Meet Democrats' Go-To Trump Stand In

0:28Hey, everybody. We don't want to leave you high and dry and contentless while we're on break. When I first worked for Hillary Clinton, he had a lot of fascinating insights that came from playing Trump that are just great stories, but also really helpful for thinking about how we continue to, you know, try to beat him. So here's a preview of that conversation. And if you want to hear the full episode and get a lot more great stuff, subscribe to Friends of the Pod at cricket.com slash friends. Here's Philippe. When I was 23 years old, I was inexplicably and incorrectly hired to be a speechwriter for Hillary Clinton.

0:58and I shared an office with who at the time to me was a grizzled veteran, but who was just a young man who barely spoke or made eye contact with me. He is a longtime advisor to Hillary Clinton. He also has a legendary role in two debate prep seasons. He played Donald Trump with both Hillary Clinton and Kamala Harris, longtime communications advisor and staffer to Hillary Clinton, Philippe Reines. Welcome. Hi, Jonathan Lovett. How are you? Good to see you. I want to talk about debate prep, which is the ostensible reason we're here. But first, I want to talk about your first impression of me. Well, I didn't think, it might have been inexplicable, but it quickly became clear that it was correct.

1:42I mean, you were talented. You had, your work ethic was similar to mine, which people can take of that what they want, whether it was high or low. We sat in a room with six people and we probably had, we were not type A's. We were probably more in the lower end of productivity. So I think we had kindred spirits on that. I could see your screen because of the way we sat. But no, you fit right in. You really didn't talk to me for like six months. You do know that, right? Like there were six of us in that room and you barely, you had the corner. I'm surprised it was only six months. That's short.

2:22That's short. But look at us now. Look at us now. All right. So let's talk about debate prep. How did it come to be your job to play Trump with Hillary? Who thought that was a good idea? So it was Megan Rooney, who you know. Megan Rooney is a longtime speechwriter for not just Hillary, but she worked in the White House for, most recently, President Biden, for President Obama, some for Mrs. Obama. She's, you know, everyone of name in the last 10 years, 15 years. And she, at some point early 2016, said, you know what you should do? You'd be good for to play Trump in debate prep. And I said, you know what?

3:03That would you're not crazy. And she said, you've been practicing your fact practicing for this your whole life. You just didn't know it, which was, you know, accurate, but backhanded. Why? Why? Why did that mean? Why have you been practicing? That I had just had a Trump in me that hadn't been released yet. But see, this is the thing that's so interesting. I agree with that, but I don't know why. What is it? You, there's something, you're not like Trump at all interpersonally, but there is something about you, like a feral understanding of media. There's something, there's something, there's a brokenness to you that explains why you're naturally suited to Trump.

3:40So what is it? So the closest I've ever come is someone said that they thought I had eye to tech aspects. Usually it's meant as it's associated with photographic memory. That's not what it is. But it also can often be you're able to assume the perspective of someone, no matter how horrible it is, like a FBI criminal behaviorist kind of thing. I think there's a little bit of that. But I wouldn't be as good playing Mitt Romney. I couldn't pretend to be a policy guy. There is something about... And the reason why it made so much sense with Hillary is because she was just innately bothered by my presence, no matter the circumstance.

4:26So I really just had to show up and she would already be her. That is true. There is something about you that that you're so you're indispensable and yet your presence does irritate her. That's such an interesting part of your dynamic over a long time was true when I was there. You also kind of have, I think there's something about the way in which you understand, have a love for kind of tabloid media. And also you like kind of, you appreciate and loathe journalism at the same time, just from having been a communications person for a long time. Like there, and you're a creature of New York media too.

5:00There is a way in which you were prepping for this. Yeah, I mean, I don't think anyone likes their press person. Because it's not like you walk in and said, oh, I have a dozen roses to deliver to you. You come in and you're like, oh, someone saw that you didn't leave a tip on a bill. It's never good news. Plus, I at times enjoyed kind of needling her, being irreverent, which you're not paid much on the Hill. So you need to get your entertainment where you can. But yeah, you are used to, it's an adversarial job. You find yourself, if not yelling, then yelling at Jason. And that's not too far from what Trump was in 2015.

