The Daily - A Trump Dissenter Fights for His Political Life

Episode Date: May 19, 2026

In Kentucky today, amid record-low approval ratings, President Trump is asking Republican primary voters to reject Representative Thomas Massie, who has broken with Mr. Trump on a handful of votes. Instead, he wants them to elect his handpicked challenger. Robert Draper, who covers domestic politics for The Times, and “The Daily” producer Caitlin O’Keefe, travel to Kentucky to cover what has become the most expensive House primary in American history. Guest: Robert Draper, a Washington, D.C.-based journalist for The New York Times. Caitlin O’Keefe, an audio producer on “The Daily.” Background reading:  In Kentucky, fidelity to Mr. Trump is once again on the ballot. Photo: Michael Swensen for The New York Times For more information on today’s episode, visit nytimes.com/thedaily. Transcripts of each episode will be made available by the next workday.  Subscribe today at nytimes.com/podcasts or on Apple Podcasts and Spotify. You can also subscribe via your favorite podcast app here https://www.nytimes.com/activate-access/audio?source=podcatcher. For more podcasts and narrated articles, download The New York Times app at nytimes.com/app. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

From New York Times, I'm Michael O'Bowro. This is the Daily. You know what the name is? He is the worst person. His name is... What the hell? How did he ever end up in Kentucky? In Kentucky on Tuesday, amid his own record low approval ratings,

President Trump is asking Republican primary voters to reject a Republican congressman that they've elected seven times before. His name is Thomas Massey. Representative Thomas Massey. Massey's a complete and total disaster as a congressman and frankly as a human being. A fiercely proud conservative who is broken with Trump on just a handful of votes. We got to get rid of this loser.

This guy is bad. He's disloyal to the Republican Party. He's disloyal to the people of Kentucky. And most importantly, he is disloyal to the United States. of America. And he's got to be voted out of office as soon as possible. Instead, Trump wants

Kentucky Republicans to elect his hand-picked challenger, Ed Galrine, in what has become the most expensive House primary in American history. On the other hand, Ed Galron has my complete

and total endorsement. He's a true American hero, and he's a great patriot. Today, Times political correspondent Robert Draper and daily producer Caitlin O'Keefe traveled to Kentucky to find out whether a popular congressman can still dissent from an increasingly unpopular president. It's Tuesday, May 19th. Robert, welcome back to The Daily. Thanks for having me back. Anytime.

We have established. quite clearly on the show that President Trump has decided to use these midterm primary elections to try to take out his rivals within the Republican Party and impose as much discipline on the party as humanly possible. And so far, he's largely succeeded in that goal, taking out Republicans who fought him in Indiana and just a few days ago in Louisiana. And there's one last revenge race that remains,

and in your capacity as a chronicler of Republican Party and the fights within it, you decided that that race was the most important or at least the most interesting, which is why I'm talking to you from the place where that race is about to occur, Kentucky. Why did you decide that that primary was so important? Largely because Thomas Massey, the seven-term incumbent of Kentucky's fourth congressional district, has been more defiant pretty much than all. all the other Republicans put together. Repeatedly, Massey has defied Trump's wishes and has seemed cheerfully uncaring about what Trump wants him to do.

Right. There's nothing nuanced or hedging about his brand of, I'm doing my own thing here. Not in the least, no. And as a result of this, Trump has endorsed an opponent against him and is encouraging big Republican donors to back. that opponent. And tell us more about that opponent. Sure. The man that Trump has handpicked to oppose Thomas Massey is Ed Galrine, a dairy farmer, Navy Seal, and Trump stalwart, who has pledged to stand alongside Trump and help get his agenda pass. This is a familiar landscape for Massey. He's been through this before. In 2018, Trump, Trump, wanted Massey taken down, and it didn't bear any fruit. But this time, things are a great deal closer,

