What A Day - A Look At Trump And Epstein's History

Episode Date: July 22, 2025

Despite President Donald Trump's best efforts, his administration can't escape the conspiracies swirling around convicted sex offender Jeffrey Epstein — conspiracies Trump and his allies helped stoke before he returned to the White House.On Monday, House Speaker Mike Johnson said he would not permit a vote this summer on a non-binding resolution calling for the release of documents and records related to Epstein, who died by suicide in 2019 before his federal sex-trafficking trial. And on Friday, Trump sued The Wall Street Journal for billions of dollars over a story alleging he sent Epstein a lewd birthday card in the early 2000s, when the two were known to be friends. Trump has always denied any knowledge that the disgraced financier was abusing underage girls and young women, but there's no denying the two men frequently hung out together, often in the presence of young, attractive women.Matthew Goldstein, a New York Times business reporter who covers white collar crime, joins us to talk about the backstory of Trump and Epstein's friendship, and why the administration can't make this story go away.And in headlines: Some foreign travelers will have to pay a new $250 fee to enter the U.S. thanks to a provision in Trump's new Big Beautiful Law, a new Human Rights Watch report alleges 'dehumanizing' conditions across immigration detention centers in Florida, and Texas Republicans kicked off a special legislative session to potentially redraw the state's congressional map to help Trump in next year's midterm elections.Show Notes:Check out Michael's piece – nytimes.com/2025/07/19/us/politics/inside-trump-epstein-friendship.htmlCall Congress – 202-224-3121Subscribe to the What A Day Newsletter – https://tinyurl.com/3kk4nyz8What A Day – YouTube – https://www.youtube.com/@whatadaypodcastFollow us on Instagram – https://www.instagram.com/crookedmedia/For a transcript of this episode, please visit crooked.com/whataday

It's Tuesday, July 22nd. I'm Jane Coaston and this is What a Day, the show that is noting that according to CBS News, President Donald Trump's approval among 18-29 year olds has gone from plus 10 in February to minus 44 in July. That's a negative swing of 54 points. Apparently the youth are not as excited about masked ICE officers and tax cuts for billionaires as some may have thought. On today's show, some people visiting the U.S. will need to pay a fee to get in thanks to a provision in Trump's big, beautiful law. And Texas Republicans are trying to redraw the state's congressional map to help the

president in next year's midterm elections. But let's start with Jeffrey Epstein. President Donald Trump apparently does not want to talk about convicted sex offender Jeffrey Epstein. When the Wall Street Journal reported on an alleged birthday letter from Trump to Epstein that featured a nude doodle and a cryptic message last week, Trump sued the paper and its owner, Rupert Murdoch, and his media company, News Corp, on Friday for billions of dollars. The White House also removed a journal reporter from the press pool for Trump's upcoming trip to Scotland. And the President's allies in Congress are following suit.

Speaker Mike Johnson said Monday that he would not permit the House to vote on a non-binding resolution — a non-binding resolution, calling for the release of documents and records relating to Epstein, at least not before the August recess. Instead, Trump would seemingly rather talk about Rosie O'Donnell, or changing the name of NFL team the Washington Commanders, or a conspiracy theory involving former President Barack Obama and Russian interference in the 2016 election that the conservative magazine National Review called quote frivolous and quote thundering claptrap but not Jeffrey Epstein. In fact, if you have questions about Jeffrey Epstein,

Trump says you are a bad person. Here he is speaking on the subject last week. I don't understand why the Jeffrey Epstein case would be of interest to anybody. It's subject last week. I don't think something can be both sordid and boring. But anyway, all of this is odd. I mean, for the last three years or so, members of Trump's circle of influencers, including multiple future administration officials, were jazzed to talk about Jeffrey Epstein to pretty much anyone who would ask. So what changed?

How did Trump go from sounding like this in conversation with podcaster Lex Freeman in September discussing Epstein's clients and his private island, Little St. James, The list of clients that went to the island has not been made public. Yeah, it's very interesting, isn't it? Probably will be, by the way. So if you're able to, you'll be... Yeah, I'd certainly take a look at it. to posting on True Social that he doesn't want the support of anyone who bought the quote, Jeffrey Epstein hoax. As a former Democratic vice presidential candidate once said, that sure is weird. Also weird is why Trump even leaned into the Epstein conspiracies in the

first place, given their well documented friendship when the two shared social scenes in New York and Palm Beach, Florida in the 90s and early 2000s. That's where the whole birthday card allegation comes from. Trump has always denied any knowledge of Epstein's abuse of underage girls and young women. But there's no denying the two frequently hung out together, often in the presence of young, attractive women. Trump supporters were willing to overlook those ties for a long time, but that might be changing now.

