything back to his Wall Street millionaires, billionaires message. Yeah. The reason I think he actually probably knows more is someone who's been in the Senate that long knows all the details of all these issues. It would be impossible not to. Yeah. It's almost one of the problems of being in the Senate or being in Washington that long is that you're so in the weeds on so many different policy issues that when you go out and speak publicly, like you start speaking in acronyms and you get really boring and

all that. So it's actually a credit to Sanders that he's able to distill a very, you know, powerful message, even though he has probably been passing bills with all kinds of acronyms all these years. You wrote a good piece, I think a week or two weeks ago, about Hillary Clinton. Yeah. Just about, you kind of flipped the narrative a little

because it just seems like people have spent the last eight, nine years figuring out reasons why she should not be the president. Right. And this whole other narrative has come out. and the way she's judged is interesting you know like my wife my wife oh my wife hates the way she dresses and she can't get past it and it brings it and every time she gives speech like oh my god oh gee and it's just people just nitpick nitpick nitpick because she's been in our lives since 1991, the first time. And it's just people just seem tired of her.

Well, I sort of came around to that because I was one of those people, obviously. I was on the Obama campaign and I had only seen Hillary. You guys were trying to beat her. We were trying to beat her. And primary campaigns, as we're seeing now, in some ways become even more intense than a general election. Because in a general election, you're fighting over issues because you have such different views. In a primary campaign, you're trying to stand out and win

based on personalities and leadership style. So it becomes more personal and nasty. And that was certainly the case with Obama and Clinton in a way. But we all saw her as horribly calculating and would do anything for political reasons and stuff like that and the more i got to know her and the more i watched her you realize like when she is sort of cautious in the way she speaks right but when you've been in politics for as long as she has yeah and you've been attacked as much as she has and you've been in politics for as long as she has, and you've been attacked as much as she has, and you've been betrayed as much as she has, and you've had people leak things about you and investigate you and all that kind of stuff, you're going to be a cautious person. Barack Obama didn't really have anything to lose in 07 and 08.

And so he kind of say what he wanted to say, you know, like much more cautious than he used to be. I think that's, I think once, once you come into power, once you're in the White House, once you're in office, you start becoming a little bit more cautious because you realize that the words you say, the decisions you make really have pretty large ramifications. So there's like sort of a natural caution that's built in. And I think that happened to her. And the tough part is if you've been in Washington as long as she has,

you almost have to unlearn all that for a campaign. But she's, you know, by far the most qualified candidate. By far. And I mean, that's, I was saying in my column that I didn't work with her very closely in the White House, but I would see her at cabinet meetings. I would see her in other meetings. And she was just, she was by far the most impressive cabinet member. And, you know, the president would like go around the table and ask everyone about their issues. And then he would ask Hillary about everyone else's issues in addition to her,

because when we were trying to pass healthcare, she had tried to do it in 1993. And so he's like, all right, Hillary, what do you think about this? And she just had all these lessons and all these ideas. And she's just a really smart person. She's well prepared. And she works her ass off, too. Yeah. Like, she just, and that's what everyone who's met with her think.

And Republicans in the Senate used to think that about her, too, when she got to the Senate. All these Republicans hated her. She got to the Senate, and then one by one they'd be like, you know, I worked with Hillary Clinton on this thing and she was pretty great. Now here's where everybody who doesn't like Hillary is saying, yeah, but you left out the part that Clintons are liars. All they do is lie.

All they do is lie. I mean, they've been caught in some pickles. Yeah. Well, look, I think it's tough. The reality is there's not a great choice this year. And sometimes that happens. I was saying that to, I forget who I was talking to about somebody, but it's like one of those sports years where a team just wins the title

and everybody just kind of looks around and goes, wow, that didn't really feel like a champion. I guess somebody had to win. I mean, especially on the republican side i think everybody's kind of looking around waiting and waiting and waiting it's like no these are the guys these are all of our candidates right here it's hard to recognize that at the end of the day politics is is about alternatives right and it's like you're not i mean we had a very exciting election in 2000 and 2008 and everyone was very inspired about Barack Obama.

Yeah. But also Barack Obama did not come into office and then fix everything with his magic wand. No. Right. And everyone's, oh, we're so disappointed now. But you know what? It's like things aren't perfect and it's not easy to fix everything and change takes time and all this kind of stuff. Sometimes you have an alternative and when you go through the ringer of a campaign, you're not going to look too perfect at the end or it's very difficult to. At the end of the day, you've got to ask yourself, okay, who's a better option here?

It's not always going to be inspiring or exciting, but that doesn't mean it's any less important is what i think you know like the difference between a hillary clinton winning this election and just about anyone on the republican side is enormous enormous because even someone who looks appears fairly moderate like a marco rubio would be the most conservative right-wing president we've ever had in the history of the country. By far. By far. Kasich, though. Kasich seems... I get in trouble for this because...

He seems like the most normal of all of them, right? I know, and every time I tweet about, like, Kasich seems normal and Kasich seems like a guy... People get mad? Yeah, they get mad because... I mean, I learn more about him. He has, like, an extremely pro-life record, like, more so than many of the candidates. A lot of people, my girlfriend's from Ohio and her family's in politics too. And they say, oh, he's very, very conservative.

He's not as popular in Ohio as people think he is. But most people will say he's a good man. He's a good man. He's a nice guy. He's not as politically craven as some of these people. I watched that show, The Circus, on Showtime. Yeah. And Earmuffs HBO.

