Bulwark Takes - BREAKING: JD Vance Privately Advised Hillary Clinton's Campaign in 2016 (w/ Chris Whipple)

Episode Date: September 16, 2026

Sam Stein is joined by Chris Whipple, who wrote for Vanity Fair about the remarkable political transformation of J.D. Vance, from a young Trump critic at Yale Law School to Trump’s vice president and a potential MAGA successor. They dig into Vance’s behind-the-scenes efforts in 2016 to help Hillary Clinton defeat Trump and examine what drove his dramatic reversal. Was Vance always destined for MAGA, or did something change along the way?Plus, Chris shares what Susie Wiles told him about Vance’s evolution and why she viewed his transformation differently from other Republican politicians.Read more: https://www.vanityfair.com/story/jd-vance-yale-lawThe day always ends well with Casper. Right now save up to 30% on mattresses and up to 35% on everything else when you go to https://Casper.com.

Hey, everyone. It's me, Sam Stein, managing editor at the Bullwark, and I am pleased to be joined by Chris Whipple, prolific author, chronicler of Washington, D.C. politics. You may know him from his great coverage of chiefs of staff at the White House. He had a great story about Susie Wiles, and he's got a new story that's out on Vanity Fair by J.D. Vance and his time at Yale. It's titled Godin'Vance at Yale. It's a playoff William Buckley, obviously. And Chris is now on Substack. Welcome to the club, buddy. It's great. You can get them at Chris Whipple on substack. Go follow him there. He's going to be posting a lot there. Chris, I was intrigued by the story, both as a native New Havener, because there's little breadcrumbs about Yale culture there that I recognize.

And I'll get to that in a little bit. But because of, you know, you get a lot of coverage of J.D. Vance, and you read a lot about J.D. Vance. But you don't always find out stuff new about J.D. Vance. And I thought you pinpointed a period of his life that, was formative as college in law school, in this case is for a lot of people, but also says a lot about the guy. So as you started talking to people who knew him at Yale Law, what did you discover that you didn't know? Well, thanks for having me, Sam. I mean, Susie Wiles was obviously a wild

ride for me at Vanity Fair, but the story of J.D. Vance is equally amazing, I think, and maybe the stakes are higher because he's the GOP nominee. But I went to Yale Law School where Vance began this, you know, incredible journey from Appalachian Hillbilly and Ex-Marine, just back from Iraq to vice president. And in the beginning, I got to tell you, nobody at Yale wanted to talk about Vance. I mean, he's he's radioactive politically from both the left and the right for reasons we can talk about. But I got my big break in the form of a rare interview with Amy Chois. She's better known as the Tiger Mother for the book. Because of the book, she wrote, the sensational book, which was a kind of tough love manual for raising superstar children back in the day. But she's a Yale law professor

and she became a close friend and mentor to young J.D. Vance. She really shaped him in some ways. She really helped to create him. There would have been, I think, no Hillbilly elegy without Amy Choir who kind of coaxed it out of him, maybe dragged it out of him. It's an amazing story that we can talk about. Yeah. It's interesting because he comes into Yale and we know that.

the back story not because of Hillbilellogy. But what the portrait you paint is of this guy who seems really aggrieved and angry. I think someone described him as a drama queen. He's constantly threatening to leave Yale law. He thinks it's all elites. He doesn't really understand. He doesn't quite fit in. Obviously, he finds Usha, and that matters deeply for everything, really. But he's an outsider at Yale law. And yet he ends up becoming kind of the sensation there. So how does that happen. Yeah, it's, it's pretty amazing. I mean, it begins on day one and contracts class, maybe the most boring class at Yale Law School, but everybody was there. How dare you, Chris? Because Amy Chois was running the class and she was known as someone who could give, who could

make a clerkship with the Supreme Court judge happen with with her good friend Brett Kavanaugh and others that she knew. So that day, sitting in the front of, row is this dark-haired Indian woman girl, attentively taking notes. And in the very back row is this disheveled, kind of beefy ex-marine who nobody thought would be a lawyer, much less vice president. Guess who? J.D. Vance. Well, they ended up in a small 16 student class. They did moot court together. And Amy Chua said that Ushua, said that Ush, Ushunds, was about 50 billion times better than Vance at that. She was the breakout star. She was the person, she was the Hillary Clinton, if you will, of that class. Hillary, by the way, was Yale Law class of 74.

And but they, they obviously, he was, he fell head over heels for her. But as you say, he was a guy who was known for being angry about the Iraq war. He would, he would, he was. He was, he was, would knock back beers with fellow veterans, some of whom were in his class, ran in New Haven bars, and he would say, and he would rail against the Iraq war. Which bar, by any chance? Rudy's. Yeah, Rudy's was one of them. Rudy's was one of them.