where Massey has comfortably won his primaries, sometimes with 81% of the vote. This time around, the polls suggest that the two candidates are dead even. And what's so interesting to me about this primary is that if ever there was a moment where somebody might defy political gravity and survive this routine onslaught from Trump when he thinks you've dissented too much, it might be massy in this moment

because of the economy we're in, with the inflation we have, and the unpopularity of the war that the president started. Perhaps if ever there was a moment for someone to stand up to Trump and actually survive their repercussions, it might be this moment. If, in fact, Gow Rine does win,

then this will suggest, among other things, that Trump's stranglehold over the Republican Party remains pretty much absolute. If, on the other hand, Massey prevails, lives to fight another day, that it may well suggest that at a time when Trump has exerted so much in an effort to take down a candidate but has failed to do so, that perhaps Trump's grip is not what it once was and may in turn emboldened not just Massey, but others like him to challenge a president whose unfavorables are on the rise. Well, Robert, remind us how Representative Massey came to be so defiant when it comes to Trump and why the president finds him to be so intolerable.

I think that it's in keeping with the brand that Massey has held up from the outset of his political career as this individualist, a confirmed eccentric, a kind of fiscal absolutist, a person who is for individual rights, that he would hold the line on things like no foreign aid, and that includes no carve-out exemption for Israel. Which almost all the rest of Republicans would find a carve-out for. Yeah, that's exactly right. And so Massey has been viewed really as a sort of darling within and certain elements of the Republican Party for being a purist, for basically saying, what I say, no increase in spending. I mean no increase in spending for anybody, including our military,

including our allies in the Middle East, such as Israel. He's opposed Trump's intervention in both Venezuela and Iran, saying they betray the idea of America first. And so he's gotten by on that for some time, and he doesn't mind being a lone wolf, you know, tends to sit by himself in the House chamber, you know, is sort of this off-the-grid cattle farmer who drinks raw milk. And so there is a kind of Paul Bunyan aspect to him.

Right. And of all the ways that Massey, the Maverick, the raw milk drinker, decided to go against the president, I think it's safe to say that the one he's going to be best known for and the one that is probably the most personally upsetting to President Trump is the way he decided to fight the president on Jeffrey Epstein. That's right. And this has been, I think, particularly vexing for Trump because he was never wholeheartedly for the release of the Epstein files. But his electoral base certainly was. Right. And Massey took those desires literally and became the champion of releasing the files. And at a time when Speaker Mike Johnson was being very, very deferential to Trump, if Trump doesn't want them released, that's fine. We'll recess the Congress rather than allow for a vote on

the subject. Massey remained insistent, began to work with a coalition that included the Democrat Roe-Connor, as well as a handful of other Republicans that all happened to be women, and convened hearings, held press conferences with some of the women who were survivors of Epstein, and really became the public face of it. Massey's determination was so great that Trump ultimately had to read the tea leaves and throw his own reluctant support behind the legislation, the Epstein Files Transparency Act, that in turn forced the Department of Justice to release those files. That was Massey and Rokane's legislation. Trump was against it. Then he was for it. But that Trump essentially had to declare defeat was a moment that he clearly

did not forget nor forgive Massey for. So you go to Kentucky to try to figure out what that version of being a maverick within Donald Trump's Republican Party looks like to Republican primary voters who are being told by the president to turn out Congressman Massey. That's right. And I did so because it's really difficult to obtain ground truth in any congressional primary from behind one's desk in Washington, D.C. but particularly it's a complicated endeavor here because this is Trump country after all. These are people who really, really love the president. And the idea of having a maverick congressman who they also like a great deal, but who is making the president from time to time look bad, is not generally speaking what voters have in mind. And it's the voters who now are faced with a choice. Right.

Their party leader has said, I want you to vote against Massey. I want you to vote for Ed Galrine. And now the question is, how important is that dictate from a president they so admire? So as the press is getting set up, this is a treat for all of us here in Boone County to have. So about a week before, the primary, Caitlin O'Keefe and I went to a Massey event in Boone County in the town of Burlington. This is the northern part of the district. We welcome Mr. Massey. It was an extremely well-attended event in the courthouse, standing room only.

