Donald Trump Calls Oprah ‘Insecure,’ Challenges Her to Run for President, Has Obviously Lost His Damn Mind

Oprah Winfrey (John Medina/Getty Images)
Oprah Winfrey (John Medina/Getty Images)

So, Oprah Winfrey is (probably) not running for president. We have to make that clear. She is (more than likely) not running!


Of course, she can if she wants to. Because she’s Oprah, and if Oprah says, “Hey, y’all. I want to do this thing,” you don’t say, “No, Oprah, you cannot do this thing you want to do.” Even if you happen to be making Oprah an omelet for some reason, and she says she’d like feta cheese, peanut butter and Frosted Flakes on said omelet, you don’t say, “No, Oprah. That would be terrible idea.” Because Oprah would make it work. And then have you ordering and eating cereal omelets.

Anyway, Donald Trump’s recent tweets, in which he called Oprah “insecure” and challenged her to run against him, might either be the smartest or the dumbest thing he’s done in office.

It’s obvious why it would be the dumbest: Oprah would kick his ass. Now, whether she’d actually be a good president—and whether we’d actually want someone we love to be in that terrible position again—is debatable. But she’d beat the bone spurs out of that motherfucker. I’d say she’d beat him to the white meat, but I think that once you break Trump’s skin, Tang spills out.

So, how, you ask, could this have possibly been a “smart” strategy? Well, if Oprah has no intentions of running (AND SHE ALLEGEDLY DOESN’T), he’s challenging someone he knows isn’t interested in running against him. Like a little brother pushing his big brother, knowing that the big brother (probably) won’t hit him back. Although this is a bitch-ass dog whistle to his base, it does communicate a fearlessness, which they’ll drink up like “MAGA”-flavored Mountain Dew.

But this “show of strength” only matters if he doesn’t get mollywhopped in 2020 by a black woman from Chicago who’s better, smarter and richer than he is. Unfortunately, that’s a moot point. Since she’s (presumably) not running!

Damon Young is the editor-in-chief of VSB, a contributing opinion writer for The New York Times, and the author of What Doesn't Kill You Makes You Blacker (Ecco/HarperCollins)


This is a microcosm of america, right?

A mediocre white man who ended up rich because daddy did illegal shit that was sanctioned by the white establishment... is afraid of a self made black woman who made it to the top 1% despite all the roadblocks said white man and his like put in front of her at every step of the way.

Oh to have the confidence of a mediocre white man..