5:46So talk about PrEP. What are you doing both to know what he'd say and to inhabit the job? So it was a little different. So in 2015, if you remember, he actually participated in the primary debates. And there were, I think, 12 of them. He went to 11 once he boycotted. I don't remember why. So there was a tremendous amount of material to watch. I watched each one three times. Once, just watched the whole thing. Second time, I watched just him, whether it was him speaking or him being spoken to. And the third time I did it with the microphone, with the audio off, just to watch the gesticulations and the facial features.

6:31And it was a treasure trove. And it was the first thing that stood out, and I think it even 10 years later stands out, is that his language was very unique. You watch him, and obviously he's not exactly a thespian. but because he says something so plainly or whatever you want to describe it there it came across as honesty if you look at word clouds from 2016 the two that people walked away from describing trump more than anything were honesty and strength and obviously he's the world's biggest liar but the honesty came from just speaking plainly and when you're on stage with nine people and almost all of them are either sitting public figures in the Senate or governors or past, they all have that stilted speech.

7:21So they would say, the moderator would say, Mr. Trump, I'm going to start with you. Why did you say this crazy thing yesterday? And he would say, it wasn't crazy. I'm 100 % right. You know what? I could have even said it worse. They would say, okay, Mr. Trump, we now go to Senator Rubio. Senator Rubio, tell us about your plan for immigration. Well, I want to thank the University of Wisconsin for having us here. I love cheese. You know, go Badgers. I sponsored S2907 with 74. You know, the whole, and the moderates say, well, Mr. Trump, what do you have said? Because I don't know what he just said.

7:59I'm going to build a wall. I'm going to build a wall 30 feet. You know, okay, you don't like that 50 feet. You can make it 50 feet. and you laugh at it, but it's damn straight and it's damn honest. You could call it straight talking. It might be stupid talking, but it's also straight talking. And we work for people who are trained to think before they speak, and that became a liability. So one aspect of prep that I don't know that you've talked about is the role McDonald's played. Yeah. I went a little overboard. I didn't do it as much. Well, actually in 2015, I think I was already pretty overweight.

8:34So, you know, he's 6 '3". God knows how many hundreds of pounds. I bought two and three-quarter inch lift shoes, which is the highest I could find, and then a platform. I couldn't do the hair. Last year, I was skinnier, and I went on a McDonald's. It was really just an excuse to have a McDonald's, but it became like super-sized me. I would, in the months leading up to it, just three, four nights a week, have two Big Macs, a shake, large fries. And I put on, I think, 34 pounds. Oh my God. It's like raging bull. And I went really heavy on the makeup this time. The hair, I talked to Lupe, the woman who's done my hair for 20 years.

9:21She said, if you get a wig, she said, we can't change your color hair. It'll be permanent. It'll be screwed up. If you get a wig, like a professional wig, I can color it, but even that won't be great. It's just clear that it would be too SNL-ish. But from the forehead down, it was pretty accurate. I dug up my Trump watch, my Trump cufflinks. I had given, after 2016, I put him in one of those bags. And he pulled the air out and everything flades down to this. I had given that to Ron Klain to use in 2020 if they wanted. And then I got it back from Ron. And everything, you know, still fit. Why do you think they didn't call on you to do debate prep in 2020?

10:02It's because they knew he would knock it out of the park. I think COVID and Bob Bauer played, I believe, who had known him forever, was his lawyer. Look, it's an incredibly intimate, it's not the right word, but it's incredibly intimate. You're seeing people at their worst. You're hearing them at their most honest to staff and to each other. I thought it was a real credit to Vice President Harris that she was up for it. Although when she brought me in, it was when she was VP candidate. So I was supposed to be Vance. Oh, I didn't realize that. So you had been brought in to play Vance with Kamala, and then you just transitioned seamlessly into playing Trump.