Take questions. We have a microphone set up here. How much time do you make? At least 150 or so folks there. I want to start out by saying, tell you what I have got done in the last six months ago. And Massey began it with a presentation of a presentation of a, sort of his affirmative version of why a person should vote for him. First of all, I got a bill passed that has caused Prince Andrew to no longer be a prince.

The British ambassadors no longer the ambassador to the United States. And the CEO of the World Economic Forum, that guy had to resign because of the Epstein Files' transparency. He very quickly moved into his advocacy of the release of the Epstein files. and he emphasized that while he is a tried and true Republican who has voted with the Republicans 91% of the time, that those areas in which he has distanced himself or opposed Republican legislative matters, he makes no apologies for. If you're covering up for pedophiles, if you're trying to spy on Americans without a warrant, if you are bankrupting this country, then I am not voting for that.

And so there are a few times I've had to stand up, and that's why I'm in a race here where it's the most expensive race in a Republican primary in a country. It's a most expensive race in history in Kentucky for congressional race. Massey made a point also of talking about his opponent at Gow Rhine. I respect that my opponent as a military service, but I've seen some congressmen get this wrong when they get elected. They get to Washington, D.C., and they ask who do our report to? Do our report to the speaker? Do our report to the president now? He said that Gal Ryan is essentially a rubber stamp for President Trump.

And if that's what people want, an unflagging supporter who will do whatever Trump wants, then fine. But that's not who Massey ever was or ever will be. Well, when you're in the legislative branch, you don't report to the executive branch. I report to 750,000 of you. I'm a direct report to you here in Kentucky. You are my bosses. And he spoke probably for about 15 minutes or so. And then he immediately opened it up to the audience.

You're not just supported here in Kentucky. You are supported in the United States. And what kind of a reception does Massey get there? Well, many of the comments and questions came from people who are really adoring of Massey. You know, these were people who were really applauding his principles and are very much in lockstep and appreciative of his independence. But people complain that we send politicians to Washington and they're not principled. You stand for your principles and that's gold to me. Then came a few audience members who were a little more skeptical.

Like I was an amazing. Elizabeth Smith, Union can die. One of them was a woman named Elizabeth Smith. I've got to say for the first time, in this election season, I have been on the fence. Who said quite plainly, I'm not sure who to vote for. I support the president more than any other time ever in my life. And I truly believe that President Trump is really working tirelessly, tireless, every day for the New York. She had supported Massey in the past, but really was an unswerving devotee of President Trump. And people have been saying all these awful things that, oh, you don't support Trump and you don't this.

Please give me a reason to vote for you this time. Okay. And so Elizabeth Smith basically asked Massey, make the case for why I should vote for you when Trump wants me to vote the other way. she's basically saying, help me reconcile a dynamic of me liking you and me liking Trump. That's right. First of all, I'm not running against Donald Trump. Massey began his reply by reminding Ms. Smith that President Trump is not on the ballot. I truly do have respect for his effort and the job he's trying to do.

But if I win this race, I guarantee you he will come right back around. And when he defies the president, it isn't for defiance's sake, but instead to uphold the kind of America first principles that Trump himself ran on. But towards the very end of the Q&A session, another gentleman stood up. Who represented an altogether different point of view from the ones we'd been hearing. As I see, the big picture is that of all things going on the nation, Iran, the economy, politics, to DEI, woke, is everything. What person in the whole United States, maybe the world that understands everything,

has input to everything, is Donald Trump. He gets more information, more meetings, more everything, and knows more about all of this than probably Jamie Vance for everybody in Congress anywhere. He does. The man's basic point was the president knows more than you do, so why aren't you deferring to this man's obvious superiority in the knowledge and intelligence that he has.

Things like that, by four or five bills that you voted no on that were really important to me, representing me that you voted no on those, and I was really furious. I thought, you've got to be kidding. He said that, look, you turned on Trump. Trump is my guy. I voted for you. You run seven times, right? First six times I voted for you because I wanted to.