And they're kind of flying around and talking to all these different candidates. And they're catching them in these, you know, they're not studio interviews. Sometimes it'll just be the guys standing backstage and they talk to them for five minutes. And Kasich seems normal. Like he could be here now and we'd be talking to him and it'd be like somebody's dad or something and he's the only one out of all of them who seems kind of normal those are the people those are the people that you want in politics right and it's also i don't think that's just like a good way to act because it's like morally right

it's also smart politics yeah if you're getting into it to just i mean i remember when um we were losing to clinton in the fall of 2007 right pretty badly and obama sort of gathered us all around and he said look i want to win this nomination i think i can be a better a good president i think i can be a better president than her but at the end of the day if I lose this I'll go back home to Chicago I'll raise my kids I have a wonderful wife and I'll be happy

and I'll live my life I don't need this for myself I just I think I would do a good job in it and because he had that attitude he was willing to be himself and say whatever he came to his mind and all that kind of stuff and i think that's why he won yeah you know and i think when you get so wrapped up in

worrying about every single thing you say and how it's going to be perceived then that's when you get in trouble because that's when you start looking phony that's the rubio problem that's the root that is that is who marco rubio is and is there a normal person in there is he's just he's so inside his own head he looks like one of those people who has been planning a run for presidency for decades and has laid every single piece in place and is constantly nervous that what he's saying is going to be perceived the wrong way or he's going to piss off this constituency or that or not get this Trump vote. You can see the anxiety when he's on stage at the debate

that the wheels are turning in his mind and he's just not sure what he's supposed to say next. I'm not positive what the debates are supposed to accomplish because it's a totally unnatural interaction. And somebody like Trump, who's a performer, he's such a better performer than anyone else who's on stage. And he's just blowing everyone away in these debates until they finally started coming back at him. But those first couple ones, he was just being a bully and it worked. Trump has realized what most candidates, including my old boss Barack Obama, never realized, which is that they

are complete performances, these debates. Yeah. Right? I mean, Obama was terrible in debates for a long time. He got better during the primary, the more he did them. And then he was obviously- Why was he terrible? He was-

Because he thought- He's just overthinking it? He thought they were on the level. Yeah. And he told us that. He goes, I thought that you'd get up there and you'd debate issues with other people. And it's pro-wrestling. And it's pro-wrestling. And it's pro-wrestling.

You're grabbing the mic and you're yelling at Stephanie McMahon and getting the crowd going. And the way that you're taught to answer a question in a debate is soundbite first, main message, and then you sort of go backwards. So it's not like you'd answer a real question where you'd build a logical argument a logical argument from beginning to end yeah which is what obama does he's a professor lawyer right uh in a debate you just you just yell scream you ignore the questions it's it's wwf that's why marco that's why you're losing it's like your opener that's why ted cruz is a liar okay here's my point on that but that's that's like trump the pundit again too right like his best moments of debate in his debate and the debates are when he just says what everyone on cable has been saying anyway. Like, you're at the end of the stage, Jeb, because you suck.

And that's one of the few defensible things about what Trump's done these last few months is the debates are ludicrous anyway. They are pro wrestling and everybody kind of danced around it. And Trump was the first one who was like, this is wrestling right i'm just gonna start insulting everyone and that's and that's how you win this yeah and it though his messages are basically like just these big black and white headline this that this you're a liar you're a jerk you're losing low energy you low energy and he's just and it's really tough like poor je Jeb Bush. He didn't know what to do. Well, Jeb is just, he looked like a candidate from another era. And someone had written this too, but the last time he had campaigned was a decade ago, maybe.

And so he'd been out of politics for so long that he didn't realize how much it had changed. And so he still thought that people were having debates like they used to back in the day. And he was so not prepared for what Trump was. Now, we're going to call Dan Pfeiffer, your old buddy. We're going to take a break to talk about our buddies at Betterment. If you're Danny Ainge, Celtics GM, the best way to invest in your future is trading two rapidly declining future Hall of Famers to a team with a crippling cap situation and no young talent. In exchange, you receive multiple unprotected first-round draft picks. That is investing in your future. For everyone else, the best way to manages a customized portfolio for each goal.

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Betterment, investing made better. All right, we're calling Dan. So if you had to bet who's gonna win the election right now, you'd bet Hillary? I'd bet Hillary. I think I would too. At this point, because it's Hillary and probably Trump or Cruz, Trump or Cruz, it's unbelievable.

The most hated man in Washington versus one of the most hated men in America. It's unbelievable. Are we sure Trump's not going to win? I feel pretty good now. There was a couple months where I was a little worried, but his approval ratings in the last couple, like, it's sort of hit a critical mass at this point, how bad he is. And I think his approval ratings nationally are dropping pretty fast. All right. But I don't think we should take him lightly. I mean, I've never been in that camp.

Is Dan on? He is. Hey, Bill. Hey, you're on with Dan on? He is. Hey, Bill. Hey, you're on with me and Favs. Hey, Pfeiffer. Perfect. We were just wondering if Trump could actually win. What is your take?

He can win, yeah. I mean, once you're on the ballot, anything can happen. And I would say he's probably, if it comes down to Trump and Cruz, Trump is more likely to win than Cruz is. I actually would agree with that. Me too. I think Cruz is unwinnable. Yeah. He's the least likable candidate to run for president in modern times.

My favorite was when he tried to hug his daughter that time and the daughter was just recoiling. At no point have I ever tried to hug my kids where they recoiled backwards. That kid was channeling the American people. The best story I heard about Cruz was when he was in college, in his dorm room, they had a poker game. And obviously it was illegal against the rules. And Cruz went down like $2 thousand dollars he owed that he didn't have so instead of paying what he owed to the rest of the people who were playing the poker game he went to the RA and told on everyone else that they were playing poker in the dorms

no yeah that's a true story a reporter told me that there so there is no way like this whole like the 1976 Republican convention when they basically decided it on the floor I mean that can happen in 2016 I think that's why

Rubio's staying in the race right yeah I think I think that's why he's staying in the race but I don't I think it's very hard

I think one of if it Trump and Cruz are very close in delegates and neither has a majority, they could give it to Cruz if they, which they will hate because the Republican establishment hates Cruz. Right. Almost as much as the rest of the American people. Yeah.

So I think if it, if it's not Trump or Cruz, it will be like some, you know, white knight and they will be white. Like Romney or Paul Ryan. Because it's hard to be like, hey, you were behind by a thousand delegates, Marco Rubio. Let's just give it to you.

