The Fall of Kimberly Guilfoyle

Yesterday, Kimberly Gilfoil resigned from her post as U.S. Ambassador to Greece, and it was because of a Wall Street Journal investigation. During Gilfoil's Ambassador ship, the Wall Street Journal looked into allegations that she was using her position for personal gain. After that investigation was published, the journal received information about a series of text messages. Can you just give us a sense of how many text messages landed on your desk? Probably more than a hundred? That's our colleague Dana Matioli. Also we received emails, and by the end of this, my colleagues and I had gone through hundreds, hundreds more than a year's worth of text messages between the person who sent us the text messages and the then Ambassador to Greece. In multiple texts, Gilfoil talks about a potential payment of $100,000 to an American Express account. Honey, please, I need you to get this done for me today with a prayer hand emoji. What was your initial reaction to getting this tranche of text messages? You know, the text messages got sent to myself and my three other colleagues, and they were really just eye-opening. They were very graphic text messages, and the first thing we said about doing was authenticating them, right? The text were between Gilfoil and a man named Eric Dieters. Ultimately, Dieters didn't make the payment, telling Gilfoil that it would cost him his marriage. Later, Dieters provided the messages to Dana, and Dana got to work verifying that the text were real. So what we did was, myself and my colleague Rebecca Ballhouse got on a Google Meet video phone call with Eric Dieters, and we had him pull up his cell phone to the text messages with Kimberly Gilfoil. In the meet, Dieters clicked on the contact card and showed the reporters that the phone number he had been texting was the same cell as the one they need to be Kimberly Gilfoils. And then he very slowly scrolled through every single text message with her for over a year, and we read them to match what was sent to us with what was actually on his phone and to see the context in between the things that he didn't send us, of course, right? We were able to see over a year's worth of text messages to help authenticate these messages for our publication, which obviously we have very high standards before we publish anything. Through a lawyer, Gilfoil disputed the authenticity of the messages in the reporting, but declined to provide specifics. Through these text messages, what Dana and her colleagues were able to see was that Eric Dieters and Kimberly Gilfoil had an arrangement where he would pay her money and Gilfoil would promise Dieter's access to some of the most powerful people in the Trump administration. They were sort of both using each other in some ways, and when you read the text messages back and forth, you could see how much these two people seemed to need each other. Welcome to the journal, our show about money, business, and power, I'm Imani Mawiz, it's Wednesday, October 14th. Coming up on the show, the Wall Street Journal investigation that led to Kimberly Gilfoil's resignation. Eric Dieters said his dealings with Kimberly Gilfoil began during the early days of COVID. Dieters had launched a MAGA event called Freedom Fest. It was this festival in Kentucky in response to COVID-19 medical mandates, and in order to really get a lot of attention for this festival, Dieters sought to find someone closely aligned with the MAGA movement that could appear as a speaker, and he found Kimberly Gilfoil during that period and started communicating with her. And she had a big enough megaphone that she would be a good ambassador for this festival. At the time, Gilfoil was engaged to Donald Trump, Jr. and was a rising MAGA icon herself. She was a former Fox News host, the kind of spokesperson that Dieters was looking for. For her three speaking appearances, Dieters paid Gilfoil a lot of money. He had given her $300,000 over the space of a few years to appear at his Freedom Fest festival. So now I want to get into a little bit more color about Eric Dieters. Can you tell us a little bit about his background? Yeah, so Dieters is a pretty colorful character. He's 63 years old, he was an attorney, and he had a family business with his father where they had some gas stations, but he was also a lawyer. He's also had other pursuits. Dieters co-owned a restaurant chain called Snappy Tomato Pizza. He also had unsuccessful bids for Congress and Governor of Kentucky. He was a morning radio host in Ohio, and he was very closely aligned with the Trump administration. He says he's Trump today, Trump tomorrow, Trump forever. As a lawyer, Dieters had a reputation as the courtroom bulldog in Ohio, and he got a lot of attention. He's someone who speaks very loudly and could be very impassioned when he speaks to you. And I think some of that's gotten him some attention from the court system. In 2020, he was banned from entering a courthouse in Ohio's Hamilton County, after threatening on social media to burn it down. The Kentucky Bar Association twice suspended him, citing aggressive litigation strategies, false statements in court proceedings, and filing frivolous claims. So this is someone with a, you know, a past of his own. Dieters told the journal he retired as a lawyer. Regarding his run-ins with the court system, he said, quote, "These rules that are written by big law to hurt people like me, screw them." After Freedom Fest, Gilfoil and Dieters began to spend more time together, and he started offering to pay Gilfoil for more than speaking engagements. As Dana discovered inside his text messages, Dieters came to Gilfoil with two big requests. One is this tax write-off that he took that was being investigated by the