Sugar Daddy Keith Olbermann Roasts His Ex Over Her Tawdry RFK Jr. Fling
The former MSNBC contributor responded to Ryan Lizza’s outing of his past relationship with Olivia Nuzzi.

Jeffrey Ufberg/Paul Morigi/Getty Images
Keith Olbermann, the veteran sportscaster and political commentator, has entered the year’s most tangled and sordid drama in spectacular style with a full-frontal attack on his ex-girlfriend Olivia Nuzzi, the woman at the center of it.
In a series of social media posts, Olbermann, 66, mocked Nuzzi’s “bad” writing, suggested he dodged a bullet, and defended himself over allegations that he served as her de facto sugar daddy.
Another Nuzzi ex, journalist Ryan Lizza, 51, made many bombshell claims in a Substack post circulated on Monday. Among them was the allegation that Nuzzi, 32, also engaged in an affair with Republican congressman and South Carolina governor Mark Sanford, 65—another subject of her reporting at New York Magazine—before she was separated from the company over her relationship with Kennedy.

Keith Olbermann previously described his relationship with Nuzzi as a "wholesome fling."
Frederick M. Brown/Getty Images
When describing Nuzzi’s affair with Olbermann, Lizza wrote that his then-fiancé “felt stalked by Keith after she left him, and we had a strict policy of never engaging with him.” Olbermann was 55 and Nuzzi was 21 at the time that they dated, a relationship that Olbermann has described as a “wholesome fling.” On Tuesday, Olbermann responded to Lizza’s post with several cheeky posts of his own to X, roasting Nuzzi.
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The Daily Beast reached out to Olbermann, but he declined to say more.

Nuzzi's relationship with Ryan Lizza unraveled after the RFK Jr. scandal.
Tasos Katopodis/Getty Images for CBS News
Nuzzi received lavish gifts from Olbermann, Lizza wrote, claiming that Nuzzi “fled her unhappy home in suburban New Jersey and started living with Keith in Manhattan. He paid for her to attend college, outfitted her in Tom Ford and Hervé Léger dresses and some $15,000 worth of Cartier jewelry. Later, he covered her rent and furnished her apartment in a doorman building in the West Village.”
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Olbermann quipped on X in his own defense, “Olivia and I lived together for 4+ years (4 b’days 4 Xmases 4 anniversaries). That’s like $1250 of jewelry per celebration. And her apartment was a studio. And I made an f-ton then. What was I supposed to do? Get her Gift Certificates from Kmart?”
As Lizza had referred to Olbermann as an “older” gentleman, Olbermann posted a refutation of sorts by showing a photo of himself from 2011. Ironically, he is also sporting a cane in the snap. “This is me” back then, he wrote, “and no. The cane is for a broken foot; I was only old, not ‘oldER,’ yet.”
A Nuzzi PS:
— Keith Olbermann (@KeithOlbermann) November 18, 2025
June 2011, CitiField, NYC. This is seven years after this psycho Bobby Kennedy called me up at MSNBC and said I was his hero 🤷🏼♂️This might have been the first sign he was losing his mind
(and no, the cane is for a broken foot; I was only old, not oldER, yet) pic.twitter.com/fr0JyJ1kvy
The more sordid revelation from Lizza’s post, which he saves until the end to reveal, is Nuzzi’s 2020 relationship with Sanford, who was running for the Republican presidential nomination. Olbermann wrote on X, “Ryan Lizza appears to be accusing Olivia Nuzzi of an affair with Mark Sanford when she was covering HIM in 2020?” He added, “This is me,” with a GIF showing Keanu Reeves dodging bullets in The Matrix.
Replied one amused commenter, “Dude, you spent hundreds of thousands on her, you didn’t dodge s--t, lol.”
this is me: pic.twitter.com/cScGAfIeiw
— Keith Olbermann (@KeithOlbermann) November 18, 2025
Responding to another commenter who said Olbermann had “the worst taste in women. First Katy Tur, now Olivia Nuzzi,” Olbermann replied, “You left out Sinema and Ingraham,” referring to the former Democratic Senator Kyrsten Sinema and Fox News host Laura Ingraham. “I’ve been dating since 1974, there have been great women too, you just didn’t know them because not all my choices have been bad.”

Twitter/Keith Olbermann
Olbermann also didn’t hold back his criticisms of Nuzzi’s forthcoming book about her alleged digital affair and ensuing scandal with Kennedy, American Canto. An excerpt of the book was published by Vanity Fair on Monday, and Olbermann made it known that he was not impressed.
Lost in the Nuzzi avalanche is the fact that EVERY criticism of that excerpt is better written than it is 🤷🏼♂️
— Keith Olbermann (@KeithOlbermann) November 17, 2025
“You realize how bad this is, right?” he wrote in reply to the magazine’s social media post promoting the excerpt. He added, “Lost in the Nuzzi avalanche is the fact that EVERY criticism of that excerpt is better written than it is.”
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