Seven times because you didn't have anybody primary you. This time you got somebody running against you. He hasn't done anything. I really don't know a whole lot about the guy, but Trump has endorsed him, and that means to me that he will help Trump pass the things that I want done, okay? That you aren't doing. This exchange lasted for a full 14 minutes.

Wow. It's amazing. I mean, it was really long, and at times kind of boring. Certain people in the audience got up and left, but Massey stood there very patiently, letting the guy have his say, and occasionally interrupting him not, with his own statements, but with questions posed kind of socratically.

You're aware, aren't you, that I'm the one who got the Epstein files released and that Trump considered this a borderline act of treason? What do you think he learned about the Epstein files that caused him to do a 180 that makes him smarter than the people in this room that they should have been hit? I agree with pursuing the Epstein files. I want to release two. But to me, he said it was a hostile act for me to do that. I don't know.

But to me, he knows a big picture. There might be things that you don't understand why he said that. That he's not even revealing to us. Mark said that he had no problem with the release of the files, but seemed to be suggesting that perhaps the president had good reason for resisting the release of them. There were over a thousand girls that got molested, raped, drawn into sex trafficking, recruited, at 15 years old, recruited other girls to get raped so that they wouldn't be raped.

They never, you won't find. I have no problem with what you do is actually false. I really don't think about. I went against Trump on. The one thing he cared about the most. What he was doing, in essence, was trying to reconcile his basic view that Massey was in the right with his larger faith in Trump and reconcile in Trump we trust. with America First Principles.

I believe if he did, there was a reason that he did that he could not tell you or tell the public. I don't give anybody that kind of trust. And by the end of it, I enjoyed this one with you. Thank you. Massey shook the guy's hand and said that he enjoyed it. I wonder, Robert, what you took from this exchange and really from this entire town hall by the time it was over.

Yeah, Michael, what became clear to me is that for as popular as Thomas Massey has been here in the past and really still is with many people, the split with the president is clearly registering with voters. Now, whether that's forcing them to reconsider their feelings about President Trump or deciding they aren't going to vote for Massey, they do understand the stakes of this race, which is you are either with Trump or you are against him, and there is no room for independence. What I later learned was that the guy running against Massey, the one who's got Trump's support, he understands that. And in fact, he's bet his entire campaign on it. We'll be right back. So, Robert, you end up spending time with Massey's rival in this race at Galrin. Tell us about that time. Yes.

Caitlin and I, a couple of days after the Massey event, attended a Galrine event. All right. So you guys can come in and start to do that. And it was kind of an odd event. I had to say it wasn't attended by voters, but instead took place in a manufacturing plant. Its stated purpose was to have the U.S. Chamber of Commerce announce its official endorsement of Galrine in the presence of a handful of members of the press. Please welcome at Galride. So the U.S. Chamber guy gave a very quick speech. Well, thank you for that. Can you all hear me in back, back here?

Can you hear me okay? I want to thank you for those kind of remarks. Gowryne then gave his own 10 or 15-minute talk. And how is he making his case about this candidate to CFS? I was 26 years old before I left Kentucky to go off to the Navy Seals as an officer. I want you to hold that thought. I grew up on the largest dairy farmer in the state of Kentucky. Anybody out there know anything about dairy farmer?

The first thing that Gowryne did was introduce himself, by saying that he's not a politician, that he is from a multi-generational farming family, that he won a multitude of bronze stars serving his country as a Navy SEAL. And then finally, more recently, was pressed into service again by President Trump. I'm proud to stand with President Trump, the Republican Party, his American First and Kentucky Always agenda. I added that, and the president said he liked that. When I said that, I told you, I said, America First. Kentucky always, I like that.