So, yeah, your New Haven native. I was an undergraduate. I was there before Vance. And they didn't go to the snooty places like Moray's. the private eating establishment. Yeah, I was an Annaliffy's guy. R.R.P. You know, I don't, you're not a, you're not a like psychologist,

but I do want you to play the role for a little bit. It strikes me that Vance throughout his, you know, biography, his chronology, whatever you want to call it, is just in constant search of some sort of paternal figure. And obviously he writes about that and his upbringing. But Amy Truah is obviously. plays that role for him. And then he gets beyond that and Peter Thiel plays that role for him. And then he gets beyond that. And Donald Trump plays that role for him. Can you speak to that sort of need for someone to

be his guidepost? Well, again, he was searching for something when he was at Yale law school. Well, that's something versus someone. Well, something and maybe someone. But the something, I think, was some kind of, he'd lost his, you know, he'd had off and on church going and his troubled youth, obviously, in Middletown and in Appalachia. He was an atheist when he was in Iraq, but he was searching for some kind of meaning, he says, when he was at Yale law. That's what you call the peace God and Vance at Yale, the play on the Buckley book, obviously. Buckley famously thought that Yale was hostile to both. conservative ideas and religious faith. Vance shared that feeling, except he Buckley attributed

that to a leftist faculty, and Vance thought it was deeper than that. But anyway, he was clearly in search of something. He may still be in search of something. As far as I can tell, Vance has no coherent, you know, post-Maga ideological worldview. It's all over the place. But he would certainly say that he was searching for meaning. And when Teal, when Peter Teal came and spoke at Yale, the light bulb went off over his head. I mean, he felt there was a real connection with this guy. He says Teal was a guy who was a man of faith. and the fact that Vance could make a hell of a lot of money didn't hurt.

Yeah, that's the other thing that comes through. This is a man, obviously, in Vance, who has railed against elite cultures wherever he's been. You know, he could go through his anger, righteous anger at the architects of the Iraq War. You can go through what you just talked about, his aversion to the elites of Yale. You can go to his attachment to the MAGA movement, which was built on this. idea that elites have screwed over the working class. And yet, he has been one of the great beneficiaries of elite culture, using it as a ladder throughout his career to advance himself. Donald Trump is an incredible elite. Peter Thiel is the co-founder of PayPal. He is an elite. Amy Chua is the most

elite law professor in the country. Is there not a contradiction here? Yeah. I mean, it would certainly it would certainly seem to be a kind of phony populism that he's espousing when you look at all the people who got him where he is. Now, you may recall that Susie Wiles famously said to me in that Vanity Fair piece back in December that whereas Marco Rubio, whereas his pivot from Never Trumper to MAGA acolyte was principled, that in J.D.'s case, it was, well, you know, he's running for the Senate. It was sort of political. So look, look, one astonishing thing for Susie Wiles to say out loud, even if she believed it, right? But there you go.

So, you know, there's certainly a school of thought shared by many that J.D. Vance is a craven opportunist. And as, you know, Stuart Stevens put it to me, he'd be a Trotskyite if he thought it would advance his cause. Yeah, but sure, I didn't think so. She says, I have a very different view of JD. I do not think he changed it all. I think he's exactly the same guy. Amy Chua is a fan. She's all in for JD.

They are close friends to this day when, you know, when the would-be assassin stormed the White House Correspondix dinner back in whenever that was. And J.D. Vance was hustled to a safe room. one of the first people he texted was Amy Chois, who guess what, was in the ballroom wondering, hey, when are you coming back? That's how close they are. She is all in. She believes that he has not changed and that if you're going to be, but she would probably tell you that as some of her other, as some other friends of JD told me who were at Yale law at the time,

you know, if you've got to be. If you're going to be a politician, you have to be ready to jump for opportunities when they come along. Yeah, it's a bit of like, you know, what do you expect? Politicians act political. Actually, that leads me to the newsie anecdote that you have here, one of many, which is just the role that he played in the 2016 election. So, Vance, just to back up as a critic of Trump, openly talking about Trump being an opioid for the matter. acids. He backchannels, according to Hillary Clinton's campaign. This stuff has not been reported before. Although he votes for Evan McMullen in that race, he is back channeling to the Clinton

campaign to offer advice. And you have people, a person who serves as an intermediary for the Clinton campaign, having Jady called Jake Sullivan Clinton's top advisor, urging her to focus more on that blue wall, all those blue wall states, which she famously did not. And then you have this. He called me again, this is according to the source. He said, quote, I hate Hillary, but I hate Trump more. Trump can't win. He can't win. Hillary is going to lose, but she doesn't have to. And then no one really denies that this actually happened. All you have those that might have actually been a source close to Sullivan says it was actually about the basket of deplorables comment that Hillary made that JD called to say, hey, clean it up. But JD's team doesn't really deny that he