So for more on the backstory of Trump's relationship with Jeffrey Epstein and why the administration's efforts to shove this story under the rug have failed, I spoke to Matthew Goldstein. He's a New York Times business reporter focusing on white-collar crime, and he's been reporting on the Epstein case. Matthew, welcome to What a Day. Hi, thanks for having me. So I guess let's start from the beginning. When did Trump and Epstein first meet and how did they become friends? Well, you know, it's still a little bit murky, but believed to be sometime in 1990, 1992 timeframe when they first met. Basically that relationship began like two guys who were sort of well-known in the New York and in the Palm Beach area of Florida where they both had places to be.

And they often would be at parties together, different events together. You know, it's sort of a relationship that sort of grew. I mean, I know the president has basically said they weren't particularly close friends. It's always hard to distinguish what is a friend and what isn't a friend, but it's clear that they were hanging out a lot together and went to events together. One of their clear shared interests

was their love of pretty young women. Now, Trump has maintained for years that he had no idea Epstein was abusing young women and underage girls. We have to note that Trump has never been accused of wrongdoing in connection with Epstein's cases, but what have these women said about Donald Trump? Yeah, I mean, one thing, let me just start off. Like, you know, when we talk about young women, a lot of the very underage women, the 14, 15, 16 year olds, that really was sort of Epstein's thing.

But that said, there were also a lot of women who were 17, 18, and 19 years old. No one has seen anything in terms of ultimately improper, but a few women have said, one is a woman, Stacey Williams, who actually came forward right before the election. And she has been around in some of the media talking about how Epstein brought her over

to meet Trump at Trump Tower. This goes back to 1993. And immediately Trump starts roping her. And she said, it was sort of like an octopus who was sort of all over her. And she came away sort of feeling this was sort of like a game between them. Like look who I got What do you think about her between Trump and Epstein you mean? Yeah, Trump and Epstein to basically see who can get the best the best woman basically other women

We've talked to or I've talked to over the years and said that they felt that They were being ogled by the president There's one other woman at an event, a Victoria's Secret event, who said that she felt that she was somewhat also groped by the president. But it was a lot of what it is, it seems to be sort of like this, like I said, this competition,

which is just sort of creepy and weird. And obviously, at that time, they were probably in their 40s. And most of the women they were going after were like basically 2021 at that time. Eventually, Trump and Epstein had a falling out over a real estate deal in Florida around 2004. What happened? Well, there's several different versions of their falling out. So the real estate deal was they both were vying for the same property in Florida. And apparently Trump went out and Epstein was pissed off and they had a fight and that

sort of ended to their relationship. Trump's argument is actually that the real estate issue really wasn't that important. What really happened was he was upset because he found out that Epstein had tried to approach the daughter of a Mar-a-Lago club member. When did he start telling that story? He started telling that story when he was asked about Epstein, like basically around 2008-2009. It's very well possible both versions are somewhat right. like basically around 2008, 2009. It's very well possible both versions are somewhat right, because one can clearly see that Epstein had made an approach to women at Mar-a-Lago, too. Trump has told that version to a bunch of other people.

He told it to Brad Edwards, who was one of the big lawyers to the victims in the Epstein cases. And when Edwards was doing work on litigation in 2009, he had reached out to Trump about Epstein and about the relationship. And that was like the basic standard line that Trump has said. And he has sort of generally stuck to that, that line since. Pretty soon after their falling out, Epstein was arrested for the first time. He eventually pleaded guilty to state charges of soliciting prostitution from a minor. Then in 2019, he's charged with federal crimes of sex trafficking and

conspiracy to traffic minors for sex. A few months later, Epstein hangs himself in prison ahead of his trial. But given Trump's long friendship with Epstein, and here's what's been wild to me. How has Trump been wild to me, how has Trump been able to avoid more scrutiny from his base really up until now, despite the fact that there are photos and images and video of Epstein and Trump together? Yeah, I mean, it's sort of hard to get into like the MAGA base mindset. In the president's defense, you can argue whether he knew or did not know what was going

on with Epstein, he cut it off before he was charged. So I think some give him credit for that. I think some look at it also, again, in a creepy kind of way. In the late 90s, it was a different kind of culture. Some things that were accepted then are not accepted now. But if you look at just generally allegations that have been about Trump throughout the years, they seem to have slid off him.