He always said, President Trump cuts the taxes. And right away, it became clear that his support for Trump, and for that matter, Trump's support for him, is really the message that he's running on. I mean, he didn't talk about what committee assignments he would like to have. He didn't talk about America's place in the world. He didn't talk about specific spending bills or really any legislation at all. President Trump needed conservatives in Congress to deliver for the American people

and what they voted for, what? What he talked about with Trump. If I remember, nearly 78 million Americans voted for President Trump, 131 states, is that right, including the swing states, and 312 electoral votes? That is significant. That's a message. And then after that... But Thomas Massey stood in the way, not just against President Trump, but against the party in America.

He described how Massey was the person who was standing in the way of this agenda being passed. Kentucky deserves in America. He'll stand with President Trump, the Republican Party, and conservatives, not against him. And that the 4th District deserved someone who was more in keeping with the man that they had voted for, Donald Trump, and that he would be that man. So thank you all for coming here. God bless President Trump, the Republican Party. God bless Kentucky. God bless the United States of America.

And I'll take a few questions. Thank you all for coming. Thank you all for coming, Jeff. And after that, he took about four questions from members of the press. And in its guardrails heavy nature, it seemed to be the exact opposite of Massey's free forum, anything goes, encounter that we'd had a couple of days earlier. And what do you think explains that decision making? Well, it's that there's a paradoxical element of his campaign that while Trump desperately wants Massey to be crushed with overwhelming force, This campaign is kind of doing so with a very, very light footprint.

And I think also is very careful about saying anything that could possibly offend the president who has endorsed him, which was why when I had an opportunity during the Q&A, you know, I asked him, you did say a couple of minutes ago that you stand with President Trump. And Thomas Massey has said that that's tantamount to you being a yes man, a rubber service. Are you going to be Trump's rubber stamp? And I wonder if you could comment on that. If you see yourself as someone who would be unswervingly with the president or someone who would be independent. And what does he say? So first of all, I want to give you scene center.

I guess I should have got five bronze stars to demonstrate my personal courage and independence to act on my own. I guess I should have served three times a SEAL Team 6 instead of two. But they have rules about that and you don't do so much. There's no point of importance about that. I got to get thanks to other folks that did that. But it's a long way from a dairy farm in the Ohio River to seal Team 6, and I'm not talking geography. You know, beyond describing his resume, he was essentially conflating individual courage with political independence, which struck me as two different things.

The president knows who I am. He knows what I stand for. He knows exactly who he was talking to. I am no rubber stamp. We'll never have. and said that being a rubber stamp was never who he was, nor who he would ever be. No, sir, E. Bob, I'll put a bow on it with this. I represent these folks here. I'm their servant leader, and the president knows that. You can count on it. But I wanted to push on that idea just to learn a little more from the candidate as to really just what he'd like to be as a congressman.

So I paid him a call. Robert Draper. Hey, Robert, where are you at now? And what exactly did you ask him? What did he say? And were you able to fully resolve this question of whether he was capable of being anything other than a Trump teammate? Yeah, I started in our brief phone interview by asking him the most basic of questions. I'm just curious to know what House committees you'd like to serve on.

You're a man of varied interests, and you could go in a bunch of different directions. So what do you have in mind? What's on your wish list? What House committees would he like to serve on? Right. I'm going to go to Speaker Johnson and the president and JD. I'm going to say, where you need me, coach. Just like when I played ball at Franklin Simpson, when I played ball at Center College, when I played Paul at Murray, that is a team sport.

Governing is a team sport. Now, I've got my desires. I've got places I think I fit, but he knows what the whole ball team looks like. Does that make sense? Sure. And the answer that he gave me was whatever the coach says. Speaker Johnson and President Trump would be the ones to make that decision for. him and that he would happily abide by it.

I mean, to state the obvious, this is quite different than Thomas Massey's vision of Congress, where independence is essential and the prerogatives of the Congress are to do what individual members think is necessary regardless of the team they're on, regardless of what the president wants. That's right. Yeah. And I pressed him later on whether he would have done as Massey did on the release of the Epstein files.