That seems really hard to make. Yeah, Paul Ryan is actually, you know, you can bet on the Republican convention, obviously. Joe House and I lost on Rubio. We had him at like plus 650 and that fell apart. But Paul Ryan, there are odds for Paul Ryan, which I thought was interesting because he's not running. when Trump or Cruz have the most delegates but just didn't hit the number 1237, Trump supporters and Cruz supporters will burn Cleveland to the ground. I mean, that is very literal.

And Trump supporters, like there's been stories this week about it's kind of edging toward a little violent. Have you seen the video of the 70-year-old man who just sucker punched the protester on his way out of it yeah i mean there's like actual violence that happens there yeah there's no chance like america i mean is there i'm gonna rephrase is there a chance america might just lose its mind this summer during this whole thing yeah and maybe america has lost his mind and we're just figuring it out right now.

Because there's a counter to this that just says, hey, in 1964, everyone thought the Republican Party was going in the shitter and Goldwater got annihilated. And then four years later, Nixon. So I've never bought the narrative that this is it for the Republican Party and they're done and it's over and this is going to fall apart and it's a new world order. Four years from now, I might just be back with a different candidate. I totally agree with that. In 2005, right after Bush won, a couple of reporters wrote a book that was called The Emerging Republican Majority, how they win forever and Karl Roth had it all figured out.

And then the book came out one month before the Democrats swept the House and the Senate in 2006. So like every time we think that it's the end of a party, they find a way to figure it out somehow or find the right candidate and get lucky. I mean, if you had a Marco Rubio who didn't come across as so phony or a John Kasich who is just a little bit more charismatic, you'd have someone who could win the presidency. Maybe the answer is John Kasich should drink more before the debates. Maybe just have like one vodka tonic. Just needs to loosen up a tiny bit. Just a little more gregarious. He must be the only one who's not drinking at those debates.

I'm so convinced he like naps between questions because he always seems surprised every time they ask him. He's just like, oh, yeah, he's got like that weird bed head like he was asleep right before that maybe he's hibernating until the next question all right so let's say you guys are right out of college you're desperate for a job fab's just told a story i was working for like 20 grand um and the trump campaign targets both of you and now you're working for trump you needed a job it's a good break in the business what do you guys do to try to get trump to actually win this election what would you tell him if he just looked at you and was like i trust you guys i want you guys to help me win this election what would you tell him i mean i look i i i did this uh horrible fantasy

a couple weeks ago i wrote a um i wrote a pretend Trump speech for the Daily Beast. Oh, God. I think his his core message of, you know, economic populism tinged with some nationalism. Right. Is has brought on a lot of supporters. Right. Like that's why he is where he is. I think that all of the overt racism and bigotry yeah and the not not tamping down the violence and the saying crazy shit and the the you know dick measuring stuff like i don't think that's helping him like i think that gets him

news cycles but i think if he really wants to get a news cycle there's a way to do it and be flamboyant without quite going as far as he's going you know so i think i think if you're in that campaign i mean you could actually see this last night in the debate he they called it the civil debate even though it was almost just as bad shit crazy as the others yeah um but he he toned it down a little bit because i think he knew that he had gone too far in the prior debate and that it was probably hurting him in the polls. What do you think, Dan? Well, I think he should, I mean, one thing is like psychological warfare.

The way he wins is, if he's running against Hillary Clinton, is that like Obama's voters do not turn out, right? Because these are people who have really only voted when Obama was on the ballot and didn't turn out in midterm elections, were either not too young to vote or didn't get involved with Kerry. And so he just needs to make Hillary Clinton seem so lame and boring that they're not going to turn out. And bringing up all, which I think he's going to do this, which is like bringing up all the i think he's going to do this which is like bringing up all the old stuff um from the clinton years will be part of that and i do think that if he uh he will be most

candidates when they either run to the right or left in the primary and then it's really hard to move back to the middle because you you know you change your position the press kills you for it and the interest groups on your side come back and say wait you told us this trump just doesn't give a shit like he doesn't care if politifact gives him like like 7 000 you know bad fact checks or whatever else he probably he just goes out completely pivots on immigration and seems less scary and then just like gets inside hill inside Hillary Clinton's head the rest of the time, he has a shot. I mean, it may be the demographics make it impossible, but the thing is, we all say Trump can't win,

but all the same people who say Trump can't win the general election are the same ones who said he couldn't win the primary. So who really knows? He has one message against Hillary Clinton that he already has delivered a couple weeks ago. She's been there forever. She hasn't fixed anything.

Why would you put her in there to fix things now? Yeah, and it does seem like— It's actually not that radical. Yeah, and if he basically said, hey, the last 25 years or 30 years, this country's been run by Bushes and Clintons and Obama's an extension of the Clintons and it's time for a change I think that would resonate and I know this I used to take money from them and then I owned them

and they had to come to my wedding because I gave them money and that's the kind of relationship I had that's the kind of people they are that's what he's going to say he also does this really devious thing where he just makes these accusations of implication where he's like, and I'll be the one who beats Hillary Clinton if she can run. I mean, I don't even know, given all the illegal stuff she did.

She may not even be eligible. Who knows? Oh, yeah. Right. It's so good. Well, he already has this set up, too, because he's going to say that if nothing comes of this email investigation well obama's justice department protected her otherwise she would have been indicted and in

jail yeah that's gonna be that's that's gonna be the when hillary wins the presidency the new way to delegitimize her as president just like they delegitimized obama it's interesting that this was the direct this was the election where everybody thought oh we figured out with advanced metrics and all this stuff. We know who's going to win every primary. We know who has a chance. We know who doesn't. And then 2016 comes along and throws that completely out of whack.

Like 538 was saying Trump had no chance and his support was going to fall apart as people kept dropping out. The opposite happened. Everybody thought Clinton had Michigan locked up. It was a 99% chance. Sanders wins. My thing is, like, I don't even know if you can apply math to 2016. Just throw it out. It's too crazy.