10:49Did you ever do any Vance prep or did you ever came to it? Yeah, I spent about two weeks, watched his debates, read up on him. I spent two hours of my life watching Bill Billy Elegy, which is just... But it's weird because there are big names in it, like Amy Adams and Glenn Close. Apparently, they all thought it was like a vehicle to the Oscars. I was halfway writing a memo about my first impressions when Rohini... I can never get her last name right. Rohini IM me that Biden had just dropped. I was like, okay, I'm done with that memo. So I want to understand the difference between 2016 and 2024.

11:27Obviously, Kamala Harris is not Hillary Clinton, and Trump in 2024 is not the same as Trump in 2016. I want to talk about both. What's the difference between preparing Hillary Clinton for a debate and preparing Kamala Harris for a debate? You know, as it turns out, much less than I would have thought. They both took it really seriously. They both put in the time and the hours. They both took the criticism well. I mean, it is an uncomfortably annoying situation to have people that you pay telling you that everything you just said and everything, the way you just said it is terrible and supposed to keep smiling about it.

12:03It's a time suck. And it's not like they take you off the road. You still have to go do fundraisers. You still have to go do rallies. You still do interviews. So I think they were pretty serious. And they were both serious in that. I mean, Hillary, Trump had never debated one on one. So there was a lot of sort of guessing about what that would entail. Hillary never took him for granted. She saw the power of her message from the first day. The very first day, we did like a 15-minute batting practice about the economy. And she did, you know, my budget has been scored by the CBO, and it's going to save$1.9 trillion.

12:42And then I went, and I was like, well, you know, I mean, Lawrence Kudlow. I mean, everyone knows Larry Kudlow. Larry Kudlow says, I got the best budget in the world. And then on immigration, it would be, you know, I got Sheriff Joe. I mean, if you've got Sheriff Joe, you've got the best. And she, you know, we stopped and she sat down and she said, it's so smart. No, no one knows who Larry Kudlow is, but he's telling them, he's naming someone. And I think that's just a very hard retooling you have to do when you're a U.S. senator, a governor, whatever it is, when you are talking Turkey, to suddenly play that game.

13:22It is a very challenging, but neither of them thought it was easy. But he's also the most predictable human being on God's green earth. So you can easily plot it out. So one example is people will say, how long before Trump loses his shit? and I'll say, when do you want him to lose his shit? You're a participant. You're not just a spectator. President Biden made him lose his shit in minute 80 about the golf, the inane golf exchange, about their golf scores. Now, Biden could have done that at minute 10 and gotten the same response. And I'm not saying that was a smart exchange, but the point is that you're not watching him.

14:11You can, he's an amoeba. He's just a single cell entity that is looking for food, for nourishment, and you can easily reroute him. So in 107 days, Kamala talks about the moment right before the debate where you let your guard down as Trump and kind of, it's a pep talk basically because you've been prepping so much. Everybody feels like one more session won't get you much because everybody understood going into the debate that the mentality really matters, that it matters that you're in a good headspace. And then we learn from that book that moments before the debate, Joe Biden calls ostensibly to wish her good luck, but then ends up distracting her with talk about people in Philadelphia, hearing she's bad-mouthing him and kind of distracting her.

15:01Did you know that call happened? And what was your reaction? I did not know it at the time. I think I knew it sometime in the weeks after. Um, obviously it was poorly, poorly timed. Um, but she did great. So I don't think it knocked her off of her game. Um, I'd like to think that my pep talk and really the whole session, you know, the Karen Dunn ran was exactly what was needed. You know, it was batting practice. It wasn't, we weren't throwing pitches at her head. Um, at that point it is what it is. And it's just, it's just hard debating him. I mean, when I sparred, when I did with Hillary, I think maybe 11 times for 90 minutes and probably, you know, six or seven times with Kamala.