was offering unsolicited or solicited advice to the Clinton campaign in 2016, which is remarkable. Well, yeah, it's kind of what Ben Bradley used to call a non-denial denial. Yeah, a long one. It's an incredible story. Again, when you consider that Vance was in no uncertain terms, pox on both their houses. 2016, he could not bring himself to vote for either Hillary Clinton or Donald Trump. But then he starts talking to this intermediary and says, This message is brought to you by Casper. So you know what becomes more important the busier life gets?

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else when you go to casper.com. One last time, that's C-A-S-P-E-R dot com and save up to 30% on the mattress you deserve. But then he starts talking to this intermediary and says to the Clinton campaign and says, as you quoted, yeah, I hate Hillary, but I hate Trump more. He can't win. She's going to lose, but she doesn't have to. That's what he says. And this person, this intermediary, told him, hey, look, you know, I could put you in touch with him. But Jake Sullivan's busy. You know, they're running a campaign.

But Vance was on a mission, according to this source, this intermediary. He kept, he was insistent. And so he was finally put in touch with Sullivan. He calls Sullivan. It was six weeks before the election. It was not long after Hillary had made that unforced error in a donor's meeting where she said that half of Trump's voters could be called it could be in a basket of deplorables. And Vance tells Sullivan, again, according to this source, who was in a position to know, Vance tells Sullivan she's got to fix this, deplorable thing. She's got to focus.

he was trying to help Hillary Clinton get elected. I mean, that's crazy. And Trump forgave him ultimately for the stretch. But Trump presumably does not know this story. Does not know about the back. Unless it's possible that he does, but I'd be surprised. I don't believe that Trump has any idea that J.D. Vance, his VP, once upon a time, was going through back channels to a lot.

elect Hillary Clinton. Well, let's see how the fallout is then, which does lead to sort of the premise of the back end of the piece, which is what is actually, what is Trump's actual opinion of JD? So there's a friend who you quote who says, I think JD generally likes Trump. He thinks he's really funny. I also think Trump genuinely likes JD. He said, I think he likes Usha a lot because Usha is withholding. She's not going to suck up to Trump. She won't do it. That's just me. But I've seen it. I think he finds her classy. She's very pretty, but she won't dye her and I think he just likes her. I would quibble with whether Trump likes people who don't suck up to him,

but putting that aside. But then later in the piece, you do say, well, you say he's impressed. Trump is supposedly impressed by how Vance has slimmed down. I guess the Sousa Diet worked and how he presented himself on a recent book tour. But mostly Trump's been making Vance's life miserable, right? And not only by anointing him the public appointment for unwelcome more, that would be Iran, behind closed doors, the president has needleed his VP, he said to have cracked to some of his inner circle,

you stuck me with this guy. I'm stuck with him. It's a modern version of the Humiliation LBJ used to heap on his number two, Hubert Humphrey. So what's your takeaway? What is the Trump impression of J.D. Vance at this juncture? Well, look, I think that the whole story of Trump and Vance is fascinating and complex. And it goes back to that first meeting they had.

You know, I wrote about the first time Trump met with Susie Wiles in 2015, and Trump was blown away by the fact that he was in the room with the great daughter of the great Pat Summerall. You know, this is the kind of thing that impresses him. I think that, as you well know, Trump loves it when people who have attacked him come to him. come to him crawling or on bended knee. Vance has certainly done that. And by all accounts, the people who know, Vance was charmed, just charmed out of his socks by Trump when they first met.

Trump said, you said a lot of nasty shit about me. And Vance said, let's talk about it. And by the end of it, he was convinced that everything he'd ever said about Trump was wrong. 95% of what the conventional media reports is false. He, to me, when I was in the White House with Vance, when people in the White House were still talking to me, he told me he told me that Trump was, he defended Trump's remarks at Charlottesville. He told me that, no, the media got that totally wrong. You know, I don't know what the media got wrong about Trump referring to very fine people on both sides who were marching with neo-Nazis with teaky torches chanting blood and soil. But Vance is saying that that's wrong.

Not true. He'd never said that. So it's wild. And I think that at the end of the day, Trump loves the fact that Vance recanted all that. We hear Trump saying that about Michael Cohen. You've recanted everything. All is forgiven, even when he hasn't. So I get the psychology there.