This is like the equivalent of if you just found, like, five guys on a playground and threw them in the NBA and they beat the Golden State Warriors. Like, it makes no sense right like we all think we're like such experts and like we look at data and we have these complicated messaging and communication and social media strategies and some guy who just like phones into a lot of cable shows and tweets out insane things it's like cleaning everyone's clock and like it makes you wonder like how valuable is all the stuff that campaigns have you know spent all this money on really is but doesn't it doesn't it make sense after the fact dan too it's like no one could predict it but now that

it's happened you look and you're like how did we miss this of course trump does well yeah right like in this country in this media environment yeah Yeah, but I just thought some of the things he said were so horrible that that would be it. You know, you think like when the bridge thing happened to Chris Christie, everybody was like, that's it. He can't win the election now. That's too big of a scandal. And Trump's done like 20 things like that or said 20 things like that that had the same kind of impact. And nobody, it just bounces off people. Think about that.

Imagine if Trump was in Christieie's position on bridge gate trump would have come out and been like yeah yeah we had all kinds of corruption that's how i that's how i do things as governor that's how i make money like we just had to get stuff done who cares right i'm sorry i'll take accountability for that yeah yeah those people had to weigh on the bridge they couldn't get to school i don't care whatever what would you guys tell i mean sanders is still in this yeah you're working for sanders what would be the tactics for that for trying to win the uh the nomination oh man this is a tough this is a tough one because he's he's in it but the math at this point is almost making it impossible like you get to a point with the

delegates where like for Sanders to get the nomination, I don't know what percentage of the delegates would he have to win from here on out? Like a hundred? It's like 70%, I think. I mean, he's basically not mathematically eliminated, but he's like one game away from being mathematically eliminated. I mean, the best thing for Sanders to do is like if he, you know, I mean, one option would be to drop out of the New York City Clinton, but it seems unlikely he's going to do that, is just keep winning as many delegates as possible.

And even if you're not going to win and get the nomination, you know, he will at least, you know, can carry, you know, his message and, you know, try to drive the policy agenda. Maybe he gets lucky and something happens. But he's basically mathematically eliminated, but what he's done is pretty impressive, given that he's a guy who's basically run in Vermont a couple times, and that's it. He's taken Hillary Clinton, not to the wire, but made her work for it a lot more than

anyone would have thought. Is there a scenario where she doesn't get the delegates either? I don't think so. so yeah it seems like she's getting them she's getting it so he's just he's kind of hanging around and waiting for another clinton scandal to come out of nowhere basically yeah i think so yeah clinton kind of did that to obama like we got to a point where in a way where we basically had the delegates and there's no way she could have caught us and she just kind of hung around for another six weeks, you know, thinking that something would happen. And maybe she'd get a last shot at it.

It's the greatest six weeks of our lives. We thought at one point, it was like some point in April, we woke up thinking like, we are going to spend the rest of our lives running against Hillary Clinton in this primary. And nothing is ever going to change. This is this is now purgatory. I remember that it was like interminably long where people were like, she should drop out now. Don't really. She should drop out. Now it's time you should drop out.

Isn't it weird that you ended up working with her, though? Yeah, it was bizarre. Yeah, that was what when he when he selected her as secretary of state, it was one of the more surprising moments. I like I couldn't believe it. But then it made sense. When he selected her as Secretary of State, it was one of the more surprising moments. I couldn't believe it. But then it made sense. I thought someone was bullshitting me. Me too.

We were in the transition and these crappy offices in downtown D.C. And we're trying to find an Interior Secretary, the Undersecretary for this. And a reporter calls and says, we hear that Obama's considering Hillary to be Secretary of State. And I was like, well, I'll check that out, but that can't possibly be true. It was like, it seemed insane at the time, but it ended up being, in addition to the fact that she was a great Secretary of State,

so it was the right decision for that, it was like our lives were very different, that she was working with us instead of on the outside with everyday people going, is Hillary Clinton going to primary Barack Obama in 2012? You know, is she going to challenge him? Like, that would have been a political nightmare. And everyone thinks she was a very good Secretary of State, right? Nobody, is there a counter-argument to that? No, there were no, there were no, secret battles in the white house or resentment or anything

like that. It was, it's all real. And it seems like Obama has genuinely enjoyed working with her for the most part. Yeah, he definitely got, they got close. Like you spend a lot of time with secretary of state cause they travel with you around the world. So like when we, we go on these like 10 day two week foreign trips, she's there every day on the plane with us sometimes and so you just spend a lot of time and they had a secretary of state has like a weekly one-on-one meeting and i think there's no doubt

that it was a little tense at first you know they kind of like were figuring the whole thing out because you know like you go through a campaign like that, and you build up a lot of, like, anger and competitiveness. But after a while, they, you know, he was very, like, super appreciative of her and very, like, nostalgic when she left in early 2013. I mean, they're both policy wonks, and they both view the game of politics as bullshit yeah right like it's in it and in that way they're both different than bill clinton like bill clinton sort of loves politics he loves the game he's in it he's fine and obama and hillary both sort of have this ironic

detachment from it and and think that it's silly and sort of feel like you have to play it to get your agenda passed and i feel like they bonded over that a little bit. How many times during those first four years with Obama did he be like, come outside, let's talk. I'm going to have a cig in the Rose Garden. Come outside with me and let's talk about this. Never seen it. Never seen it?

Never. Everyone's sworn to secrecy. He claimed he hasn't smoked for like the last four or five years. I think that's right. Yeah, I believe that. I'm amazed that his wife let him smoke because it does seem like she wears a lot of the pants in the family. I don't think there was any letting. Yeah.

So he was sneaking around. In eight years of working for the guy, I never saw him smoke one. Which didn't mean he didn't do it, but I never saw it. That's the thing with that, when people, especially as we head to the home stretcher of the Obama presidency, and nobody is going to really talk about the first lady transition. Oh, yeah. But there's, you know, it's not a good chance, but it's not out of the question that we're going to go from Michelle Obama to Melania. Who Trump was on Howard Stern talking about the incredible size of her bowel movements.

