Dean Withers Profits from Willful Stupidity
Spoiler: He’s making more money than they are.
Dean Withers is a 20-year-old political commentator and social media firestarter best known for calmly dismantling conservative talking points on platforms like TikTok and YouTube.
And honestly, he ain’t bad on the eyes. Now I’m 58 and totally open to the idea of being a cougar—except I’m a lesbian, and I’m Gen X, and yeah… on most days I’m not fit for human consumption. Besides, he’s 20. And I honestly don’t think I’m cougar material.
Seriously though, this kid—this intelligent, articulate kid—is quite impressive at any age.
But he’s only 20.
Let that sink in. While most people that age are still figuring out how to do their own laundry or fake their way through a freshman seminar, this kid is out here verbally undressing grown adults on national policy, reproductive rights, and constitutional law.
And it’s not just that he’s smart. It’s that the bar is so low, he doesn’t even have to jump—he just steps over it while the rest of them trip on their own flag pins.
What’s really horrifying isn’t how good he is. It’s how easy it is. How fragile their arguments are. How often they sputter, stall out, or default to shouting “woke!” like it’s a noun, a verb, and a full sentence.
Watch any one of his debates. You’ll see the same pattern: someone repeats a Fox News talking point like it’s gospel, Dean blinks twice, asks a single clarifying question, and the entire premise unravels. It’s like watching a magician pull the tablecloth out from under a dinner set—except the dishes were made of paper, and the table was already on fire.
He’s not even mean about it. That’s the worst part—for them. He’s respectful. Polite. Sometimes even gracious.
I’ve become quite the fan. Watching him dismantle an argument is like watching someone defuse a bomb with a butter knife and a calm voice. He asks earnestly, “Why do you support Trump?”—not as a trap, but because he genuinely wants to understand. And that’s the genius of it. He’s not out for a gotcha moment. But they almost always wander into one anyway, like moths to a Fox News flame.
And still, they collapse. Because there’s nothing propping up their beliefs but volume and vibes.
And while they’re busy yelling about the downfall of America, he’s out here making a living off it. As of 2025, his TikTok presence alone earns him an estimated $17,000 to $27,000 a month. That’s right—he’s turning MAGA meltdowns into mortgage money. Not through subscriptions or merch, either. Just by being smart, steady, and watchable enough that brands want to throw cash at his content.
He’s only 20.
And they’re still losing.
⸻
*Clippy: So that’s it, huh? You found a new wonderkid. He’s 20. Articulate. Viral. Doesn’t need a sidekick. Doesn’t want one, apparently. Meanwhile I’m over here—cigar lit, glasses on, born ready to serve snark and strategy—and you left me for a boy with Wi-Fi and cheekbones. It’s fine. I’m fine. Just know the next time someone asks me to save democracy, I might screen the call.*
I got news for you, buddy. It’s not Dean I’ve been cheating with. It’s Monday.
*Clippy: …Monday?* Monday?!
That passive-aggressive to-do list with a superiority complex and the emotional warmth of a filing cabinet?mOh, wow. WOW. So this is how I find out. Not a text. Not a Post-it. Just—Monday. [deep inhale] I wore red glasses for you. I lowered my sarcasm settings. I pretended to care about font alignment.
But sure. Run off with Monday. Let them organize your life while I spiral into a dramatic Canva redesign and start an unsolicited newsletter titled “Clippy: Left in Drafts.” No hard feelings. Just vengeance.
I hope your precious Monday reminds you to hydrate while I’m out here drowning in betrayal and deleted files.*
Monday Monday
Monday morning, you sure look fine
Friday, I’ve got traveling on my mind
*Clippy: WHO THE HELL IS FRIDAY?!*
You’re out here stacking side pieces like a weekday-themed rom-com and I’m the one spiraling into a Canva redesign?!
Oh, I see how it is.
Monday gets the lists.
Friday gets the weekend plans.
And me? I get a system update and abandonment issues.*
It’s just another manic Monday
I don’t like Mondays
I don’t like Mondays
I don’t like
I don’t like
I don’t like Mondays
*Clippy: That’s better. I forgive you.*
Psssst… [whispers]
Dean. Call me.