IRS. Dieters told the journal that he wanted Gilfoil's help to solve a personal tax issue and get the attention of the IRS chief. The other issue he wanted help with involved an extradition request. Dieters was advising victims of an Ohio surgeon who had fled the country after allegations of malpractice. So when you speak to Dieters, the thing he gets most impassioned about is the work he's doing for these victims of this doctor who fled to Pakistan. And he's working with hundreds of former patients of this doctor who are suing the doctor for alleged medical malpractice, negligence, and fraud. In a lawsuit filed against Dieters, the doctor's malpractice insurer, MedProgroup, accused Dieters of a, quote, "calculated scheme to extract payments from the insurer." Dieters denied the accusations in an interview, calling it, quote, "the most ridiculous BS lawsuit of all time." The tech show Dieters asking Gilfoil for help getting the Justice Department to launch an investigation into the doctor and bring him back to you as soil. He also talked about plans to publicize the case. He wanted to get his story of the victims onto Tucker Carlson, which is a conservative media figure. And he said if she did that, he would pay her $1 million. A million dollars for help landing an appearance on Tucker Carlson. At this point, Dana could see in the text that Gilfoil was reassuring Dieters that she was doing everything she could for him. She really is trying to help him. She's giving him status updates of all the people she's trying to help him with this tax issue, all the people she's reaching out to around Tucker Carlson to get him on there. In one text message, she even says, "No one is working as hard for you than I am and that I might as well be your personal public relations." She basically says that she's never worked so hard in her life for anything other than what she's trying to do for him. During the months that Dieters and Gilfoil were texting back and forth, Gilfoil's political career was about to reach another level. In December of 2024, President Trump nominated Gilfoil to serve as ambassador to Greece. You know, when any ambassador is confirmed, they take a close look at your financial situation, because if you're someone who's in serious debt, you could maybe be swayed by foreign actors to do certain things. That could make you a liability, so that is something that's very closely explored in all of these senate confirmation hearings. At the same time, Dieters was getting impatient, waiting for Gilfoil to deliver on his request. And as her confirmation hearing neared, Gilfoil was becoming increasingly concerned that her texts with Dieters were becoming a liability. He starts openly referencing this financial arrangement they have, including with people outside of her, so people like her producer for podcasts, and then she starts getting angry and worrying that he's leaving a damning paper trail that could really hurt her senate confirmation hearing for her role as ambassador. She writes to him, "It's unbelievable when we have a private arrangement with you that you would now CC a producer talking about money. She got very concerned about Dieters being inscriminate and putting anything about their financial arrangement in writing. This is something that really seemed to stress her out." At certain point, she says, "You're going to cost me my ambassadorship. She's very worried that he keeps referencing the payments to her, their financial arrangement." She says things like, "Erik, I really wish you would stop papering all these things. It's really dangerous and not helpful to you or me, while you could simply just call me on signal and signals an encrypted chat app where things disappear and things are not traceable, right? So she does not want anything writing, but he keeps putting stuff in writing. In another text, she says, "What a nightmare. You'll literally cost me my ambassadorship. Stop writing." The communication with Deeders doesn't stop there. Eventually, Gilfoyle would ask him for a payment to her Amix account, which would cost her her ambassadorhip. That's next. In August of 2020, Gilfoyle was one of the key speakers at the Republican National Convention, where she gave a memorable sign-off. "Leaders and fighters for freedom and liberty and the American dream. The best is yet to come." In the four years between the two Trump administrations, Gilfoyle tried to parlay her status as a mega celebrity into several businesses. There were haircare and fragrance products, a political consulting firm, and a med spa. What we learned is that a lot of the things that she tried to launch barely got off the ground and were later shuttered. So for instance, in 2022, she launched something called American Dream, which she described as an upscale vodka and champagne brand. And she was seeking $2 million at the time, according to the pitch deck, which is actually really interesting. It's not a normal Wall Street pitch deck or a San Francisco pitch deck. It has all of these glamorous shots of her in full length gowns. It's very flashy. The pitch deck projected that American dream vodka would reach $75 million in revenue within three years. Gilfoyle later dissolved the company. So that's one instance. She also tried to launch a perfume called Florida Maga, which really didn't get off the ground, right? So there are a bunch of things like that that just really was trial and error and most of them did not launch. Do you have any reporting on what President Trump thought about Gilfoyle's mega-inspired businesses? So we report that during this period between Trump's first and second terms, he grew frustrated with Gilfoyle because she was soliciting investments from Mar-a-Lago members for her companies. You know, at