It's an actual conversation with them on Howard Stern. You can't believe how big these are. Coming soon, America 2017. But Michelle was like, what does she do where does she go what happens to her she did that i asked obama does she does she do a daytime talk show like i can see anything with her i can't see her taking a very public role yeah um just because i think you know she really loves her friends. She loves her. I think she misses her private life. Like, I don't think that she's looking to go out there and and be out in public a ton. I don't know. That's my sense. She could surprise

us. What do you think, Dan? I think I think she'll probably like there's a handful issues that she works on in the White House. I think she'll continue in whatever sort of post-presidency life they have together. She's such an interesting figure because, like, most people who end up in the White House, President and First Lady, like, spend decades getting there, right? They were, like, pretty normal people. Like, he was a state senator in Illinois, and she was a, you know, she worked in Chicago as an attorney. And then, like, all of a sudden, the president and she was, you know, she worked in Chicago as an attorney. And then like all of a sudden the president gives a speech at the convention and then they're famous.

And then like two years later, they've moved into the White House. It's like they they really got like teleported out of their life, which they expected to be a fairly normal, good life in Chicago. And all of a sudden you're a first lady. And it's just such a different experience. I think she will probably, and he will as well, to the extent possible, be kind of glad to get to as close back to what the life was like before that as possible. I want to talk about Obama's future, but first I want to talk about Slack, which is the unofficially official messaging app for The Ringer. So when you guys were in the White House. Also for Fenway Strategies.

It's the best. Slack is the best. When you guys are in the White House, you're just exchanging all these emails and there's like giant, what, 100 email chains you're trying to figure out. Our whole staff uses Slack. We put in our newsletter with it. We put in our website with it.

We put in our podcasting feature with it. We make fun of Tate. Tate, the producer, we make fun of him. It's a messaging app for teams instead of searching through hundreds of emails and texts. Slack brings your work communication into one place and radically increases transparency between teams. You felt that, Favs. The transparency radically increases. Your disjointed conversations will no longer be disjointed.

They become jointed and uh and your internal emails will be cut down by almost 50 they also have nearly 100 integrations including dropbox mailchimp and google drive visit slack.com slash bill simmons and create a new team you've got a hundred dollars in credit you can use when you decide to upgrade to a paid plan slack.com uh we really like it my my whole thing with emails i get so many emails and i'm on so many different chains it's just a pain in the ass to figure out where i am and slack i just go and there's the category and we go dan let's move our chain to slack yeah move your chain to slack do a private chain they have the private thing i've noticed that yeah we have a little family private thing it's good uh all right

obama's future. So what happens to him next year? What's he doing? What are the... After Hillary nominates him to the Supreme Court. Ooh. I gotta give you credit. When I did the GQ thing, you told me to ask him that. And it was the only time I really...

I legitimately rattled him. I'm glad we did that. I figured it might rattle him. For like a split second. You just got Fabs in trouble with the White House Press Office. I was like, hey, what should I, should I? And you were like, well, maybe ask him about this. I've never heard him talk about it. I hadn't.

You didn't have inside info. I was curious as a citizen. Yeah. And he paused and he hesitated and then went into like Obama. Although reading what he said to you and knowing him, I could tell why he paused. And I don't think it was because he was thinking, oh, maybe I'll be on the Supreme Court. It's what he wanted to say was, of course not. I don't want to do that. But he didn't want to denigrate being on the Supreme Court.

Oh, that was your takeaway? That was my takeaway because what he said to you next was like, like well i have to think about this because it is such an important job and it's you know and it's important to the country and blah blah so i think he didn't want to trash the supreme court as a job but i think he wanted to tell you but that's not for me you know because yeah that's a lot of just work and a lot of writing and writing and i don't think he liked i don't think he wants to do that. No. I think he's going to be in Hawaii in the Magnum PI house.

Just driving around a convertible. What do you think he's going to do, Dan? Look, he's going to write a book for sure. And I think he will try very hard to write a book that's different than the typical post-presidential memoir. Because he does still think of himself as a writer. And like when he meets with writers, like he thinks he's bonding with them like on a author level.

I think there are things that interest him that I can see him, like he'll have an array of, you know, things like the My Brother's Keeper initiative for, you initiative for young men of color and some other things he's doing. The White House, I'm sure he'll do. But the things that are very interesting to him are sports, the whole media world and how people communicate. I could see him getting involved in that in some way. There are some things that when you're killing time on a plane or something, you just start talking. He's got like a lot of, there's some things that when you just start, like you're killing time, like on a plane or something, you just start talking.

He has like deep thoughts on it. Like the media ecosystem and how people think is like very interesting to him. Yeah. That was the one I ran out of time because he,

he was definitely filibustered in the first 25 minutes. It took me a while to get him moving. But I really wanted to ask him if you could change like three things about the media culture with politics. What would be the three things? How do we make the media culture better with politics?

You would have had a filibuster there for sure. Yeah, he wouldn't have answered it. How would you guys have changed it having been through it? Dan, you go first since you're the communications director. What's the biggest flaw in the system right now? I think the biggest flaw in the system is probably we confuse reporting and analysis now because of Twitter, right? So everyone is an analyst always. And that's somewhat dangerous.

There's not a place where people can go to get a lot of like just straight reporting yeah and so it's like it used to be pre-twitter right there was this very fine line where you're you know you were either the reporter or the columnist or you were the or if you were like the big time political reporter you got to write an analysis column on sunday and so there's right now it's just like all the people who would just be writing a story about what politician A said today are also providing analysis and don't necessarily always have

like the background or perspective to do that. And that confuses, I think, it makes it very hard for people to just like find out what actually happened today, that day, as opposed to like what it means for the horse race and the poll numbers and all of that. That's basically what's happened in sports. Yeah.