And he basically said, well, I'm for transparency, but I'm for transparency in a way that doesn't cause any conflict with the president. And I asked him, would you be in favor of overthrowing the Cuban regime, for example? And he said, I'm in favor of liberating the Cubans. But in whatever way the president wants to achieve that, I'm fine. So in our brief conversation at no point was there any suggestion that he would assert himself as an individual. instead he would be an enabler of whatever the Trump administration had in mind. And look, to be fair, this is the calculation he's making, that if he's going to have a shot in this race, he's got to present himself as an alternative to Massey.

And right now, Massey's biggest vulnerability is that he's lost the support of the president in a state where the president is very popular. So Gal Ryan is running as the alternative to that. And Gowryne has an incredible financial war chest supporting him, and by supporting him what I really mean is attacking Massey. You had said earlier that this race remains quite close, and so it's tempting to ponder all the implications of Massey surviving this, all the implications of Massey losing this race.

But I wonder if at the end of the day, those implications aren't so far apart. If Massey loses, Trump will have clearly shown that there's no tolerance for opposing him, even when somebody like Massey is staking out positions that are really grounded in what Trump claims his political movement is all about. But even if Massey wins, the message to everyone else in the Republican Party is, do you really want to go through what I just went through in the name of independence from Trump? And the answer is probably no. So either way, I might argue, Trump achieves his goal of imposing a very high degree of ideological conformity, right? That's right. It's definitely the case. But it also comes with a certain risk, right? I mean, because we've just come out with this poll, the New York Times has showing how on the generic ballot Democrats are up by 10 or something.

So to basically, you know, wed yourself to Trump is really to be rolling the dice that this fidelity to the president is not going to prove damaging to the entire party. And so, yeah, I mean, Trump has basically sent this message, which I believe win or lose by Massey is still going to be present. But meanwhile, Republicans cannot be inattentive to this greater electoral message, the stormclads that are. gathering, suggesting that when it comes to general elections, it's a deeply problematic thing, siding with the president. Right. I mean, if the midterms were held today, according to the New York Times poll that came out on Monday, the one you just referenced, it's very clear that Republicans would almost certainly

lose the House based on all the factors you just described. They wouldn't lose Massey's seat. Whether it's Massey or Gowryne, it's going to be held by a Republican. But nationally, these polls suggest swing districts are going to swing Democratic. And what Trump is saying to every Republican in this very expensive Massey race is do not dare trying to break with me, even if I am steering this car off the midterm cliff. Well, if Trump understands nothing else, he understands leverage. And he has always shown a willingness to use that leverage.

And that leverage includes no small element of fear. It does send a formidable message that you don't want. to tangle with this guy. And we have not seen any president, I think, in modern history, perhaps in the history of American politics, who has had such command over his party, even in defiance of public opinion polls, that would suggest that people be a little bit wary of that fidelity to Trump.

Well, Robert, thank you very much. My pleasure, Michael. We'll be right back. Here's what else you need to know today. On Monday, a jury rejected Elon Musk's lawsuit, claiming that Open AI, the artificial intelligence company he co-founded, had violated its original mission by putting commercial interests over the good of humanity. Jurors did not rule on the merits of Musk's argument.

Instead, they found that Musk brought his lawsuit against OpenAI and its chief executive, Sam Alman, after the statute of limitations had expired. And the Trump administration has created an unusual $1.8 billion fund overseen by the president's allies to compensate those who claim they were politically targeted by the Justice Department under President Biden. Democratic officials called it a taxpayer-financed slush fund that would enrich Trump's supporters, and they predicted it would make payouts to, among others, those convicted of participating in the January 6th riots at the U.S. Capitol.

Today's episode was produced by Caitlin O'Keefe, Anna Foley, and Olivia Natt, with help from Chris Benderick. It was edited by Devin Taylor and Rachel Quester and contains music by Pat McCusker, Marion Lazzano, and Dan Powell. Our theme music is by Wonderly. This episode was engineered by Chris Wood. That's it for the daily. I'm Michael Bobara. See you tomorrow.