You know, I guess it's just that there's a very, of his base, I think they're just very forgiving. And I think unless they're, quite frankly, is something specific, maybe with an underage girl, I think that might be a game changer. But we just don't have that, obviously, and we don't know if that even exists. Trump's base has, at least for somewhat now, has turned some of their ire towards the Wall

Street Journal for the story alleging Trump sent Epstein a lewd birthday card with a doodle of a naked woman and mention of a, quote, secret. The New York Times has not independently verified the story and Trump flatly denies it and he's suing the journal for billions over it. But do you think that that's a good strategy? Because I would think if I want something to go away, I am not going to sue someone for billions of dollars where we're going to have to go to discovery, we're going to have to go to court to keep talking about it. It seems like that's not how you make something go away. Do you think that this is over for trump now? Yeah, I I it is sort of baffling Um, though as we've seen his strategy seems to be to sue the media when some things come out that he doesn't like

Um, you know, look I give the journal credit. It was a good scoop to get Um, you're right. We haven't confirmed it. We know there was a birthday book. We haven't confirmed what was actually in it. You know, to me, it doesn't really change the dynamic of what people have sort of thought. You know, they were friends. We know that. So to me, I almost think you could have said, okay, it was a birthday book. I signed it.

Big deal. I think maybe this is just part of his general strategy of trying to rally the base and distract from it. I know people have said it opens up the door to discovery, which it does, but that assumes that this case actually gets anywhere as close to trial. My guess is probably within a month or so, maybe they quietly dismiss this lawsuit and just let it die or something and move on or maybe they happily hope That doesn't survive a motion to dismiss

And goes away and then they can say at least we put up the good fight Trump has managed to keep his base behind him on some giant Scandals, which even seems like a weird way to refer to something like January 6th, but let's go with it. And, you know, his claims about the 2020 election being stolen from him have become just bog standard views among his base. There's even going back to the Access Hollywood tape, I could keep going. But why has this feels different? Why has this turned into one of the biggest controversies of his second term, at least among the cracks it's creating among his base, especially the most visible members of his base. Is it because he basically did it to himself?

Yeah, I mean, I think yes and no. I mean, and this is where I come in. I've been reporting what I call the money trail for the past six or seven years on this. And, you know, the Epstein story, on one hand, it's gross, it's disgusting, the sexual abuse of minors and even women, young women. But what makes it sort of stand out is the fact that, aside from just Trump, he had surrounded himself with all these powerful people in the world of finance, in academia, celebrities. In some ways, it sort of boggles the imagination why. I mean, Epstein wasn't, I mean, I've been told he was charismatic,

which I'll give him maybe he was. He didn't seem particularly skilled at anything. I mean, he claimed he was a tax expert, but there's no real sense he really was. He wasn't really a great money manager. He often lost money for some of his clients. So, you know, I think that's the idea that the what I think unsettles a lot of people. Why did all these wealthy people, particularly men, hang out with him for all these years and want to be around him? And I think the fact that no one has ever really come up with a really good explanation except for all the men saying, oh, we weren't aware of what was going on, which has sort

of been the standard Epstein line. So I think that sort of ends to why this keeps feeding upon itself and doesn't go away. Matthew, thank you so much for your time. Thanks for having me. That was my conversation with Matthew Goldstein, a New York Times reporter focusing on white-collar crime who has been reporting on the Epstein case. We'll get to more of the news in a moment, but if you like the show, make sure to subscribe, leave a five-star review on Apple Podcasts, watch us on YouTube, and share with your friends. More to come after some ads. [♪ Music playing.

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I may take my business elsewhere. That's CNBC's Monica Petrelli reporting on a little known provision in Trump's big, beautiful bill-turned-law that will require visitors to the United States to pay $250 to enter the country. The new visa integrity fee will charge anyone on a non-immigrant visa, like a student visa or temporary work visa, $250 on top of any other fees they would already pay. The cost cannot be waived but it might be reimbursed if you comply with visa restrictions. The administration

claims the integrity fee is designed to keep people from overstaying their visas. But this is still a concept of a plan. How or when the collections will start hasn't been announced. Or how to get reimbursed for it. Though the Congressional Budget Office says the fee could make the government around $29 billion, because it's counting on people either not knowing how to get reimbursed, or not wanting to go through the hassle. not knowing how to get reimbursed or not wanting to go through the hassle. A Human Rights Watch report out Monday alleges, quote, dehumanizing conditions across immigration