There's no delineation now between somebody reporting something or somebody that thinks something might happen. I've done it too. I'm like, hey, I'm hearing this. I'm not reporting it. It's just, hey, this is scuttlebutt that's floating around. My personal take is I think the decision with LeBron James was like the seminal moment for sports reporting. That was the first time people were just throwing shit out. Right. Hey, I'm hearing the Knicks.

And we're like, oh. And then it'd be like four hours on ESPN, people talking about that. When do you think that happened in politics? It was somewhere during the Obama presidency, but I'm not sure where. I think it was when reporters got on Twitter. Yeah. So you think it was like 09 probably. So it was after the campaign,

because Twitter didn't take off until 09. Dan, don't you think it was when Politico started in 2008? Well, Politico definitely changed, brought sort of like this ESPN mentality to sports, where they're going to cover the game, not the substance. And most press probably cover the game too much. And, but they wrap themselves in this like glory of the fourth estate. If we cover substance and we're going to educate the people and Politico was kind of like, F that there's some audience of people who care just

about the sport of politics. And we're going to really dig into that. But I think once you got to Twitter, like for a regular reporter at The Washington Post and New York Times, there was an editor who would delineate whether something was analysis or had to meet some set of thresholds before you could report it. And on Twitter, it's just people can just throw it out there all the time. And I don't even think the press has really caught up to this, that like what you say on Twitter is probably more important than what you actually say in the paper. But the paper is all these like controls in place to keep you from doing, you know, crazy things or analysis you're not qualified for. But Twitter, it's just like whatever you're thinking at that moment, you know, fire away. I think that the speed of everything has also sort of eliminated a sense of perspective and a sense of history.

So, like, we now don't, I mean, everything that happens each day seems new and crazy and, oh, it's the weirdest thing that's ever happened. But then you don't, I mean, like, there was also violence and craziness at the McCain-Palin rallies in 2008. People were getting beat up and calling Barack Obama a terrorist and yelling treason and stuff like that. So it's just like, we forget certain things now, because everything moves so fast that we don't have a sense of what's happened before. And that sort of warps our judgment and warps the analysis, too. When you guys went through the reelection campaign in 2012, what was the biggest difference you noticed from 2008? Other than that, you had the leading candidate, obviously. Yeah, well, the tough part was, I mean, we were also on the other side of the message, right?

There was we were we were the incumbent, not the person saying it's time to change. Right. Right. And so that necessarily meant that we needed more of a contrast, right? That this is a choice between two visions. This isn't, that's not working, so try something new. I think that was the biggest, from the message perspective, that was the toughest part. What do you think, Dan? I think two things.

One, like, the first election campaign is always like this glorious cause and everyone's excited and re-elections are always just like a grind like you were just you know it's it's by nature less inspirational and exciting like from the you know how you deal with the media like you know i don't want to keep harping on twitter but twitter we didn't use in 2008 in any way in 2012 like entire parts of the campaign were being litigated on Twitter 24-7. Even in the first debate when Obama had a less than stellar performance, to say the least, had Twitter not... The way that would have played out pre-Twitter is there would have been some stories saying he didn't do well the next day,

and maybe a poll came out that said he didn't do well. But middle of the debate on twitter you know another important thing i remember is like reporters used to just watch the debate all by themselves and not have any sense of how the rest of the world was reacting to it and so they'd make their own analysis they're all on twitter and so like when andrew sullivan and chris matthews basically committed ritual suicide over how bad obama's um was, everyone reacted to that. And it took what was a bad performance and made it seem like the end of the world. And so that, like, the instant reaction shaping things before they actually happened, I think

fundamentally changed how campaigns and probably, you know, maybe all entities sort of trying to push for something how they have to do what their strategy has to be i noticed this from a speech writing perspective too like 2007 2008 obama would deliver these like primary night speeches and there was an analysis live analysis going on during his speeches so everyone would take it in look at the audience look at him and say okay that was a good speech or bad speech, whatever. Now, when someone gives a speech, there's Twitter commentary during the speech and it's all cynical. And so it's that much tougher for someone to, for anyone to deliver a speech or deliver any kind of public statement that's impactful,

conspiring, that moves people because people just start tearing it down word by word on Twitter. I think that's starting to fade a little bit. I mean, I think people are burned out from the cynicism and the snark and all that stuff. But where you see Twitter really jump in, well, a couple of things. One is like when you have like the penis moment with Rubio and Trump. And that just, you know, I didn't watch that live. And I checked my feed to see more what was going on with NBA than anything it was just a stream of penis tweets for like 15 minutes I was

like what the hell just happened I thought he pulled it out did he pull it out that's next week and that's actually like the great thing about Trump's campaign is that part of me wondered if he pulled his dick out in the debate it was not surprising i was like i wouldn't have been blown away by this but i do think people on twitter follow mostly people who agree with how they think so it's this group consensus think and if it's going one way or the other and everybody is reinforcing what you thought it almost makes it worse i don't think people fall especially in politics you don't follow everybody from all different things. In sports, you do. I'm following Laker fans. I'm following Knicks fans.

I'm following Heat fans. It doesn't really matter. In politics, it does. I follow a lot of Republicans and conservatives and conservative media. But you're abnormal, though. I mean, you're a student of the whole culture. I think most people just follow people that are like them.

I think that's probably true. Do you hate follow the people people that are like them you know i think that's probably you probably do you hate follow some people yeah i've tried to hate follow fewer people okay because it was getting my blood pressure going dan who do you hate follow oh you don't have to answer i unhate like there's everyone when i left the white house that i had to follow for my job yeah really annoyed. I either unfollowed or muted. Like, I'm retired now. Why do I need to spike my blood pressure? Because Ron Fortier is criticizing Barack Obama's leadership. Right.

