You remember the high heels, the sharp legal mind, and that "The Five" desk where things always seemed two seconds away from a shouting match. For seven years, Kimberly Guilfoyle was the glue—or the firecracker, depending on the day—of Fox News’ afternoon powerhouse. Then, in 2018, she was just... gone. No big farewell tour. No teary montage. Just a "parted ways" statement that left viewers scratching their heads.
Honestly, the story of Kimberly Guilfoyle from The Five isn't just about a cable news exit. It’s a wild trajectory that starts in a San Francisco courtroom, moves through a marriage to Gavin Newsom, and ends up in the inner circle of the Trump family.
But why do people still talk about her time on that specific show? Because she represented a specific era of Fox. She was the prosecutor. She was the one who wouldn't let a point go.
The Rise of the "Legally Blonde" Prosecutor
Before she was a household name, Kimberly was literally putting people behind bars. Most fans of "The Five" don't realize she was a heavy-hitter Assistant District Attorney in San Francisco and Los Angeles. She wasn't just some talking head; she was the lead on the 2002 "dog mauling" case that gripped the country.
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It’s kind of ironic.
The woman who spent years married to Gavin Newsom—the current Governor of California and a liberal titan—ended up becoming one of the most recognizable conservative voices in the country. They were once dubbed the "New Kennedys" in a Harper’s Bazaar spread. Life comes at you fast. By 2006, she’d moved to New York, joined Fox News, and started her climb.
When "The Five" launched in 2011, it was supposed to be a temporary replacement for Glenn Beck. Nobody thought it would last. But the chemistry between the original cast—Kimberly, Greg Gutfeld, Dana Perino, Eric Bolling, and Bob Beckel—was lightning in a bottle. Kimberly played the "tough but glamorous" role perfectly. She brought a prosecutor's edge to every segment, often holding her own against Bob Beckel’s old-school liberal grumbling.
Why Kimberly Guilfoyle from The Five Actually Left
The official story in July 2018 was that Kimberly was leaving to join the Trump campaign trail with Donald Trump Jr. At the time, they had just started dating, and the MAGA movement was hitting a fever pitch.
But look closer.
The exit was abrupt. Reports from outlets like The New Yorker and HuffPost later painted a much messier picture. Allegations of workplace misconduct and a toxic environment followed her departure. Specifically, there was a secret $4 million settlement paid out by Fox News to a former assistant. Kimberly has always denied these claims, her legal team calling them "patently false."
Regardless of which side you believe, the result was the same: a permanent break with the network that made her a star. She didn't look back. She traded the "The Five" desk for campaign stages, becoming famous for that booming 2020 RNC speech where she shouted, "The best is yet to come!"
Where is she in 2026?
A lot has changed since those afternoon broadcasts in Midtown Manhattan. If you’ve been following the news lately, you know her political loyalty paid off in a big way. In late 2024, Donald Trump nominated her to be the U.S. Ambassador to Greece.
She was confirmed by the Senate in September 2025.
Think about that for a second. Kimberly Guilfoyle from The Five is now Ambassador Guilfoyle, stationed in Athens. It’s a massive pivot from debating Greg Gutfeld about New York City crime rates. While she and Don Jr. reportedly hit a rough patch and separated in late 2024, her standing in the Republican party remains solid. She’s currently focused on energy security and trade relations in the Mediterranean, a far cry from the "Fan Mail Friday" segments of her past.
The Kimberly Guilfoyle Timeline:
- 1994: Graduates from USF School of Law.
- 2001: Marries Gavin Newsom (divorced 2006).
- 2006: Joins Fox News after a stint at Court TV.
- 2011: Becomes an original co-host of "The Five."
- 2018: Leaves Fox News amid controversy and joins the Trump campaign.
- 2025: Officially sworn in as U.S. Ambassador to Greece.
What Most People Get Wrong
People often assume she was just a "pundit." In reality, her legal background shaped the way she handled the show. She viewed every segment like a closing argument. That’s why she was so polarizing. You either loved the "prosecutor" energy or you found it exhausting.
If you're looking to understand her impact, don't just watch her old clips. Look at how "The Five" changed after she left. The show became more polished, sure, but it lost a bit of that raw, combative energy that Kimberly brought every single day at 5:00 PM.
Next Steps for Enthusiasts:
If you want to track her current work, keep an eye on the U.S. Embassy in Greece's official dispatches. She's shifted her "The Kimberly Guilfoyle Show" on Rumble to a more diplomatic tone, though she still maintains a massive following in the digital space. For those interested in her legal philosophy, her book Making the Case actually holds up as a decent guide on self-advocacy, even if you don't agree with her politics.