detention centers in Florida. The report includes countless horror stories from detainees, including claims of being forced to kneel with their hands cuffed behind their backs and eat from styrofoam plates, quote, like dogs. The write-up also attests that detainees have been denied medical care, which could have led to at least two deaths. The dispatch is a collaboration between Human Rights Watch, Americans for Immigrant Justice, and Sanctuary of the South, and is based on interviews conducted with current and former detainees. In a statement that was released with a report, a spokesperson from Human Rights Watch said, quote, These are not isolated incidents, but rather the result of a fundamentally broken detention system that is rife with serious abuses.

The authors of the report draw a connection between the Trump administration's increased immigration arrests and overcrowding in the facilities, which might get even worse, according to border czar Tom Homan at a press conference Monday. Every sanctuary city is unsafe. I'll say it again, sanctuary cities are sanctuaries for criminals. And I'm going to work very hard for Secretary Noem to keep President Trump's promise and his commitment several weeks ago that sanctuary cities are now our priority. We're going to flood the zone. So we can look forward to more of all of this.

The report recommends, quote, community-based alternatives to detention, as well as independent oversight and immediate steps to address abusive conditions. A federal judge in Massachusetts heard oral arguments Monday in Harvard University's lawsuit against the Trump administration over funding cuts that it says are illegal. Earlier this year, the government froze over $2 billion in grants and contracts, which jeopardized potentially life-saving scientific, medical, and technological research. The government's attorneys claimed the cuts

are punishment for the university failing to address Trump's executive order to combat anti-Semitism on campus, while lawyers for the university claim the cuts violate the First Amendment. U.S. District Judge Alison Burroughs didn't make a decision from the bench on Monday. She appeared to lean in favor of the university, though she asked both sides tough questions.

Burroughs said it didn't seem the government followed a protocol before making the cuts and that the administration made, quote, no documentation, no procedure, no process to suss out whether Harvard has taken enough steps to combat anti-Semitism. She also said the potential consequences for constitutional law in this case are, quote, staggering. After the hearing, Trump attacked Judge Burroughs, an Obama appointee on True Social, calling

her, quote, a total disaster, asking, quote, how did this Trump-hating judge get these cases? He, of course, concluded with his new catchphrase, thank you for your attention to this matter. At the time of our recording, Burroughs had not issued a decision, but is expected to do so very soon. Texas Republicans, at the urging of their MAGA overlord, President Trump, are poised to redraw the state's congressional maps this week. Former Democratic Representative Beto O'Rourke of Texas weighed in on the GOP's goals. Why are they doing this? Donald Trump's policies, whether it's the big beautiful bill that's going to take nearly two million Texans off of Medicaid or transfer nearly a trillion dollars of wealth to the

richest 1% at the expense of working families, his policies are deeply unpopular. He doesn't want to face accountability from the voters and he's worried about keeping his very slim majority in Congress. So he's trying to pick up five seats through this redistricting process in Texas. O'Rourke spoke to CNN's Jake Tapper on Sunday about the mid-decade redistricting push in the state.

The special session of the legislature started Monday. Texas Republican Governor Greg Abbott called it to address the recent floods and Trump's request to redraw the congressional maps, among other issues. Trump is desperately trying to avoid the traditional midterm letdown that most incumbent presidents endure and hold onto the House in the 2026 midterm elections. O'Rourke said, though, that the effort could backfire. This may end up biting Republicans in the ass. You have the possibility that they will disperse Republican voters

to make up these three or four or five new congressional districts and put those districts in play. He also said it's time for Democrats to match fire with fire, suggesting similar efforts in blue states. California Democratic Governor Gavin Newsom is exploring the possibility of redistricting in his state to help his party. And that's the news. Before we go, great news! What a Day has new merch!

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Check it out and subscribe at crookah.com slash subscribe. I'm Jane Coaston and at this rate we might finally get all of Trump's tax returns. What a Day is a production of Crooked Media. It's recorded and mixed by Desmond Taylor. Our associate producer is Emily Foer. Our producer is Michelle Alloy. Our video editor is Joseph Dutra. Our video producer is Johanna Case. We had production help today from Greg Walters, Matt Bird, Tyler Hill, and Laura Newcomb.

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