So Politico, they do this stuff where they write the headlines a certain way when it's not really what somebody said, but... Just to get the clicks. To get the clicks. That happened to me yesterday. Business Insider. What did they say? They did the Simmons declares war on ESPN. said but just to get the clicks to get the clicks that happened to me yesterday business insider what did they say they did the simmons declares war on espn all right i said in a podcast yesterday joe house asked me why brian if i could have brian windhorst on and i said no actually

this is so annoying espn won't let espn people on including people that i'm friends with and it's like oh i'll get them back i'm gonna hire a public editor to write about espn where you know it was humorous and then it's like businesses are simmons declares war on espn it's like oh my god i can't win well i mean and in fairness to politico they might have started that trend but that's yeah that's everywhere now no that's the sports the sports blogs and the regular blogs and all kinds of different things yeah you write a headline a certain way and you try to get people to click on it. I get it. The problem is so many people aren't clicking because they don't have the time.

So a lot of people are just getting their news from headlines. Right. Right? So you can imagine what that does to people, right? Yeah, yeah, yeah. Sometimes people only get their news from headlines or the chyron on CNN. And that is super dangerous because it's unbelievably like just wrong. Most of the time. I got the feeling for even just from spending an hour with Obama and then like,

you know, five or six shooting the shit minutes after it seems like he's about done with all this. He's just ready. It's ready to move on. Ready to, to get out of this whole cycle of the way things work. I,

in some ways, I mean, I think he's, I think he'll always be interested in it though. Like, I think he wants to take a break, right? I think he wants to step back and take it, but I don't think he'll be, I think it'll be harder for him to cut off, cut all this off than he thinks. Because like you said, once you get him going, once you get him talking about some of this

stuff, whether it's politics or media, whatever, like he gets very passionate about it. And Dan, you, you you you know this more than anyone he used to love when people would come visit when the teams came the championship teams like that's probably the part that's probably that's got to be the most fun part of the job and that's the stuff like once you're not present the presidential dinner trying to be i mean he's probably the funniest president we've ever had the first president who's been able to go on the dais and actually make funny jokes. He's an above average comic president. His delivery is quite good.

Yeah, really good. Yeah, like he always, I mean, we all come up with jokes and we have outside comedians that send in stuff. But almost every year at the Correspondents Dinner, his delivery has made the jokes funnier. Yeah. We'll just wait until next year with President Trump. People storming out. This is terrible. I'd like to introduce our host, Andrew Dice Clay.

Dan, when did you leave? A year ago, basically leave in a year ago basically like a year ago this week and what what were the first like six weeks like I got on a plane

and I flew to Asia and traveled around for six weeks and did not like read a newspaper paid no attention to what was happening

and it was like pure bliss did they have Asia Politico there or no if they did I couldn't read it and when did you leave fabs like 2013 march of 2013 yeah and we i i left and and tommy vitor and i started our our business right

away and bench wearing right fenway strategies yeah and you eventually moved here and then i moved here about a year later yeah the the year living in washington where i wasn't working in the white house was that was when it was a signal, it's time to get out of here. Well, you guys were kind of, for lack of a better word, local celebrities. People would write about you and you'd be at a bar. Not always in a good way. Not always in a good way. You were covered to some degree because you were the young kind of people in Obama's cabinet.

Yeah, which is a very washington thing right it's like at some point i mean i i love my time in dc i was there for 10 years but uh except for the couple years i spent in chicago but when i left it it was time to leave because it's a very small city it's like boston it feels like high school it's very small and very gossipy and everyone knows what everyone else's business is yeah it's like it's but it's like if boston was a company town yeah right if everyone worked in the same industry yeah and that's what washington is so you can only you can only handle that for so long where'd you guys live in washington uh i was at 16th and r so that was like between logan and dupont circles but that was pre-Uber, though. Last couple years, yeah, Uber.

Uber could have been bad for both of you guys. Uber's like, I'll have one more. I'm not driving. We could walk a lot of places. That's what we walked all the way. It's a walking city. So it sounds like you miss it, but you don't miss it. I don't miss it.

I miss my friends who are still there, but I don't miss anything else about it. You miss the... I thought, like, there's sort of two paths for people who leave the white house. Like one is you go into like depression, you know, you're just like, why am I no longer important? Why is no one emailing me? Right. Like, you know, why, you know, no one recognizes me on the street anymore. And then the other one is like, oh, there's's this whole world out here like of a life and sleep and friends and family and i was pretty convinced i would be on the depressed side and it was the exact opposite like i miss the people but there's not has really hasn't been a moment where i was like man i really wish i was there for that even the good thing because when you've been inside you like you know like today the supreme court like validated health care everyone i knew out here in francisco was like don't you wish you were there don't you wish you were there and i was like no i remember the 1000 meetings that would have led to just like that moment like i was pretty glad to like sleep in and see friends and

you know like it's a great experience when you come to a moment when you're like the key is to leave like one day before you're burned out right did you see that with some people that you you knew they stayed like six seven months too long and you could kind of see they were fried totally yeah sometimes they want to leave but the president wouldn't let them because they were in the middle of something that was like important or like they were trying to pass health like they were going to be there until we passed health care or something else. And that just went, like, six months or a year longer. And they're just, like, dragging. And it's easier for people like Fabs and I because we don't have kids.

For the people with kids, it's brutal, right? Like, they don't see their children. They don't, you know, they have to miss stuff all the time. If they get out and get to, like, the soccer game or whatever else, they're on their Blackberry the entire time. It's pretty hard. But it was also like the president would always say it's a family-friendly White House. Yeah. And my thing was I was not going to have a family to be friendly to if I stayed there any longer.

Because all my 20s were campaigns and politics and White House. And it's like at some point you have to have a real relationship and grow up and get a family and um you can't it's hard to do that when you're in that job what was the lowest moment when you were there where you just felt like the just everybody that worked for them were just collectively bummed out devastated or just depressed the one that comes to mind that was early on was the oil spill. Right. The oil spill, because it was sort of like the first crisis that happened to us that we could not control. And the president had every engineer and scientist all over the world trying to fix this thing and couldn't. And so in the corner of every cable news station every day for 30 days was a picture of this oil spilling out into the Gulf of Mexico.