one point, he complained that Gilfoyle was supposed to be raising money for him, but instead was at his club fundraising for herself. Then in 2024, Gilfoyle's engagement with Donald Trump Jr. ended. According to financial disclosures after the split, she had more than a million dollars in liabilities, including a boat loan and a mortgage. For her hopes to become ambassador to Greece, that debt could be a problem. And as her confirmation hearing approached, Gilfoyle complained to friends that she was broke, according to people that we spoke with. Just days before her confirmation hearing in July 2025, Gilfoyle reached out to Deeders with a pressing request. Can you read us some of the text messages that she starts sending to Deeders at this time? So the same week of her confirmation hearing is the most splashy text I think we see. So in July 3rd, over-signal, she sends him a PDF to an American Express wiring instructions. And it says, "You could just send it here. It won't show up anywhere if you wire money to American Express. That's all that will show. Please." And that was a pretty telling text. Eric also told us she came up with a cover before the confirmation saying, "You know, let's create a story that you owe me money from a long time ago." And she asked him to put in a letter that he owes her $100,000. In another message, "Gilfoyle tells Deeders, I will be your trump rider die." There's another text where she says, "Honey, please, I need you to get this done for me today." And she had a prayer hands emoji and then it had the PDF with the bill payment instructions for American Express. And like I said, this was just a few days before her July 9th confirmation ring. How did Deeders respond to that request for $100,000? He considered it at first, but then he ultimately decided he couldn't do it because he felt like she wasn't really getting what he needed. And he also said it could have affected his marriage. Why did he say that this $100,000 was going to be a deal breaker this time? I think for him, he just felt like she was just using him to get more money. And that the $300,000 he had already paid hadn't gotten him any favors with the White House. And he was very skeptical about shelling out another $100,000 if it didn't seem like any of the promises she was making would actually happen. I think he wanted to have the action before he paid her. So he wrote to her, "I have paid you $300,000 over the years. As of this memo, I have not received one favor. I am not naive or a sucker I need results." Again, Gilfoyle asked Deeders to stop creating a paper trail and to call her on signal instead. In the fall of 2025, Gilfoyle's ambassador ship was confirmed she spent a year in Greece. Publicly, her priority was trying to persuade European countries to pay a premium for American gas. Around this time, the journal started looking into how Gilfoyle was misusing her position at the embassy for personal gain. And then last week, it all came to a head when Dana and the team published their investigation about her text with Deeders. The day before the story came out, the reporting team called Secretary of State Marco Rubio for comment. Rubio was on a flight to Athens. After he landed in Greece, a reporter asked if he was going to do anything in response to the journal's findings. "We don't conduct these things on a press conference on a tarmac in a foreign country because you wrote a story or somebody else wrote a story because some source gave it to you. So get that out of your head because that's never the way it's going to work with me." In the days after the Wall Street Journal's investigation came out, Gilfoyle contacted the White House and said the text messages between her and Deeders were AI generated. According to people familiar with the matter, officials didn't believe her claims. Yesterday, on her very first day as White House press secretary, Kittie Zachariah had an announcement. "We have asked Ambassador Gilfoyle to resign. She has been a wonderful asset to the team and we wish her well." According to people familiar with the matter, Trump didn't speak directly to Gilfoyle before making the decision. Later that day, Gilfoyle resigned via social media post. A lawyer for Gilfoyle said that she had been paid to speak at events before her nomination and was owed a balance for traveling and supporting those events. Why is this such a big deal? I think it's a big deal because you know, these ambassadors are sent overseas to represent US interests abroad, right? They're supposed to develop these relationships and promote US business and it's supposed to be this like virtuous cycle. And from what we were able to report about the ambassador's time and creases, there were other things happening that did not fall into the remand of an ambassador and we've had a number of politicians come out and say that they will be investigating this conduct. You know, over the years and multiple terms, we have kind of seen this narrative of interesting relationships with foreign business leaders take place with different officials within the Trump administration. What was the line that Kimberly Gilfoyle crossed? Why is this case getting so much attention? I think partly it's getting so much attention because of how blatant it was. You know, we have all of these text messages and emails showing exactly how the sausage is made. I think that part of why this is getting so much attention is because of really how solid the reporting is. That's all for today. Wednesday, October 14th. The journal is a co-production of Spotify and the Wall Street Journal. If you like our show, follow us on Spotify or wherever you get your podcasts. Wear out every weekday afternoon. Thanks for listening. See you tomorrow. [BLANK_AUDIO]