Guilfoyle is gone, a new press secretary makes an inauspicious debut, and how safe is the White House, really?

Christy Strawser (0:00)

The day's biggest stories, the people behind the headlines, the conversations you won't hear anywhere else. I'm Christy Strawser, you're listening to Audacy's On Deadline. So Kimberly Guilfoyle, former wife of California Governor Gavin Newsom, and then former girlfriend of Donald Trump Jr. is out. After reports surfaced that she attempted to basically shake down a Trump supporter to pay her $100,000 American express bill in exchange for access to the administration, Donald Trump's new press secretary. And don't worry, we'll get to that too.

The press secretary announced that Guilfoyle has been asked to step down from her role as ambassador to Greece. Here's Phil Mateer in the Bay Area.

Marty Griffith (0:38)

You've known Kimberly Guilfoyle for years. What is going on here?

SPEAKER_3 (0:42)

When did the wheels kind of come off the cart?

Phil Mateer (0:45)

The wheels have always been spinning fast with Kimberly. Yeah, I first met her when she was a Deputy District Attorney in San Francisco. She's San Francisco native, and she was co-counsel and co-prosecutor with the DA Terrence Hallinan on the infamous dog mauling trial in Presidio Heights, where a woman who was taking care of a dog for an inmate at Pelican Bay, the dog mauled one of the neighbors, and it made international news. It also paved the way for Kimberly to move on to Court TV and eventually at Fox as well. But while she was at the District Attorney's office, she started dating a guy by the name of Gavin Newsom, who was a supervisor at that time.

She also started to have a feud with a fellow Deputy District Attorney by the name of Kamala Harris, which lasted for some time too. The office just wasn't big enough for both of them. And so she eventually married Gavin Newsom. They got divorced. She moved to New York. Court TV made way to Fox TV, made way to her dating Donald Jr. Trump, getting engaged to Donald Jr. Trump, that not working out, and Donald Trump giving her the appointment as ambassador to Greece. Some say to get her out of town. Well, they might have gotten her out of town, but not out from under the microscope. The lights are shining hard on her, both for her request for $100,000 help in paying down her American Express card before she got appointed.

Greek ambassadorship and for being kind of close with certain Greek companies that she seemed to be showing deference with and lobbying around with them in Europe as well. So put it all together, you got the latest chapter in the ongoing soap opera with all those characters involved.

SPEAKER_3 (2:24)

Yeah, now the White House is reportedly asking her to leave. Did she have a bright future back then? I mean, did it hit a curve somewhere?

Phil Mateer (2:34)

Well, she had a bright future, yes. She's always been very, very colorful and very aggressive, very outspoken. I mean, she's given me a lot of fun to be around. She does not guard it.

It was when she left Fox News. She basically got turned out there in some of the behind-the-scenes plays. I think there was even a movie made about it.

That's when she started hanging out with the Trumps and things just started going sideways. She confused where she was with who she was and whatever. I mean, let's be honest about it. When it comes to asking for favors or taking money or setting up deals, the Trump family is just notorious for it. Being in the presidency has only accelerated it, whether it's Eric Trump, Donald Trump Jr., or Kershner, the son-in-law. I mean, they're front and center mixing business with politics. The difference is none of them hold a paycheck from the government, and Kimberly does, and that puts her under a different line of scrutiny. It's going to be interesting to see what goes from here because she certainly has been around a lot of things and seen and heard a lot of things in her time in the Trump White House, both when and in the four years between the two administrations. So, as one person told me, they're going to have to handle her with care because she's like nitroglycerin, she could go off, and if she starts talking, it could get really interesting, really fast for the Trump administration.

Christy Strawser (4:05)

As we mentioned, the White House trod out Caroline Levitt's replacement as press secretary, Katie Zachariah, and it wasn't exactly a stellar intro. She stumbled and stuttered and struggled to get through her own introduction. Zachariah has four children and has worked in comms before for the Trump administration. She says she's a lawyer, so when asked by a reporter when she passed the bar, she said it was when she was in China with her husband, and that managed to raise even more questions. Here's talk show host Mark Cox from St. Louis.