And people were saying it's the end of Obama's presidency. He can't do anything about it. This is his Katrina. He's Jimmy Carter. And sort of the first time in the way, like you realize, hmm, maybe this isn't going to go so well. What about you, Dan? It was the day that Scott Brown won the Massachusetts Senate seat, because we had basically, health care was ready to go, we were going to get it passed, and then we lost a Ted Kennedy Senate seat,

which meant we were going to have to basically start all over again. I remember like, we all sort of like sheepishly walked into the Oval Office the day afterwards. And, you know, the president was clearly displeased because like, basically he had fought so hard to get healthcare. And then like, if a Democrat came with a Massachusetts Senate seat, like, what are we doing? Right. And he kind of like, we go through like our daily advisors meeting

with him and after a while he kind of looks at us and he's like not really you can tell he's got that look of like i'm not going to yell at you but i'm pretty annoyed about this and he says he finally like looks at us and says you know why don't we do this like why don't i try to you know fix the economy figure out what we're doing in Iraq and Afghanistan, pass health care. Can someone else be in charge of winning the Massachusetts Senate race? And kind of like got up and walked out. And we're like, yeah, that was a mistake.

I mean, in retrospect, could you have delivered the message better in a smarter way to the public, just like how hard it is to do that job when when you're a democrat and the republicans have control of so many other things do you feel like that message was delivered well enough obama would certainly say there was a better way to deliver it yeah but what's the what's the way though because you don't want to sound like you're whining the whole time right so there's got to be some balance between hey man i'm doing the best i can versus i can't get anything yeah because well this is why it's so hard it's like you can complain about the opposition but then it sounds like you're complaining about the opposition right and they

sort of knew that that was their strategy right they're like if we deny him any bipartisan cooperation whatsoever then all of his promises that brought him to office about being bipartisan will look phony. Right. And that's all we have to do. We just have to keep saying no. Right. There's no question, like, we could have, our message, or should I figure out on healthcare

or things like that, our message could have been, like, tighter and we could have been more disciplined about it. And there were certainly more clever ways to deliver it in a more targeted way to, like, get through the, you know, White House press corps filter and all of that. But sometimes, like, it's not, like, the bigger thing is not, like, not your communication strategy. It's the fact that there's, like, 10% unemployment in the country. Like, we don't have, there's not some secret plan to make people feel better about that. But like, you know, it's interesting that like, we, like Obama's time in the White House, like, dovetails with, you know, as media and the internet and everything is changing in

this dramatic way. And like, you know, we try to stay at that curve as much as possible. Sometimes we're ahead of him, sometimes you fall behind. And like, you, you know, the old ways of doing things just are the sudden inoperative and you didn't really sort of get it like when he started running for president like the iphone didn't exist facebook was barely around like as you point out twitter's not around and so you look at where like how people you know how journalism is and how the people learn information now compared to when he started like it's been it's probably like the greatest period of change since like telegraph or something i totally agree and i and i said this to him i think people are

going to remember him as the social media president not him but just that was the presidency when in 2008 as you said no ipad barely twitter no instagram facebook was for kids adults really weren't using it that much yet. No Snapchat, all this stuff. And now we're a tech, we're the technology society. And it all happened during his presidency. I think Dan realized when he was communications director that at some point the traditional media filters are broken. They've broken down.

They're covering analysis and all that kind of stuff. And so you just try to find ways to go around them, right? Whether it's Facebook or Twitter or any of these other interviews that the president has done. And, you know, like maybe we could have done that earlier in the presidency, but I don't even know if they existed then. Yeah, it was 2009, 2010. So you just couldn't do it. But I mean, if you look at Trump's candidacy now, the networks and the media can say all they want about Trump, but Trump has however many millions of followers on Twitter and Facebook, and he just communicates directly with them that way. Yeah.

You know, and I think future presidents and future candidates are going to use, are going to go around the media to communicate directly to voters. Yeah. Like Facebook's pushing their, their Facebook live so hard right now. What would stop one of these candidates from just doing a Facebook Live interaction with whatever?

And the press will go nuts. Oh, it'll go crazy. But it'd actually be a really smart move. It'd be a good move for Rubio because he could make the camera grainy. You won't see how sweaty he is, how much water he needs. All right, we got to wrap up.

So give me a prediction. So it sounds like you guys think Trump versus Clinton, we're headed toward that, unless something crazy happens on the floor of the Republican convention. I will say Trump versus Clinton. I'd be more sure of that after Tuesday. Because I think if Trump wins Florida on Tuesday, then I think it's very hard. It's a wrap. I think it's a wrap. What do you think, Dan?

I think that's right. I It's a wrap. I think it's a wrap. What do you think, Dan? I think that's right. I think the most likely scenario is Trump. I think it's by far the most likely scenario. If he loses Florida, Ohio, or both, the chances of a House of Cards style contested convention

will go way up. I think Clinton wins, obviously. I think it comes down to the convention and i don't i don't think we know i could see somebody who's not running right now win i would vote for that over trump winning i mean just like for as a prediction the white night it might not even be a white night it just might be somebody dressed like a knight but i just think it's i think we're gonna go to that convention and i think it's gonna be one of the craziest i don't know it'll be all stay away from cleveland

in july have you have you watched like the uh it would be a really good documentary actually the the 76 one i've seen some clips recently because it was cordial but it wasn't cordial and then it got nasty but then it was kind of cordial near the end. And, you know, finally they settled on Ford. Well, the one that's going to look more like could be 68 in Chicago, the Democratic Convention, which sort of erupted into violence. Yeah, that wasn't great. That was not great. I doubt we had a worst case scenario.

That's bad. But that's... The way these people are at these rallies right now, that's what I'm more scared of. All right. You can follow Jon Favs, J-O-N-F-A-V-S, at Twitter. And Dan Pfeiffer, that's your whole name on Twitter, right? Yep. Okay.

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see me again rewind this track right here close your eyes and picture me rollin'