But I think it's, I think Vance, we can talk more about this, but I think Vance is in a really difficult, fraught position. Because as one person put it to me on background, at a certain point, he's going to start to get traction, Vance is. if he is indeed the frontrunner. He's going to start to run ads. He's going to start to have rallies. People will pay attention. Trump will not be able to stand that. Trump will not be able to share that spotlight. And come next year, he will destroy him. He will take him down. So that's a, reasonable argument, given what we know about Trump. That's a real possibility. And I, and I will add that Steve Bannon, whom I also interviewed for this, we'll get to Tucker Carlson later. But Steve Bannon told me that he thinks this relationship is only going to go south in a hurry.

Well, it does, I mean, if we're being real about it, is there a relationship with Trump in politics that has not eventually gone south? I mean, there's no amount of, you know, the loyalty is usually in one direction. and you can be one of the great suckups of the world. You can acquiesce as much as you possibly can. But eventually those relationships go south. And surely Vance is aware of that. Almost inevitably. Right.

If fans were put in a position, so Mike Pence is the obvious comparison, right? First VP. He is the ultimate loyalty guy, does whatever Trump wants, and then eventually gets to a place where he's like, I can't do that. and that's on January 6th. Right. Is Vance capable of that sort of independence, or is he too subsumed at this juncture?

Well, Vance, let's take Vance had his word. Vance has said, and I don't have the, I'm only paraphrasing, but Vance has said that he wouldn't have done what Vance did on January. What Pence did, yeah. He said it out loud. We don't have to guess. We don't have to really speculate about what would happen. Yeah, but is there a line you think?

think, is there a line you think that he would draw? I mean, you would think January 6 would be the line, but do you think Vance has a threat of independent thought still? Or is he just totally bought into the Trump project? I think he's all in. I think he has to be aware that he's in a really difficult position. I mean, he can't run away from Trump. And so he's carrying the baggage of affordability, inflation, a war-gone haywire. Every other problem that Trump has passed along to Vance, he's going to have to run with all of that, including his inability to solve this pointless war of choice.

So Vance has to carry all that baggage. And unlike a potential rival, for example, Rubio, Or even, who knows, Bobby Kennedy Jr. No, let's talk Tucker here because I think Tucker's the more interesting one. Because Tucker at least has said, hey, I don't like this war and he broke with Trump over the war. Vance can't do that. Yeah. No, exactly right.

So, you know, think of Hubert Humphrey in 1968, who at the very end of that campaign, October 30, finally created some distance between himself and LPJ on his conduct of the Vietnam War. it was too little too late. And it was almost impossible for him to break with LBJ. The same thing is true for Vance. He's got mission impossible in a way. All right. Last question for you. But there's a line here that's stuck out from me. But almost two years into Trump's second term, it's still the central question of advance. Does he stand for anything other than his own advancement? So you spend a lot of time talking to people who know him, who nurtured him. You spend a lot of time talking to people. inside the White House, you talk to Tucker, you talk to Steve Bannon. What did you come away with an answer on that? Well, it seems to me there are two schools of thought about J.D. Vance. One is we've already discussed, which is the notion that he's the cynical opportunist who will just blow with the wind.

But the other school of thought is that he is unlike Trump, who has no convictions or beliefs and is transactional about everything, that Trump, that Vance is actually a true believer in a post-Trump mega ideology, a worldview that is more authoritarian, and is in fact a kind of Catholic theocracy. And it goes back to this guy, Patrick Deneen at Notre Dame, that Vance, along with Peter Thiel,

Danine's been a huge influence on Vance. And Jacob Heilbrun is a guy I interviewed who lays this out pretty in an interesting way. That's a real worry about Vance is that he actually believes in this stuff and that he has the intellectual shock troops in place. I mean, a bunch of people who have followed him, some of them from that class at Yenai. Law School. So take your pick. Neither one sounds like a great option to me, but there are people who think that Vance is actually a true believer in something that is much more ideological than MAGA. Yeah, but it just strikes me that you can't go within 10 years from secretly advising Jake Sullivan on how to clean up the deplorable so that Trump won't win to now believing in this

stuff. Like something seems a little bit off-kilter. Well, yeah, look, it's also possible that both things could be true. Yeah, I guess so. Yeah. Look, I think it's, as I say, for me, it was, it was an amazing journey. I spent the last six months starting at Yale Law School, tracing his journey from there to where we are now. And I hope everybody will read the piece and also check out my new sub-stack. Yes, good plug. All right, Chris Whipple, who has written for Vanity Affair, God and Vance at Yale. You should check it out. It's a great piece. And as you

mentioned, he's on sub-stack now. You just got to follow him at Chris Whipple. So Chris, thanks so much, man. Really appreciate it. Great work. Sam, thank you. Always great to be with you. Take care.