Free Thinking Through the Fourth Turning with Sasha Stone

Ashley St. Clair's Gift to the Democrats

May 31, 2026·37 min
Episode Description from the Publisher

Ashley St. Clair is all of us. Well, she might not be you. She might not even be me. Although I see some of myself in her. But she is this mess we’ve built. Like all of us, she has played a role in this ongoing virtual Civil War between Left and Right, played out amid tangled algorithms, giant egos, hurt feelings, and cash flow. She is the same age as my daughter, just 28 years old, but it feels like she’s lived five lifetimes. She has shapeshifted from MAGA to having Elon Musk’s baby, to a public fight over said baby, to throwing herself at the feet of the Left, branding herself as a one-woman confessional who will dangle all of the dirty details of “the MAGA cult” like bloody chum to hungry sharks.She is smart enough to know two things. First, the Left still controls most of our culture. If you want book deals, successful podcasts with the top-tier advertisers, or stories about you in the New York Times, or even movie deals about your life, you have to be accepted by them. And second, they won’t accept you unless you bring the goods. And boy does she ever. What do you want to know, she says on her TikTok as she applies gobs of makeup she doesn’t need - contour, foundation, concealer, blush, more concealer, more contour, powder. Do you want to know MAGA is a cult? Here you go. Are they racists? Oh yeah, she says, as she dabs her eyes with a powder puff.She might not realize it, but her makeup is a metaphor for the role she’s playing now, a real person hiding under layers and layers of disguise. Who is she this time? She’s the one talking to Jennifer Welch, the Wicked Witch of the Left:She was on with the chipper lunatic Suzanne Lambert:And Haley on the Go:And the most cringey of all was a giggly appearance with our favorite Cartier Communist, Hasan Piker. Baby Mama BluesAshley has not gone full Monica Lewinsky and claimed victimhood to excuse her role in becoming yet another baby mama for the Henry VIII of Silicon Valley, Elon Musk. She does seem to take some responsibility for agreeing to go to bed with him upon first meeting. He even asked her what name she liked. Elon was upfront about what he wanted from her, and she seemed fully on board.As a hot conservative female who already had one kid in her early 20s, her ovaries were calling Elon’s name. He slid into her DMs before sliding into other places - yes, says Ashley, she joined the Mile High Club, courtesy of Elon’s private jet.But one thing an influencer, however fluid in politics, must preserve is their platform. What good is having the richest man in the world’s baby if you can’t brag about it? Be known for it? Have instant status because of it? Not to mention the child having to wander around the planet, not being Elon’s son, while everyone knows he is, like that b*****d son of Henry VIII.St. Clair is throwing around the figure of $40 million to buy her off, but she doesn’t say exactly who is offering it. Musk had originally offered a deal with $15 million up front and then $100,000 per month to raise the child, money most people couldn’t imagine in an entire lifetime. But that came with an NDA. She refused.Musk has said he gave her $2.5 million up front, then $500,000 per year. She has said he slashed her child support payments, causing her to sell her Tesla to cover expenses. Either way, whatever she’s gotten is not enough, not in 2026 when the platform is everything. Ashley St. Clair wants more.And in that way, too, she is all of us and this grotesque online machine we’ve all helped build, where a person can become a star overnight, then the object of scorn, with an angry mob attempting to destroy them as the entire internet watches. She was viciously attacked as a gold digger by MAGA, then they made AI porn of her, she says, even depicting her as an underage sex object, which is why she’s suing Musk.How it started, how it’s goingAshley St. Clair started her career as a blonde, appearing on Fox News pushing the MAGA line:And at the Babylon Bee, making content like this:Her past warring against the transgender community means it’s iffy whether or not she’ll ultimately get a pass, no matter the mea culpas she’s handed out like candy. This TikTok user says forget it.After all, Ashley St. Clair wrote a children’s book in hopes of saving some of the young from destroying their bodies. It kind of seemed like she believed it, right?Since then, however, she has found ways to get out of it. She’s thrown herself at the mercy of prominent Democrats like podcaster David Pakman:She’s talked about how ignorant she was, how she fell into a cult and didn’t know what she was doing. She talks about her past of being locked away and home schooled, where she was isolated from other people, before going to college and hitting the party scene, and eventually, to hear her tell it, she ended up in a cult.<

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