15:45I would walk away thinking, I just beat them like a drum. And I don't think Hillary would debate that. There were once or twice, I think, net net, Kamala got the better of me because she was, she knew exactly how to needle, you know, thread the needle. But to their credit, if you remember, they challenged Trump to more debates before the debate was even started. So you're part of these two sets of prep sessions and these two campaigns. It's obviously an important part of your life and like sort of a milestone in your life. I think largely we view those debates as having been ones in which both Hillary and Kamala kind of did what they needed to do.

16:32They won those debates. They came in and they kind of held their own and came away stronger. and yet we lost both fucking elections. And Trump didn't prepare nearly as hard as either of our candidates did. Like what, it's so discouraging. Like, what do you take away from that? You'll never hear anyone again say, do debates matter? Because clearly a bad debate does matter. And people who have had bad moments and debates have lost. People who've had bad moments have won. Not really. I think Trump got beat at least two out of three times against Hillary. One of them was just ugly. I'd call it TKO.

17:16Kamala beat him like a drum. I went back and I watched both Biden debates from 2020. Trump was just angry. And he was really debating COVID at the time more than anything. COVID is the only fact checker that has ever been successful with him. He couldn't tell us something that wasn't true. COVID was too obvious. It was like telling us it's February. Well, I think maybe then right now, though, he's having... And inflation is... Inflation is now, he can't fact check people's experience. People's experience can finally fact check him. You're 100 % right. And I think it's the only two times he has been fact checked by some external...

18:00it's not that people fact check him. It's not Glenn, you know, Kessler. It's not Nate Cohn. It's not anyone on CNN. It's just reality. You can't tell people any more than Biden could. Yeah. Hopefully it'll catch up to him. Last question. Like what lessons are there for us as we're trying to figure out how to kind of outflank him, gain attention, get him on his heels, like whether you're in, yeah. You know, I hate to be, I think Donald Trump is doing what Donald Trump does best, just what he did in 2017 to 2019, which is sabotage himself. And that doesn't argue for us to just sit on our hands and hope that that happens again.

18:42But we do, in some sense, have to get out of his way. You know, if you're the bit about if your enemy is in a hole, stop digging. And there's that. There's, I think there's also, I mean, I guess what I'm answering is more like psyche management than anything else. He's not succeeding in the way that he is Democrats fear. He, obviously he has deported people. He, and I'm not belittling that, but the courts have caught up with him on a lot of things. He has not been able to fire people as much as he could have. And look, you and I have worked in the government, you know you can cut 40 % right there.

19:26Nothing he's doing is as effective as how it seems, because how it seems is him saying that things are great. You know, Sleepy Joe couldn't deport anyone. We're deporting more than anyone. It's just not true. The government, you know, the economy is A+++++. I mean, he could add as many plus signs as he wants, that's just not the case. I think there's no magic bullet with him. I do think the handling of the budget, giving in to him twice was probably not the best idea because he would have been blamed for it. I mean, I don't think that that's such a great, hard thing to say. And frankly, Democrats, you just listen to him less because he's just so, he raises your blood pressure.

20:18He's so antagonistic, adversarial, belligerent, bluster. If you want to know what he says, read the transcript or read an article about it. But if you watch him, you're just going to get upset. I think not take him too seriously. He's going to start with the 2028 stuff, hardcore. Now he does it to needle Democrats and they make the hats and all that. He's going to do it because he's going to be lame ducked. And he's seeing it with the Epstein stuff. He's seeing it in little ways. Obviously, it's not as terrible as Bill, but there are fissures. And I think it's important that Dems not lose sight of what he's getting killed on.

21:06The ways he's weak. He's going to do bluster, but he's weaker than he seems. He's vulnerable. I would not want to be a Republican running for Congress this year. And as long as we don't become, I mean, as long as we avoid being the greater of two evils, which apparently is what we were in 2024, we can do really well. Philippe Reines, so good to see you. Good to talk to you. You too. Thank you all for listening. If you want to hear the full episode with Philippe and get a lot more great content, ad-free shows, and more, please sign up for Friends of the Pod at crooket.com slash friends. Support Crooket Media.

21:44Become part of the community. We'd really appreciate it. and we'll be back with new episodes of Pond Save America next week.